unusual tours in tuscany

54 Fun & Unusual Things to Do in Tuscany

A destination that has inspired artists, poets, thinkers and dreamers; Tuscany is the epitome of an Italian Eden.

From the countryside to the coastline, its breathtaking landscapes are laden with rolling hills, endless valleys, olive groves, fruit orchards, hilltop towns and sparkling bays.

Escape into the vineyards and sample the most delicious wine in Italy, explore medieval hamlets and relax under the Tuscan sun in a picturesque seaside village.

Boasting a rich history that traces back to the Etruscan civilization (the region’s first people), the architecture and ruins to explore will blow your mind, with structures and facets dating to the prehistoric ages through to the Romans, and of course, the infamous Medici family.

Marvel over stunning cathedrals, antiquated fort walls and palaces decorated in old-fashioned Italian splendor. The art in these parts screams of the Renaissance… See real-life works by masters like none other than Leonardo Da Vinci (who was born in Tuscany), Michaelangelo and more.

Situated in Central Italy, its capital city is Florence and Rome is three hours away. With so many things to do in Tuscany , you’ll wish for at least three days in the region.

Start off by becoming familiar with its cities, villages, towns and parks. Here are some of the best listed below.

1 – Make your first stop Val d’Orcia

Tuscan dreams are made of these and arriving at Val d’Orcia feels like stepping into a picturesque Italian postcard — cue the roads lined with tall cypress trees and rolling green hills.

Situated in the Siena Province between Grosseto, with the Orcia River running through the UNESCO World Heritage Site, the rural and rustic landscapes dotted with farmlands, vineyards, groves and medieval structures date back centuries.

Considered a prime example of the Renaissance periodical features, the agricultural villages around here will take your breath away. Castiglione d’Orcia, Montalcino and San Quirico d’Orcia are towns in the area worth seeing, and of course, Pienza — home to some of the yummiest pecorino cheese you’ll ever taste!

(Whilst in Pienza, don’t miss checking out Pienza Cathedral, Piazza Pio II (the town square) and the Renaissance-style palace, Palazzo Piccolomini.)

A foodie hotspot too; indulge in tasting the best extra virgin olive oil, truffles, saffron, olives, chestnuts, wine and cheese from the region, and cheese and wine tastings are popular during Orcia Valley tours from Florence .

Other bucket-list sites to discover in Val d’Orcia include the iconic Cipressi di San Quirico d’Orcia (San Quirico cypress trees) and the lonely Cappella della Madonna di Vitaleta, i.e. Chapel Vitaleta.

2 – Stay, explore, and eat your way through Florence

It’s funny how many think that Tuscany is part of Florence, when in fact, it’s the opposite way around for the capital city of the region, but who can blame you when there are endless things to do in Florence ?

Established by Julius Caesar circa 59 BC, it was during the 15th and 16th centuries amidst the Medici reign that Firenze (as it’s also known) garnered its famous status as a city of artists, birthing the Age of the Renaissance.

Today, thousands flock here to run their hands over antiquated buildings and landmarks and to revel in a world of art and wonder. Erected between 1296 and 1436, visit the Florence Duomo (Florence Cathedral) and the other buildings within the religious complex including St John’s Baptistery; spot the Donatello statues around the city and explore the Uffizi Gallery where work by Leonardo Da Vinci, Raphael and Michelangelo is on display.

Other historic sites to add to your sightseeing itinerary are Piazza della Signoria, Santa Maria Novella church, the Basilica of Santa Croce and the Ponte Vecchio , i.e. the Old Bridge, crossing the Arno River.

There are many other great museums in Florence like Dante’s House Museum, the Accademia Gallery and the Palace of Bargello, or get involved in other cultural tours and activities in Florence.

Hit up the iconic San Lorenzo Market (the best place to buy leather goods); catch a live concert of your favorite international artist or band with Firenze Rocks and embark on food tours for a true taste of the capital city.

• Tours & Activities in Florence

3 – Bathe in the healing waters of Saturnia

Keep your camera close on hand for a trip to Saturnia where terraces of milky-colored hot springs cascade into pools surrounding stone houses and in between wild sun-kissed shrubbery.

A designated hot spring locale (that not many know about) within the Maremma region, Saturnia itself is a tiny ancient town with its origins dating to 60 BC. Its earliest settlers can be traced to the Greeks, then the Etruscans, followed by the Romans and it’s intriguing to witness the amalgamation of styles in the village.

Scope out the Aldobrandeschi Fortress, the Santa Maria Maddalena church and the Archeological Museum for in-person timelines. However, it’s the natural thermal pools that visitors come to marvel over and there are a few in the area, some open to the public, others forming part of spa resorts.

Comprising seven geothermal pools and a waterfall, Cascate di Mulino is the most popular as it’s free and open to all.

Terme di Saturnia is another hot spring, but this one is part of a private resort — an idyllic destination for couples. The property boasts a main hot spring pool reaching temperatures of 37.5 degrees Celsius and its Thermal Park is right next door to the stay. There are five thermal pools here.

4 – See the famous parade in Viareggio

Swap countryside terrains for a coastal setting down at the seaside resort town of Viareggio — but it’s not its beaches that have put it on the map, but rather its famous Carnival!

Located in northern Tuscany and forming part of the Versilia Riviera, the town boomed as a fishing village centuries ago and then later a holiday hotspot.

With its origins in the 11th century, there are plenty of historic buildings and places of interest to hunt down, and during the latter centuries, a slew of modern Art-Deco-style structures popped up around the city, for example, the Villa Argentina and the Villa Paolina.

Investigate the Alberto Gianni Maritime Museum and take a stroll along the Viareggio Promenade where dozens of cafes, boutique shops and bars line the cobbled streetways, including the famous Gran Caffè Margherita.

Since 1873, the annual Carnival of Viareggio has colored the city streets where tons of artsy floats and masks made from paper mâché parade through town.

To commemorate the globally-recognized folk festival, the La Cittadella del Carnevale complex opened in 2001. The Viareggio Carnival Museum is here too with some of the coolest paper mache creations on show, along with a bookshop and paper mache workshops.

5 – Make Lucca your base in northern Tuscany

Travel back in time when visiting historic Lucca — famed for its ancient walls preserved in the old town.

From the Romans to the Renaissance era, fourth times the charm, and the final construction of the Lucca walls was between the 17th and 19th centuries. Enrwapping the old town for 4.2 kilometers, the fortified ‘Mura di Lucca’ holds the title of one of the best-kept city walls in Europe.

Among the things to do in Lucca, you can walk the entirety of the walls along a footpath that connects 11 stone and brick bastions. The city itself was founded by the Romans in 180 BC, and its rich history is heavily admired, evident in the varying structures and monuments from different eras.

Explore Piazza dell’Anfiteatro (once a Roman amphitheater-turned-town square in later years), climb 230 steps to the top of the 45-meter-tall 14th century Guinigi Tower; and imagine life in the early days when exploring the many churches, cathedrals and towers.

As the birthplace of Italian composer Giacomo Puccini, the Puccini Museum is dedicated to the life of one of Italy’s most famous musical geniuses. Furthermore, if you’re here in July/August, don’t miss the annual Puccini Festival — celebrating some of Puccini’s greatest opera performances.

Another epic festival held every year is the month-long Lucca Summer Festival where international acts are the stars of the show like Robbie Williams, Placebo, Norah Jones and Kiss.

Located at the foothills of the Apuan Alps, make the town your base or visit on a day-trip, for example, during Lucca tours from Florence or Lucca tours from Livorno .

• Tours & Activities in Lucca

Read more: Fun things to do in Lucca .

6 – Relive childhood dreams at Collodi

Feel the magic in the air in the teeny hilltop town that inspired one of the greatest children’s stories of all time; Pinocchio.

Published in 1883 by Italian author Carlo Lorenzini (who changed his penname to Carlo Collodi), the storyline chronicles a woodcarver named Geppetto who lived in a tiny Tuscan hamlet, making a wooden puppet that comes to life.

Carlo Lorenzini’s father worked in the grand Villa Garzoni, and it’s believed that the village inspired the tale that led to The Adventures of Pinocchio.

Adding extra authenticity, visit Pinocchio Park with its interactive museum and themed rides and attractions. The 17th-century Villa Garzoni and its manicured Italian Garden are located here, as well as the Collodi Butterfly House.

Considered a medieval village, the town itself is minute, with houses and narrow stone streets built upwards into the hills. The Antica Rocca (ancient castle) acts as a fortress to the start of the hamlet and Collodi is in the Lucca region.

7 – Day trip to San Miniato

If you’ve chosen the capital city as your base for Tuscany, the town of San Miniato is an excellent stopover in between a day trip from Florence to Pisa.

Arrive for the world-class valley views, historic architecture and… white truffles (famous to the area)!

Built across three separate hills in between the Egola and Elsa Rivers, the origins of Etruscan and Roman civilizations are evident throughout its forts, towers, cathedrals, churches and museums.

Named after a Roman Emperor, the Rocca di Federico II tower was erected between 1217 and 1223, then later destroyed during WWII and rebuilt in 1969. Climb a set of stairs to the top for stunning vistas of the town, Arno River and sweeping vales below.

Other important landmarks to check out here include the 13th-century Cathedral, Piazza del Seminario, the Cathedral of Santa Maria Assunta (built in the 12th century), the Diocesan Museum of Sacred Art of San Miniato and the Conservatorio Santa Chiara (the Santa Chiara Conservatory).

In recent years it’s become a popular destination for leather work, as well as truffle hunting , foraged in the nearby forests, and don’t miss the annual National White Truffle Exhibition in San Miniato if you’re here in November time.

8 – Tick UNESCO-listed Pisa off your itinerary

A place that needs no introduction; Pisa is a bucket-list spot for many travelers, sitting on the west coast of Italy at the mouth of the Arno River. Thinking of things to do in Tuscany? This one is a no brainer.

Laden with UNESCO Heritage sites, the things to do in Pisa are incomparable to many other towns and villages around Tuscany, most notably its Leaning Tower of Pisa , and fun fact; the city of Pisa itself is dubbed a university town and the prestigious University of Pisa is here.

Kick things off at the Piazza del Duomo (nicknamed the “Square of Miracles”) where four of the most prominent landmarks sit.

These include the Romanesque-style Cathedral of Pisa (established in 1064), the stunning Pisa Baptistery of St. John constructed completely from marble between 1152 and 1363, the Museo dell’Opera del Duomo (opening in 1986) and of course, the world-famous Leaning Tower.

Climb 273 steps to the top of the 56-meter-high bell tower — right next door to the cathedral — which took around 200 years to build. Its famous leaning frame is due to soft ground shifting underneath its surface which began moving five years into construction, hence its tilted appearance.

Stroll along the Arno River, visit the museums (for example, the Opera del Duomo Museum and the Sinopie Museum) and pass by the Piazza dei Cavalieri with its Clock Palace.

There are Pisa tours from Florence (Florence is a 1.5-hour drive away) as well as half-day Pisa tours from Livorno (30 minutes from the city).

• Tours & Activities in Pisa

Read more: Fun things to do in Pisa .

9 – Explore the Apuan Alps Regional Park

If you’ve drunk enough wine, eaten way too much and explored the endless antiquated landmarks, revel in a day (or couple hours) out in nature, tackling the hiking trails (which open for ski-time in winter season) and arid terrains inside this UNESCO Global Geopark.

Bordering 19 municipalities (including Versilia, Castelnuovo di Garfagnana, Fivizzano and Montignoso) between Lucca and Massa Carrara, the Apuan Alps Regional Park is every adventure-loving soul’s dream.

Favored for its unique biodiversity, trekking inside Parco Alpi Apuane opens up to a world of unique fauna (spot golden eagles, roe deer and foxes) and flora like beech and oak trees, chestnut groves, and of course, the Apuan Alps.

The main mountains within the regional park are Monte Corchia, Monte Pisanino, Monte Cavallo, Monte Tambura, and Pania della Croce.

Looking around your surroundings expect a vision of marbled quarries, rugged hillsides, lakes (like Lago di Isola Santa) and an extensive collection of 1,300 caves!

There are three caverns open for guided tours. Antro del Corchia (in Levigliani) is the most frequented and well-known and is located in Corchia Park with over 20 different entrances into the cave system comprising 70 kilometers!

Explore the karst caves at the Grotte di Equi Terme (Equi Terme Caves) with a world of activities, or check out the Grotte del Vento in Fornovolasco.

Orto Botanico delle Alpi Apuane “Pietro Pellegrini” botanical garden is a fabulous place to start!

10 – Visit the famous Montecatini Terme spa town

It’s time to relax and rejuvenate in the romantic town of Montecatini Terme where thermal baths are a first priority in one of Italy’s top five spa towns.

Also referred to as the Parc des Thermes, this is one of those places to get a true sense of what Roman life was like back in the day, however, it was only later on in the 18th century that the first spa complexes open to the public began taking shape.

The healing, naturally heated waters in these parts are mineral-rich, and not only can you enjoy a restorative soak, but you can drink the water too.

Today, there are public spa baths as well as dozens of spa hotels that contain their own private thermal baths for guests.

Utilizing waters from the Tettuccio, Regina, Leopoldine and Rinfresco springs, the Excelsior Thermal Complex is at the center of Montecatini. Inside the complex is Terme Tettuccio — which focuses on water-drinking therapies — and the indoor Terme Redi baths where you can soak in waters heated to 33 degrees Celsius.

Other activities in Montecatini Terme to try include riding the old-school Montecatini Funicular up the hill to the medieval village, Montecatini Alto, exploring Grotta Maona (a karst cave roughly one kilometer from the town center) and shopping Montecatini Market or its fancy boutique stores.

• Tours & Activities in Montecatini Terme

11 – Watch motorsports in Scarperia e San Piero

Just 25 kilometers northeast of Florence discover one of Tuscany’s latest towns, only established as a municipality in 2014! Prior to this, Scarperia e San Piero was two separate neighborhoods, each a medieval village but the two converged together a decade ago.

Situated in the Mugello countryside, Scarperia and San Piero now act as one and the town is a treat for architecture aficionados.

Around the Scarperia areas check out 14th century Palazzo dei Vicari (the main square), then head to the banks of San Piero and visit the Parish of San Pietro and the Medici ‘Villa del Trebbio.’

Chefs and avid home cooks; Scarperia is also famed for its knife-making or motorheads, the revered Mugello Circuit is in Scarperia e San Piero — home to the Italian Grand Prix!

Busting its first races back in 1914, you can catch all sorts of motorsports along its 5.2-kilometer-long track like car and motorcycle races, and events are held here throughout the year.

12 – Go wine tasting in Chianti

Honeymooners, couples in love and wine connoisseurs… Chianti is calling your name, located in the heart of Tuscany and known for its famous wine region . The most fabulous experiences for wine tasting in Tuscany are right on your doorstep…

Picture unending green rolling hills, valleys dazzled in vineyards, stone farmhouses, dreamy villas and town-cobbled streets with plenty delicious eats that go down well with a glass of vino.

(Note, Chianti is a region between Florence and Siena and there are multiple day trips from Florence as well as Chianti tours from Siena to this unreal locale.)

The main towns around the region encompass Greve, Castellina, Radda, Gaiole and Panzano.

Spend your day touring the vineyards, lapping up cheese and wine pairings, and going behind the scenes and into the cellars to learn about the manufacturing process from grape to bottle during the best Tuscany wine tours . There’s even a wine resort; Meleto Castle!

Notable wineries include Castello di Brolio, Castello di Querceto, Fattoria di Montecchio and Viticcio winery. As one of the most visited parts of Tuscany, there are Chianti tours from Livorno , Lucca and Pisa .

• Tours & Activities in Chianti

Read more: 17 Best Chianti Wine Tours from Florence to Discover the Heart of Tuscany ,

13 – Check out famous frescoes in Prato

Welcome to Tuscany’s second biggest city — a mere 30 minutes outside of Florence — where its historic center is a treasure trove of the kind of historical and culturally enriching findings that make you fall in love with the very essence of Europe.

Castles, forts, towers and frescos date to the long-forgotten Etruscan and Medieval times such as the Castello dell’Imperatore built between the years 1237 and 1247, and the grand Medici Villa La Magia.

Tour the inner city starting at St. Stephen’s Cathedral (the masters Donatello and Michelozzo designed its pulpit and inside contains frescoes by Filippo Lippi) and its plaza in front of the church.

Enjoy a moment around the Fontana del Bacchino fountain, and inside the Medieval Palazzo Pretorio is the Museo di Palazzo Pretorio with works by many famous Italian artists.

More historic sites worth investigating are the Church of San Francesco, the Emperor’s Castle, Santa Maria delle Carceri, the Church of San Domenico and the Museum of Mural Painting.

14 – Wander in the same footsteps as the genius in Vinci

Any guesses as to where the town of Vinci gets its name? As the birthplace of one of the greatest artists to ever live; Leonardo da Vinci , the small Tuscan municipality of Firenze is centered around all things Da Vinci.

With undulating banks of olive groves as a backdrop, it’s what’s in the town that counts. Fall into a world of mechanics, design, art and history as you not only unravel real works by the master, but also get to take an introspective look into the life of the inventor, architect, technologist, artist and man of the Renaissance.

Head directly to the Museo Leonardiano di Vinci (the Leonardo da Vinci Museum) which is spread out and set up between two main buildings: the Conti Guidi Castle and Palazzina Uzielli.

The primary theme inside the Palazzina Uzielli building is ‘Leonardo the Technologist and Engineer’ with video installations, and focuses on machinery, textile technology, mechanical clocks and anatomical studies.

His interests in war, architecture, mechanics and flight are highlighted inside the Castle and include sections dedicated to his landscape drawings, interest in hydraulics and his childhood.

Three kilometers from Vinci center is the farmhouse where Da Vinci was born in 1452 and grew up as a child, with projections, exhibitions, recreated scenes and his life’s story displayed in his childhood home.

In summertime, the biggest fantasy festival in Italy is held here, Festa dell’Unicorno , and dressing up as fairies, elves, and all sorts of mystical creatures imaginable is encouraged.

• Tours & Activities in Vinci

15 – Get romantic in San Casciano in Val di Pesa

Welcome to the gateway to the Chianti Region, conveniently situated a short 15 kilometers to the south of Florence, and San Casciano in Val di Pesa was once one of the major roads for traveling between Florence, Siena and Rome.

Centuries ago it operated as a small trading village, but the city of Florence employed it as an extra defense force in the 15th century, when its stone brick city fort walls were erected.

Very local and steeped in traditions, it’s the art, food and culture you’ll most want to enjoy.

Inside the Giuliano Ghelli Museum (located at the Church of Santa Maria del Gesù) are three primary exhibitions: the sacred art collection, contemporary art and an archaeological section.

The 14th-century Church of Santa Maria del Prato is another spot that houses a wonderful art collection by acclaimed artists.

En route to Chianti, break here for a caffè, and grab a gelato or light lunch at a traditional trattoria.

Couples, hot air balloon rides in Tuscany swoop over the quaint town, boasting bird’s eye angles of the Chianti Region below.

16 – Explore the tower city of San Gimignano

Spot San Gimignano from a mile away — all you have to do is look out for the tall towers on the hillside stretching up toward the heavens.

Considered Tuscany’s “tower town” this is every architecture admirer’s dream with its impressive 13 fourteenth-century towers remaining, as well as medieval palaces and excavated structures and remains dating to the year 63 BC during the Roman Conquests.

From a booming trading town to a general decline in economic freedom, the city has an interesting past. 13 of the 72 original towers (erected by the elite of the city as a symbol of their wealth and power) remain.

Examples are Torre Grossa (the tallest of the towers), Campanile della Collegiata (known as the Bell tower of the Collegiate), Torri degli Ardinghelli, Torre dei Becci, Torre Campatelli, Torre Chigi, Torre dei Cugnanesi, Torre del Diavolo (Devil’s Tower) and Torre Ficherelli.

The Duomo of San Gimignano is another piece of impressive medical architecture, and visitors are always blown away by the friezes, frescoes, paintings, altars and chapels inside.

Day tripping from Florence (55 minutes away) or Siena (a 40-minute drive) get to explore over 10 churches and cathedrals, its civic museums and even ancient ruins just outside of the city.

There are San Gimignano tours from Pisa and Livorno , and take advantage of the local fresh products in this UNESCO World Heritage Site.

• Tours & Activities in San Gimignano

17 – Venture around the Apuan Riviera

As temperatures soar to up to 40 degrees Celsius in Tuscany during the peak of summer, beat the heat along the Apuan Riviera extending for 20 kilometers towards Liguria.

Found between the Versilia Magra Rivers with the Apuan Alps in the background, the calm shoreline sits on the Tyrrhenian Sea, becoming a hotspot for water activities and lazy beach days from around April to September.

Interior designers, the sought-after Carrara marble hails from this area, and you can enjoy exciting jeep tours to the heart of the white marble quarries in Colonnata, or embark on a bike excursion here instead.

The main Carrara quarries to explore are Fantiscritti, Gioia, Torano and Ravaccione, and photograph super cool modern “street art” illustrated around the spaces.

There are a few museums worth visiting that shine a light on marble art and history, like the unmissable The CARMI – Carrara and Michelangelo Museum, the Civic Museum of Marble and the Gigi Guadagnucci Museum .

Hoping to spend the night? Marina di Massa is the perfect base sitting on the coastline. Go fishing off of the Pontile di Marina di Massa or feast on the freshest seafood. Speaking of food, don’t miss sampling Colonnata lard — procured right here in Colonnata.

Other popular cities in the region to explore (or stay at) are Antona and Montignoso.

18 – Canyon in Garfagnana and Mid Serchio Valley

Why not choose the road less traveled? Navigate your way to an area between the Apennines and the Apuan Alps where the Garfagnana region sits — with the Serchio River crossing its lands.

Thanks to its location amidst the Mid Serchio Valley, this part of Tuscany truly feels worlds away and is considered one of the country’s most exquisite hilltowns with plenty of villages to explore and outdoor adventures to be had from hiking to biking.

Dating to the Romans and boasting heavily Medieval-influenced buildings, Barga is a perfect town to start in (or stay over). Meander the cobbled streets, spend hours photographing ancient walls and piazzas, and there are a handful of artisanal boutiques in town.

Next, discover Borgo a Mozzano village and its famous Ponte della Maddalena (also known as the Devil’s Bridge), then make your way into the capital of Garfagnana and explore Castelnuovo Garfagnana.

Abandoned Vagli di Sotto and Coreglia Antelminelli (home to the Museum of Plaster Figurines and Emigration) are worth visiting too.

Surrounded by ravines and lakes, top nature spots to inspect are the wind caves, i.e. Grotta del Vento , Strette di Cocciglia where you can go canyoning down its limestone formations, or make your way to nearby Lucca and enjoy rafting on the Lima River .

19 – Witness the famous horse race in Siena

It’s safe to say that the UNESCO World Heritage Site city of Siena is an architectural masterpiece in its own right, with Italian cities and other European countries taking influence from its (painstakingly preserved) Gothic structures and design, used as inspiration by many artists.

Thousands flock to the historic destination to scope out the special medieval city built within its Piazza del Campo walls. The seven-kilometer-long fortification was established over three Tuscan hillsides, connected by three main streets, creating its Y-shaped piazza.

If parts of the city look familiar it’s because its famous Palio di Siena was featured in the 2008 James Bond movie, Quantum of Solace .

Held annually in the Piazza del Campo since the 6th century, this historic horse race takes place on July 2 and August 16 where various Senese areas (known as contrades ) compete against one another.

Among the things to do in Siena, dedicate a couple of hours to investigate the 17 city districts and monuments, including the Piazza del Duomo, the Pubblico Palace, the Duomo di Siena and the Santa Maria della Scala museum.

Search for the famous sword of Galgano stuck into a stone which remains intact inside the San Galgano Abbey (Abbazia di San Galgano), and day trips to Siena from Florence (one hour away), Livorno and Lucca (1.5 hours away) are some of the most popular tours in Tuscany.

• Tours & Activities in Siena

Read more: Fun things to do in Siena .

20 – Appreciate the serenity surrounding Chiusi della Verna

Catholics, religious devotees and even lost souls; discover a moment of silence and deep contemplation when traversing to Chiusi della Verna — famously known as the place where Saint Francis of Assisi received his stigmata, and for centuries, it has been a pilgrim destination for many.

Located inside the Casentinesi Forests National Park, the atmosphere is always extra fresh — with snow covering its land in winter — and beech and fir trees grow in abundance surrounding the hamlet.

Built on top of Monte Penna, the La Verna – Franciscan Sanctuary is where Francis ‘met’ God and his miraculous crucifixion wounds appeared.

Uncover art and a museum at the Sanctuary of San Francis, and in front of the monastery is the Church of San Michele Arcangelo and the ancient Castello dei Cattani.

There are annual events and festivals that happen in the village as well as surrounding areas. In August, don’t miss the craft market or truffle and mushroom festival, and every July the International Festival of Organ Music is set up in the Sanctuary.

21 – Enjoy Livorno’s salty air

Established by the Medici family as a port city in 1606, Livorno is a melting pot of culture, trade and delectable foods.

Flooded with canal systems and bridges, it’s garnered the nickname “Little Venice” and straddling the Tyrrhenian coast, it has a distinctively different atmosphere to most places. Plus, munch down on some of the best and freshest seafood!

Tuscany’s third-largest city forms part of the Livorno Region (sharing the same name) and is just a 15-minute train ride from the famous Pisa.

As such, the city is also favored as a landing dock and entry point for travelers arriving from other regions around Italy via boat.

Embark on wine tasting tours from Livorno to the nearby town of Bolgheri, or flit around the city and trek down must-see monuments and landmarks.

Stroll along the black and white checkered Terrazza Mascagni square promenade overseeing the ocean; visit the Old Fortress (i.e. Fortezza Vecchia) and float past the Fortezza Nuova (New Fortress).

Just outside of the main city is the Sanctuary of Montenero religious complex, opening less than 30 years ago in the Montenero Livorno Hills.

• Tours & Activities in Livorno

22 – Get your winter sports on in Pistoia

Ever-changing with the seasons, no matter what time of year you visit Pistoia far up north, you’re blessed with breathtaking natural scenery!

As the capital city of the Pistoia Province, get your fix of historical sightseeing before venturing further inland to explore its surrounding Pistoia Mountains decked with many winter activities.

Awarded the title of Italian Capital of Culture in 2017; eat, drink and gallivant your way through the town’s must-see attractions, restaurants and cultural events.

Pilot your way underground the dug-out passageways of the 13th-century medieval Ospedale del Ceppo hospital, examine the monuments around the Piazza Del Duomo town square, bring the kids to the Pistoia Zoo and grab lunch from a cafe or trattoria around the bustling Piazza della Sala.

The Pistoia Blues festival and the Pistoia Dialoghi sull’uomo (Dialogues On Man) event are held here annually.

Leave behind the city feels and adventure into the Pistoia Mountains (running from the Alpe delle Tre Potenze to La Croce), dotted with traditional villages. On the eastern side, ski resorts open up in winter, such as Doganaccia 2000 and the Abetone Val di Luce skiing area.

23 – Keep your eyes peeled for “vampires” in Volterra

Ladies and gentlemen, introducing the oldest city in all of Italy, it’s none other than ancient Volterra where one footstep inside the antiquated town will pull you back in time before most of the world even formed!

Fascinatingly, it’s now one of the smallest-populated towns, but that doesn’t tear away from its historical significance.

Situated in the province of Pisa, it’s one of the first places where Etruscan civilizations began and much of this early Italian empire remains evident within the city walls.

(The Etruscans hailed from Etruria — what is now most of Tuscany — ruling between 900 to 500 BC. The Roman empire period proceeded it and so the city boasts an amalgamation of both eras.)

Founded in 1761, the Volterra Etruscan Museum “Mario Guarnacci” is a fantastic starting point, then move to the Piazza dei Priori (Tuscany’s oldest town hall).

Uncover Roman Ruins at the Roman Theater which was built in the 1st century CE and investigate the remains of the 4th-century Roman baths (behind the amphitheater).

During day trips to Volterra from Florence or Siena , be guided to the old Etruscan Walls and its six fortified entrance gates, tick the Etruscan Acropolis off of your bucket list and mosey around the Medici Fortress for the best views of the city.

• Tours & Activities in Volterra

24 – Ride up the hill in Certaldo

The picturesque setting of Certaldo town — whose homes and buildings flit up a hill — is a stand out from the rest, and unlike most of the cities and villages around Tuscany, this one is void of a town square.

The result? The monuments and sights to see all scrape the edges of the main narrow street that acts as the center of Certaldo.

Whilst its origins date to the Romans, the town is divided by two parts: the old town (known as Certaldo Alto) and the new Certaldo (referred to as Certaldo Basso).

At the very top of the high-rising hill is the ancient part of the city — make sure you wear comfortable shoes as you’ll be doing some walking, or alternatively catch a funicular ride to the top.

Points of interest to sweep through here are the Palazzo Pretorio (situated at an intersection of the two main streets, Via di Boccaccio and the Via del Rivellino) and run your hands along the Porta Alberti, Porta al Sole and Porta al Rivellino fort walls.

Certaldo Basso sits toward the bottom of the hilltop and is home to the famous Boccaccio’s House museum where the acclaimed 14th-century poet, Giovanni Boccaccio lived for many years, as well as the Ente Nazionale Boccaccio chronicling his life and work.

If you’re visiting here in July, don’t miss the Mercantia street art festival . Running for 34 years and counting, it’s a celebration of creativity and a night market pops up too during the event.

25 – Hike to waterfalls around Colle di Val d’Elsa

Bohemian souls; find yourself dazzled by the local craftsmanship and art in the charming town of Colle di Val d’Elsa — literally translating to the ‘valley above the Elsa River.’

Flashback to the end of the 16th century and the art of crystal glass-making began booming in this town. Today, it’s still the country’s largest mass producer and the Museum of Crystal is totally worth checking out for a deeper understanding of the trade, as well as to scope out some of the coolest works made completely from crystal.

The Civic Museum of Sacred Art (also known as the San Pietro Museum) and the Ranuccio Bianchi Bandinelli Museum archeological museum are also worth popping into.

Don’t end things with a tour of the town, rather head into its gorgeous surroundings, specifically Parco Fluviale Alta Val D’Elsa below the town. Here is the four-kilometer Sentierelsa Trail leading you through a forestry of streams and wispy trees along the Elsa River.

Eventually, you’ll end up at the 15-meter-high cascading Diborrato Waterfall with its breathtaking turquoise blue waters… Keep your camera close by!

26 – See the ancient jousting sport in Arezzo

Another town used as a filming location in Tuscany (this time for the local Oscar-winning 1997 blockbuster, Life is Beautiful , or ‘La vita è bella’), Arezzo is the perfect fusion of old-meets-new Italy, and it’s often compared to Florence because of its similar city outlay and buildings, as well as its art-focused offerings.

Opening every first Sunday and last Saturday of the month, pick up treasures from The Antiques Fair (one of the oldest of its kinds in Italy); stand in awe at the Basilica of San Francesco where the famous Renaissance frescoes by Piero della Francesca cover the walls, and people watch whilst sipping on Italian coffee in the Piazza Grande square.

This Tuscan town is separated by its old and new districts, brimming with Medieval and Renaissance styles.

Add the Casa Vasari (with its collection of Mannerist paintings), the National Museum of Medieval and Modern Art, the 12th-century Santa Maria della Pieve church and the compelling Medici Fortress Park to your Arezzo itinerary.

An event not to be missed; during the months of June and September, the Saracen Joust festival pays homage to the ancient sport where live jousting is the main attraction!

• Tours & Activities in Arezzo

27 – Meander through the castle town: Poppi

Located in the Arezzo Province and close to Arezzo city, enjoy a day trip to Poppi and travel back to the Middle Ages when wandering the stone staircases, passageways and once-grand halls and rooms inside the Castle of the Counts Guidi.

Constructed by the Guidi family in 1274, it’s the main attraction in this sweet little hamlet, and the village is situated inside the Casentinesi Forests National Park… Its surrounding landscapes are super pretty!

Steeped rich in medieval history, hunt down the Rilliana Library containing medieval manuscripts and about 700 incunabula; the courtyard leading to the protective city walls and marvel over the 13th-century frescoes inside the Chapel of Conte Guidi.

More stunning landmarks to visit are the Baroque-style Oratorio della Madonna del Morbo church and the San Fedele abbey.

Close to Poppi and worth your while to visit whilst in the area, spend an hour or two at the Camaldoli Hermitage monastery and the Chestnut Ecomuseum in Ortignano Raggiolo (15 minutes from the village).

28 – Discover a different side of Tuscany in Sansepolcro

Nestled in the Valtiberina Valley, Sansepolcro rose to fame as the birthplace of Early Renaissance Italian painter and mathematician, Piero della Francesca!

As such, art reigns supreme in the city, and there are plenty of places to admire this famous artist’s work.

Start at the Museo Civico di Sansepolcro (Civic Museum) housing four of Francesca’s paintings including the famous ‘The Resurrection,’ and the museum itself is a beautiful building worth exploring.

Working at the Cathedral of San Giovanni Evangelista (also called the Duomo of Sansepolcro), the artist’s body was buried inside its chapel upon his passing in 1492.

However, that’s not the sole reason why tourists love the mysterious ancient town, and bordering the Umbria and Marche regions, its terrains and buildings differ from the rest of Tuscany.

Displaying collections of ancient herbs, laboratory tools, ceramics, mortars, glassware and ancient books detailing medicinal plants, the Aboca Museum is epic!

The Bernardini-Fatti Museum of Antique Windows is another fascinating stop and search for the bronze statue of the Adele and Ginna Marcelli sisters who made lacemaking a recognized pastime.

29 – Pretend to be the Cullens in Montepulciano

Attention die-hard Twilight fans; walk in the footsteps of Bella and Edward during an exciting trip to Montepulciano where there are even special Twilight tours available!

Fun fact: The Italian scenes for the sequel, The Twilight Saga: New Moon were all filmed in the city (even though in the books and movies the Volturi coven technically live in Volterra — also in Tuscany, the actual city is one hour and 45 minutes away).

Twilight business aside, Montepulciano has a real regal feeling about it, with classic Renaissance-style palaces bountiful, grand squares with cobbled corner cafes, vineyard views and wine tastings.

With the Val d’Orcia and Val di Chiana valleys framing the town, you have to try the region’s famous red Vino Nobile — a prized grape around the world. Naturally, it’s a perfect base to go wine tasting around the treasured vineyards with an option to tour via ebike!

Head into the cellars and indulge in vino and cheese pairings too. You’re in Italy after all…

Add the 13th-century fortress Fortezza Medicea and historic Porta al Prato city gate to your must-see landmarks during day trips from Florence (1.5 hours by car) or Siena (under one hour away).

• Tours & Activities in Montepulciano

30 – Don’t overlook Anghiari

Ask any local about the Battle of Anghiari and they will tell you the story with pride! Occurring on June 29, 1440, it was this monumental crusade that helped keep the Republic of Florence (and the lower Tuscany region) a separate state back then from Milan.

For art historians and curators, they might answer differently… Fascinatingly, a painting by none other than Leonardo Da Vinci depicted this battle but it’s believed (and argued) to have gotten lost in the centuries. It’s also known as ‘The Lost Leonardo’ and some believe the painting never even existed!

More to the medieval village than just that, photograph its pointed stone tower tops and houses with vineyards and iconic Tuscan hills acting as the best backdrop!

Wandering down its narrow stone streets you’ll see artisans selling woodwork, textiles and gorgeous ceramics, and snap dozens of photographs of intriguing ancient homes made ever more eclectic and eye-catching because of their somewhat “derelict” features.

Piazza Mameli is the major town square where the Renaissance-style Palazzo Marzcocco and the Medieval-style Palazzo Taglieschi both stand.

31 – Dive into the world of scuba… literally!

While this region may not be the most famous scuba center, it certainly offers its own underrated charms!

And with such clear, gentle waters, it’s easier than ever to learn this addictive sport!

Plus, with amazing scenery and cool wildlife, you’ll find wonders on even the shortest dives!

• scuba diving in Tuscany

32 – Admire Monteriggioni

Closed off by fort walls built in a circular shape, all of the buildings and landmarks that have been erected within Monteriggioni work in perfect harmony in Tuscany’s “walled city.” Even the road circling the town winds around the village.

The teeny hamlet dates back to the Middle Ages and its tall ancient medieval fortifications still enshroud the city today. This makes it feel like you’re really in worlds before your time — like way, way back!

Situated in the Siena Province, the masses flock here on day trips from Florence (or enjoy Monteriggioni tours from Siena if this is your base) for the chance to see the captivating setting.

Built as a castle, its archaic defense towers and fort walls are the main attraction and you can traverse the walls along a walkway even climbing up certain parts!

The annual July Monteriggioni Medieval festival is one of the most authentic in all of Italy!

33 – Follow the Tuscan sun in Cortona

This is one of Tuscany’s must-visit hilltowns situated in the south, and it never fails to win over every romantic’s heart.

Stroll through narrow streets and alleys where cobblestone houses are designed on a slope, intersecting one another, and the likes of bright red doors or blue shutter windows stand in stark contrast.

Plus, with the filming of the movie Under the Tuscan Sun taking place here, you can only imagine how dreamy the locale is.

Visit the main Piazza della Repubblica in the middle of the historic center and scope the landmarks here like the Palazzo Comunale, the Palazzo del Capitano and the town clock tower.

The city’s rich history stretches far back to the earliest days in Italia, and evidence found by historians points back 2,000 years ago with some of its first settlers, the Etruscans.

Deep dive into its past at the gorgeous, old-school MAEC – Museum of the Etruscan Academy (also called the Etruscan Academy), profiling and exhibiting collections starting from the 2nd century BC. Swap artifacts for artwork and check out the Diocesan Museum filled with religious paintings, frescoes and motifs.

Cortona tours from Florence always make sure to stop over at the Fortress of Girifalco (Fortezza del Girifalco) as well, and the fort walls have stood the test of time since the earliest centuries.

• Tours & Activities in Cortona

34 – See a town carved from stone in Sorano

There is so much about Sorano that makes it so fascinating, captivating many curious travelers when they hear of its ancient history and unique makeup for Tuscan standards.

Perched on a hilltop, the entirety of the ancient city was built out of stone, well, a type of rock known as ‘tuff’ which forms from volcanic ash, garnering the nickname “The City of Tufo.”

Sometimes referred to as “the Matera of Tuscany,” similarly Sorano appears carved out of the earth.

Its past is as historic as they come, and before the Etruscan people, its earliest civilization links to the Villanovans from the Iron Age. As you can expect, the landmarks, monuments and points of interest here are some of the most venerable in all of Tuscany.

Spend hours (or days) wandering the ancient streets, running your fingers over some of the world’s oldest structures. Also discover “newer” buildings from the 15th century onwards and plenty medieval references.

Hunt down the old city gates (Porta di Sopra and Porta dei Merli), the famous Masso Leopoldino, the Orsini Fortress (the Museum of the Middle Ages and the Renaissance is located inside) and the Cortilone.

35 – Lap up the TLSea in Cecina

Laid-back, void of tourist crowds and situated on the coastline, Cecina is an idyllic beachside escape for lovers, families and even solo travelers craving time out by the ocean.

Thanks to its positioning in the Livorno Province, many Tuscan towns and villages boasting completely different scenery aren’t far to reach if you do want some time out in the vineyards or to explore a typical hillside town.

Kicking things off at the beach, find your classic European beach clubs along the sands of Marina di Cecina where you pay to rent umbrellas and loungers, or chill out at Spiaggia di Andalu without paying a dime. Bau Beach and Quercetano Bay are two more free beaches close by.

Leading the way to another wild and rugged oceanic terrain; amble through a pine forest with bright poppies, sea lilies and juniper bushes lining the pathway inside the Tomboli di Cecina Nature Reserve. Its nature trail walks are popular.

Traveling here with kids? Enjoy even more fun in the sun at the Acqua Village Cecina water park equipped with rides, slides and pools.

Surfing around the beaches and bays of Cecina is well-favored and local surfers flock here in the winter when the best breaks roll in.

36 – Sample some of Italy’s most famous wines at Montalcino

As pretty as a postcard or the cover of a travel magazine, Montalcino brags that typical Tuscan scenery you’ve been dreaming of.

Cypress trees grow on hilly crests, oak trees spurt in between the outskirt buildings, vineyards surround you and winding roads lead to the top of this photogenic hilltop town.

Majestic landscapes aside, if its name sounds familiar, you’re probably a wine snob and its famous Brunello di Montalcino and Rosso di Montalcino reds are imported (and savored) around the world — all cultivated in the winelands below.

Take advantage of the wine-tasting opportunities, and walking on foot through the Montalcino centro storico (historic center), stumble upon many wine bars that offer tastings and even food pairings.

Inside the old town is the Piazza del Popolo town square, Palazzo dei Priori and the surrounding Fortress of Montalcino (erected in 1361).

Whilst not in the epicenter of Montalcino, there are two awe-inspiring religious sites close by worth visiting! Founded in 1313, Abbazia di Monte Oliveto Maggiore is a stunning monastery complex and the Romanesque-style Abbey of Sant’Antimo was established in the 12th century.

• Tours & Activities in Montalcino

37 – Visit the famous Bagno Vignoni spring!

An Italian wonder; Bagno Vignoni is the only town plaza in Italy where the center of the square has no ground but is instead filled with a hot spring!

That’s right… Created and first used by the Romans, the 49-meter-long by 29-meter-wide pool is indeed a thermal spring and is the star attraction in this hilltop hamlet.

Swimming may be forbidden inside the naturally heated ancient Roman bath, however, there are free hot springs to take a healing soak around the village of Bagno Vignoni, like Parco dei Mulini.

There are also small streams running down the hillsides that flow from the main thermal pool and here you can take off your shoes and dip your feet into the sulfur-rich waters for a foot soak.

Completely car-free, stroll through the tiny alleys and passages where stonewall cafes, bars and trattorias line the sides. Crowd-pleasers are Osteria del Leone and La buca di Enea .

Perched above Val d’Orcia, it’s a great place to stop over while wine-touring the region.

38 – Relax and rejuvenate in Chianciano Terme

One more famous thermal spa town destination to know about is Chianciano Terme.

Since the early ages and Roman times, these hot springs have been utilized for their special healing properties, with waters flowing from the Sillene spring.

Around the Senese commune are numerous thermal baths, the most popular being Piscine Termali Theia (the Theia Thermal Pools).

Dip in its main Etruscan bath (high in carbon dioxide, calcium carbonate, bicarbonate and sulfates) built with some modern features like a whirlpool and jets, and there is an on-site spa here too.

Visit the Terme Sillene where they employ hydro and drinking water therapies using water from the spring to help ailments like IBS and indigestion.

Parco Acqua Santa and Parco Fucoli are two public parks with thermal springs running through them.

Other interesting things to see and explore are the Museum of the Collegiata , Castello dei Conti Manenti monastery and the Archaeological Museum of Water.

39 – Head to Italy’s famous hot springs; Bagni San Filippo

Feeling hungover from all the wine drinking going on in Tuscany? Soak your muscles, soothe your aching heads and let all the wine worries from the day before slip away inside Bagni San Filippo — an insane Instagram moment that’s for sure!

The setting of these natural hot springs and its waterfalls feels like you’re on a different planet! Plus, you can visit the famous thermal pools for free!

Positioned inside the Monte Amiata forest in Val d’Orcia, take a short 10-minute walk along a pathway leading to the natural wonder.

Arriving at Fosso Bianco (as the springs are called), marvel over the calcium-rich waters that have bundled together over water cascades to form these unique, white rock formations and pools of thermal waters — which reach temperatures between 25 and 40 degrees Celsius.

Falling into terraced pools, one of the terraces is nicknamed “White Whale” because, from certain angles, it looks like the mouth of a whale!

In the minute town (with a total population of fewer than 100 residents), there are one or two restaurants and cafes, and the hot springs can easily be accessed from the village.

40 – Appreciate religious wonders at Abbadia San Salvatore

Travel to the 7th century during a trip to Abbadia San Salvatore — a municipality centered around an abbey founded in 743.

Enshrouded by chestnut woods, the San Salvatore Abbey is one of Tuscany’s earliest monasteries, believed to have been established by Ratchis, King of the Lombards. The underground crypt is super impressive, sporting 32 columns, each with a different design.

The crypt holds extreme religious importance as it housed the oldest version of the Christian Bible (The Codex Amiatinus) for over 1,000 years!

The Italian name for the monastery is Abbazia di San Salvatore and the medieval village built around it takes its title from the abbey.

Near to the village is dormant Monte Amiata — once a volcano, the mountain became well-known toward the end of the 1890s when the mineral cinnabar (used to make mercury) was discovered in its underbelly.

Mining complexes were set up and the mineral was excavated until the 1970s. Stop by the Mining Museum Park to learn more. At the peak of Monte Amiata is the iconic Croce del Monte Amiata (appearing similar to the base structure of the Eiffel Tower).

Hiking Monte Amiata and summiting to the top, you’ll be able to investigate the cross up close.

• Tours & Activities in Abbadia San Salvatore

41 – Have fun in the sun in San Vincenzo

From snorkeling to kayaking, fishing, peddle-boating and sailing, the oceanic activities and outdoor adventures are tenfold in this idyllic seaside town along the Etruscan Coast.

The beaches are plentiful, the weather always great and it’s a destination treasured by couples and families.

Some of the best beaches in San Vincenzo are Rimigliano Beach (part of the Rimigliano Nature Reserve), Princess Beach, Spiaggia la Conchiglia and Nido Dell’Aquila Beach (also called Eagle’s Nest Beach).

At the Marina di San Vincenzo, enjoy a glass of vino from one of the cafes along the port promenade (Passeggiata del Marinaio).

Protecting its coastline from pirate attacks in its heyday, there are two tall towers that once guarded the city; Torre di San Vincenzo and Torre Vecchia di Campiglia.

For more fun, games and action, make your way to Tuscany’s biggest theme park Cavallino Matto — just 10 minutes north of San Vincenzo.

With rides and attractions designed for all ages, the family will want to spend at least half the morning here. Whizz around on rollercoasters, hit up the 4D Cinema, try not to get wet on the Corsair Slash riding water dinghies and catch one of the live shows or performances. With 18 holes to play, the Cavallino Matto Minigolf is also here.

42 – Enjoy great views and great company while horseback riding

As you travel through lush vineyards and rolling hills, you’ll have a pretty cool means of transportation: a trusty horse!

These leisurely rides are a great way to explore the Tuscan countryside at length; and with tastings for olive oil and wine along the way, you can enjoy a full experience while you settle into the saddle!

• horse riding in Tuscany

43 – Head to Cosmopolitan Beach for some snorkeling

Near the city of Tirrenia, this sparkling shoreline is the perfect place to begin your next snorkeling adventure!

Head into the balmy Tyrrhenian and admire the beauty below the surface, where plants and animals move in perfect unison.

You may never want to come back up!

• snorkeling in Tuscany

44 – Day trip to nearby islands from Piombino

Also situated in the Livorno Province on the tip of a cape overlooking the Ligurian and the Tyrrhenian Seas, make your next stop Piombino after your time in San Vincenzo (25 minutes apart via car).

Among the slew of seaside towns and villages that dot the Etruscan Coast, the port town is the last spot that makes up this coastline which starts in Livorno and ends in Piombino.

A popular day trip destination, that’s because from its port many tours and boat trips embark from here, especially ones to Elba Island (just 10 kilometers away), as well as to the Mediterranean islands of Corsica and Sardinia.

Hot tip; Don’t miss our selection of fun things to do in in Sardinia , and things to do in Corsica .

If you’re not keen on a boat trip, head to its special town square built on the edge of a cliff overlooking the ocean, known as Piazza Bovio. From its terraced lookout point, sweep up views of Elba Island.

Naturally, you’ll find some of the most delicious and freshest seafood at the restaurants around town.

45 – Go beach hunting between Follonica and Punta Ala

It’s impossible not to come across ancient ruins and structures anywhere in Italy which is why the city of Follonica stands out from the rest.

The moment you arrive you’ll immediately notice its rather modern-looking buildings and city center, so much so it’s joked that it’s “the Miami of the Maremma.” Great for shopping, eating and partying, it has a fabulous nightlife scene too.

Tick off the sightseeing first, like the 9th-century castle, Follonica and the Chiesa di S. Leopoldo di Follonica (Church of Saint Leopold) which was built in the 19th century — prime examples of its contrasting old and new buildings.

Found on the Gulf of Follonica, there are dozens of places to explore and things to do in Tuscany revolving around the Deep Blue, and in between Follonica and Punta Ala municipality, there are great beaches to scout.

Off the beaten track, Cala Civette beach is free from the hustle and bustle and great for snorkeling but takes some trekking to reach. Cala Violina is another quiet reprieve and you can also access the beach on foot, bike or horseback. Cala Martina is an awesome family beach.

Torre Mozza and Giardino Beach are two popular beaches in Follonica or swap salt for freshwater at the Hawaiian-themed Acqua Village Follonica with its Surfing Hill, Kamikaze and Anaconda water rides.

• Tours & Activities in Follonica

46 – Witness medieval towns and the ocean in one go in Castiglione della Pescaia

Buildings dripping in bright bougainvillea, the beach on your doorstep and with plenty of cobbled archways and stoney alleys to navigate your way through, Castiglione della Pescaia is absolutely breathtaking, considered one of Tuscany’s most scenic coastline towns!

Translating its name from Italian to English, it quite literally means the castle ( castiglione ) and fishing port ( pescaia ), and that’s exactly the type of vibe and makeup to expect…

Moving from the seafront up its hill, this is where the old town is situated and the medieval village is another fortified by ancient walls. Visit the castle for breathtaking ocean vistas, but the castle itself (now a private residence) is closed to the general public for inside viewing.

Outside the historic center sits Casa Rossa with access to the Riserva Naturale Diaccia Botrona where avid bird-watchers, cyclists and nature enthusiasts find sheer delight in its beauty and wildlife splendor.

Dedicate an entire day (or afternoon) to beach hopping, with loads of great options close to the town, such as West Beach (Spiaggia di Ponente), East Beach (Spiaggia di Levante), Spiaggia delle Rocchette and Roccamare beach.

47 – Visit the cathedral in Grosseto

Not every traveler vacationing in Tuscany wants to stay in the middle of the vineyards (or at least not the entire time), and if you’re a total beach babe that always needs the ocean nearby, think about making Grosseto your base during your time in Maremma (Tuscany’s main coastal area).

Despite being the capital of the province it’s not as touristy as you might think and is quite the opposite, usually devoid of major crowds.

Interestingly, the original city walls were rebuilt by the Medici family in the 14th century and you can trample past the 2.9-kilometer-long barricade on an outlined walkway.

The beating heart of the city is its Piazza Dante (also called Dante Alighieri Square) where the Cathedral of San Lorenzo is located.

Whilst this city doesn’t have as many antiquated and historic landmarks as others around, there are two great museums for a cultural fix. Pop into the Natural History Museum of Maremma (focusing on the region’s biodiversity, natural habitats and typography) and the Archaeological and Art Museum of Maremma.

Best beaches around Grosseto are Spiaggia Arenella, Spiaggia delle Cannelle, Caldane Beach and Spiaggia Rocchette.

• Tours & Activities in Grosseto

48 – Travel way back in time in preserved Sovana

Bravery outshines size in the persistent little tuff helmet known as Sovana, standing the test of time for thousands of years, prevailing through Roman conquests and managing to keep its original culture alive and strong.

Unlike many of the towns and villages that gave way to newer styles suited to empires centuries ago, the Southern Tuscan village seems to remain untouched by the “modern” world.

The epitome of a medieval commune, its past is rich in Etruscan heritage and you’ll probably want to photograph every single building you pass, all made from tuff stone.

Around the Piazza del Pretorio enjoy the boutique shops, and relax at one of the cute cafes in the square, and the Cathedral of Sovana is another one to give you goosebumps once touring inside.

Outside the city is the Città del Tufo Archaeological Park and this living outdoor museum is fascinating! Here, discover the Etruscan necropolis and check out the tombs built into the tuff.

Also in the archaeological park is the 2,500-year-old Vie Cave, and the famous Saturnia Springs are just 30 minutes away from Sovana — one of the best things to do in Tuscany!

49 – Experience different cultures in Pitigliano

Literally next door to Sovana is another volcanic rock town, and Pitigliano and its neighbor both form part of the “borghi del tufo” area in Tuscany (meaning towns carved from tuff stone).

From the Etruscans to the Romans to the Medicis, the city’s history is a fascinating one — and we haven’t even got to the 1600s yet — which plays a pivotal role in Pitigliano.

Circa the early 17th century and the Grand Duke of Tuscany at the time (Ferdinando I) designated the city as a Jewish settlement. Today, you can explore the ancient Jewish quarter dubbed “Little Jerusalem” and the Jewish Ghetto has been converted into a walking museum.

Visit the old synagogue and along Via Zuccarelli are local shop fronts selling traditional foods, for example, sfratti — this long stuffed honey walnut biscuit originates from Pitigliano.

Before the arrival of the Medicis, the influential Orsini family ruled the city and once the family residence, Palazzo Orsini is also now a living museum. There are 21 rooms/sections to plow through in the fort-palace.

50 – Get ready for endless beach days around Monte Argentario

Giving off similar vibes to Italy’s prized coastal towns like Cinque Terre, Monte Argentario is a beautiful destination to relax at for a few days if your time is limited but you still want a taste of a typical Italian Riviera.

(Useful to know: Monte Argentario is a peninsula forming part of the Grosseto Province and there are towns and villages scattered throughout. Once a separate island, the land is connected by a series of three narrow man made landforms.)

Light terracotta and soft pastel pink houses line the waterfront in Porto Santo Stefano, and the buildings behind construct into the verdant hills.

Porto Ercole is the second most popular town to visit in the region with similar landscaping but on a smaller scale.

You’ll become mesmerized quickly by the stunning beaches in the area where the water is so crystal-clear you can see straight to the bottom!

Spoiled for choice when it comes to ocean spots, there are handfuls of incredible beaches to choose from! Pinch yourself to believe the waters are really this see-through at L’Acqua Dolce beach and Il Purgatorio, and Cala Galera with its protective cove is great for families.

Chill on the soft sands of Spiaggia di Chiarone just in time for sunset hour, or head to the coastal Duna Feniglia Nature Reserve where La Feniglia beach is situated.

• Tours & Activities in Monte Argentario

51 – Adventure through Parco Regionale della Maremma

Magical woodlands, mountain ranges, wetlands, vineyards, olive groves, fruit orchards, forests, caves and coastlines — all this is possible to witness in one spot at the Maremma Regional Park (Parco Regionale della Maremma).

Since 1975, its 8,902 hectares of land (out of a massive 18,000 hectare-space) has remained a protected reserve, and the Regional Park stretches from Principina a Mare to Talamone, with the Ombrone River running through it.

Inside the park, pinewoods line the Ombrone River (which opens into the sea) and its coastline is dipped in rocky cliffs, dunes and sandy bays. Near the river mouth is where the wetlands prosper, like the Trappola marsh.

Trekking through the forests spot ancient holm oak trees or wild asparagus growing; hiking Uccellina Mountains you’ll find myrtle, strawberry bushes and lavender blooming.

Visit the Talamone Acquarium where the Sea Turtles Rescue Centre is located. There are 20 caves inside the park, for example, Grotta dello Scoglietto, Buca dell’Anselmi, Grotta dei Cenci and Pozzo del Granduca.

There are many ways to navigate your way through and you can tour the reserve on foot, by bike, on Canadian canoes (down the river), or for something extra special, ride through on horseback. Guided night tours are available as well.

52 – Walk the whole of Orbetello in a few hours

Famed for its lonely tower in the middle of a lagoon, that’s not even Orbetello’s most interesting facet… The municipality is formed on one of three strips connecting the Monte Argentario peninsula to the mainland and is situated on the middle one, with two lakes on either side of it.

These are the Laguna di Ponente to the west and the Laguna di Levante to the east, and they both form part of its larger Orbetello Lagoon, where plenty of activities revolve around the water.

In fact, the lagoon’s wetlands and surroundings have been under official protection since 1971 by the World Wildlife Federation, known as the WWF Orbetello Lagoon Oasis (Oasi WWF Naturale di Orbetello).

There are also two beaches (Feniglia and Giannella) to spend the day and with shallow waters, they are very child-friendly locales.

From the Orbettello bridge, admire the only survivor of nine Spanish windmills from the 15th century (Mulino Spagnolo) in Lake Orbetello, and check out other city sites like the “Guzman” Archaeological Museum and the town square where more of its Spanish influence is prevalent.

• Tours & Activities in Orbetello

53 – Find the tarot garden in Capalbio

In a country that’s inspired some of the greatest creatives and authors our world has ever seen; writers, poets and lyricists find yourself totally inspired when visiting whimsical Capalbio — the type of Italian destination you imagine conjured ideation for folk stories.

Undergoing numerous reigns throughout the centuries, this magical little hillside village in the Province of Grosseto has managed to retain its Medieval charm, and it’s interesting to see the varying styles of structures — hinting at the century they were constructed.

Enter the historic center through its two ancient entrance gates: Porta Senese and Porticina. From here, venture to the 15th-century La Rocca Aldobrandesca di Capalbio (known as Palazzo Collacchioni) and the Romanesque Church of San Nicola containing art of the Renaissance.

Those interested in the metaphysical — or anyone searching for unusual things to do in Tuscany — The Tarot Garden (Il Giardino dei Tarocchi) is simply magical!

This mosaic sculpture garden featuring the different decks from the fortune-telling playing gardens (which originated in the 15th century), was created by French-American sculptor Niki de Saint Phalle and took 20 years to complete.

Opening up in 1998, there are 22 mesmerizing sculptures reflecting the 22 major Arcanas.

54 – Boat trip over to the Tuscan Archipelago

Did you know that surrounding Tuscany is a set of seven islands known as the Tuscan Archipelago?

Located west of Tuscany between the Ligurian Sea and the Tyrrhenian Sea, these islands comprise Elba, Pianosa, Giglio, Capraia, Giannutri, Gorgona and Montecristo.

Elba is the largest of the isles and can be spotted from many a hilltop in Tuscany. It also happens to be the most popular and is frequently busy. It’s notorious in the history books for shielding the infamous Emperor, Napoleon during his exile from France in 1814.

Closest to Elba is Pianosa and its bays are exquisite! A former prison, the island is deserted but day trips are available for explorers.

Stay overnight on romantic Giglio (the second-largest island of the Tuscan Archipelago) or on its third-biggest, pretty Capraia. The waters around both are sparkling see-through and favored for snorkeling and boat trips!

Catch a ride from Giglio to Giannutri, loved by scuba divers, and Gorgona (the smallest of the islands) is known to have the best wildlife.

Before you visit the mysterious Isle of Montecristo you’ll first need permission. Completely different from the others, if flying over it in a plane it looks like a giant chunk of granite (which most of the terrain is made up of) lodged in the middle of the ocean.

The islands are easily accessible from various towns/ports around Tuscany.

How to get to Tuscany?

Tuscany’s major airport is located in the capital city of Firenze, and for travelers flying either international or domestic, you’ll fly into Florence Airport, Peretola.

Skip the hassles of trying to speak Italian to communicate with taxis where you want to go, whether it’s the Tuscan countryside or its coastline, and pre-organize airport transfers for your day of arrival in Tuscany.

When you land, have your private driver waiting for you holding a placard with your name on it — fancy right? — and be whisked away in comfort and style to your pre-booked destination.

Where to stay in Tuscany?

It doesn’t really matter where you stay in Tuscany, because everything around you is gorgeous. Stay in the middle of the vineyards, a hilltop town or on the coastline in centuries-old villas, farmhouses or hotels.

Located in the famous hot spring town, Saturnia, Terme di Saturnia Natural Spa & Golf Resort has its own private thermal baths! Plus, it’s done up to the nines in luxury.

Walking distance to many of Firzenze’s must-see sites, Palazzo Niccolini al Duomo is a stunning spot with all the old-school Florentine feels. Couples looking for a stay in Chianti? Palazzo Leopoldo Dimora Storica & Spa is a 4-star hotel in Radda, or feel like royalty at Hotel Villa Sermolli .

Agriturismo in Tuscany refers to its traditional (gorgeous) farmhouses among the vineyards and mountains. Fattoria Pratale, Castello La Leccia, Tenuta Croce di Bibbiano and L’Andana Tenuta la Badiola are amazing!

• best hotels in Tuscany

Visiting Tuscany on a budget?

If Tuscany isn’t the only destination on your Italian itinerary, save a few extra bucks where you can, like with free walking tours .

From Florence, learn of the city’s influential Medici family and facts and history about the Renaissance during two-hour Medici and Art tours, or investigate iconic monuments and landmarks during classic walking tours lasting 1.5 to 2.5 hours.

See sites like the Cathedral of Santa Maria del Fiore, Piazza della Repubblica, the Uffizi Gallery, the Baptistery of San Giovanni and plenty more!

Alternatively, opt for the road less traveled and amble your way into the ‘Dark Side of Florence, Mysteries & Legends tour.

Where to go next?

If you’re the type of traveler that enjoys sightseeing more than one place, there are many other great places to visit in Italy .

Splashed across Instagram feeds and one of Italy’s most famous cities to the travelworld, Cinque Terre is iconic. Picture colorful houses sitting in between sea cliffs overlooking the ocean… Plenty of villages to explore, the top five are Riomaggiore, Corniglia, Monterosso, Manarola and Vernazza.

Or, head up north to Bologna in the Emilia-Romagna region (roughly 1.5 hours away). This historic city isn’t just famous for its food, but it’s filled with history too, including the UNESCO-listed Porticoes of Bologna .

It would be silly to travel to Italia and not visit historic Rome , even if it’s just for two days. From the Vatican City to the art to the museums to the food, this is one Italian city you simply cannot miss.

Depending on your location in Tuscany, Rome is 2.5 to three hours away.

Final thoughts

Honeymooners, art-appreciators, wine-lovers and families after an authentic Italian vacation, this part of the country is just perfect.

If you’ve traveled to Central Italy before, what were some of your favorite things to do in Tuscany or your most memorable moments? Wine tours? Hot air balloon rides? Bathing in accent thermal baths? Share with us in the comments!

As always, happy travels!

31 Hidden Gems in Tuscany – How to Get Off the Beaten Path

May 28, 2023

Explore these hidden gems in Tuscany and leave the crowds behind. Find secret spots, alternative places and get off the beaten path in Tuscany with this inside guide.

Find Unusual Things to do in Tuscany​​​​​ with these Hidden Gems

Tuscany has plenty upon plenty of things to do, that’s for sure. With no fewer than seven UNESCO World Heritage Sites, the claim as the birthplace of the Italian Renaissance, the Leaning Tower of Pisa and more, it’s no surprise that Tuscany remains one of the most popular places to visit in Italy, if not the world.

And yet. Stunning though these places are, it does mean that some of the off the beaten track things do get overlooked. Experiences that would top the list in lesser-endowed places fall through the travel guidebook cracks in luscious Toscana.

Well, not any more!

Behold, dear readers, let me clue you in to off the beaten path things to do in this part of Italy with these hidden gems in Tuscany.

Recommended reading: unusual things to do in Italy

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Tuscany Off the Beaten Path

Visit the Vespa Museum

The Vespa museum in Pontedera, Tuscany, welcomes you not with racy Vespas and photos of celebrities, nor dashing ad campaigns. Those wait inside. Instead there’s a memorial and a polished aerobatic trainer plane, monuments to the man who began his career in aeronautical engineering but who achieved fame with a much smaller machine: the Vespa. It’s one of the best hidden gems in Tuscany.

On the one hand there’s the breathless icon, the vision of beautiful Italian limbs perched upon beautiful Italian design, zipping past fountains, ochre walls and cafes practically swaying with romantic intrigue. On the other, there’s a bald man in a shirt and tie. The man who designed the thing.

That man was Corradino d’Ascanio.

Inventing the Vespa

Piaggio hired d’Ascanio, they both got to work and after a few shiny prototypes, the Vespa was born. Its unique design had gears on the handlebars, a single metal chassis and an easy way for riders to rest their feet on the platform instead of straddling an unwieldy mechanical beast.

Splash guards even protected those tailored Italian suits.

Either from the Vespa’s narrow waist or from the buzzing of the engine, the motorbike reminded both men of a wasp. This was handy, since Vespa in English means wasp.

Fame and Hollywood followed, surpassed only by a visit from the British Blue Peter team.* The Vespa became both a legend and an art form and the museum in Pontedera celebrates it well.

Yet the words on the plaque by the exit are the ones that stay with me still:

“Corradino d’Ascanio, 1891 – 1981

A man of science and extraordinary imagination and creativity.

The book of his life tells the story of aviation, the helicopter and the Vespa.”

The museum also shows glamorous photos of a woman with long hair clasping the man of her dreams as they speed through the Tuscan countryside.

Behind every sexy invention, you’ll find an engineer.

Take An Authentic Cooking Lesson in Tuscany

“This is the classic ragù that my grandmother taught me: a delicious, versatile sauce that can be used in many ways. Added to lasagne, any type of pasta, served with meatballs…” Lella from Cuoche in Vacanza

It’s no secret that Italians like their food. And one of the best hidden gems in Tuscany is having a secret cooking lesson so that you can bring the flavours of the region back home.

I loved the in house cooking course with Cuoche in Vacanza. They come to your self catered accommodation or villa and teach you all the tricks of the trade.

Find the recipe for the real ragu and the details for the cooking lesson over here. 

Wander the Charterhouse of Calci

In unmarked graves, the Charterhouse monks of Calci used death to extend their earthly vows of silence into eternity.

While the brothers ran the pharmacy, the fathers lived reclusive lives, speaking only once a year and passing food between walled tunnels to avoid the temptation for a chat.

Yet despite this severity, austerity never really caught on.

The Charterhouse notches up an impressive 1500 rooms, plus a view of the leaning tower of Pisa on that infamous clear day. Living quarters come with private orchards, while cloisters overlook fountains and a gated panorama of Tuscany at its best.

In fact, it’s this very richness that’s the real curse in this part of Tuscany. With the splendours of Florence and Pisa nearby, little attention remains for buildings that would otherwise be protected, promoted and thriving.

Like the others, the Charterhouse is struggling. The last monks left in the 1970s, leaving the cloisters crumbling behind them.

Part of me wonders whether this is how things need to be. That it’s impossible to restore and remember everything and that in trying to do so we risk losing today’s resources.

But then another part recognises this as one of Tuscany’s hidden gems. And hopes that it survives.

Find a laughing ghost

Agustino Agustini greets guestsin the hallway of Villa di Corliano, a house, no make that a mansion, complete with a driveway that sweeps through the grounds like a flourish from a period drama. Florentine eagles flit across the vault, while whispers of ghosts hide behind chandeliers.

You can stay here, in this lovingly restored unusual piece of history . But you have to be able to handle the ghost. 

Go Bird-watching at Massaciuccoli

Bring your binoculars and drink in the soothing silence of sunset. Look out for kingfishers and ducks amid the swaying reeds above and crayfish and eels below. Find out more about walking in Massaciuccoli here.

Take a Road Trip Through Tuscany

Embrace the freedom of the wide open road and those lines and lines of cypress trees by finding your own way through Tuscany. That way, you can hit the main sights of Florence or Pisa and then take in these unusual spots plus discover a few more surprises of your own.

Recommended – Road Trip Essentials: How to plan the perfect road trip anywhere in the world.

Visit an Agroturismo Farm

Indulge in homemade jams, honey, extra virgin olive oil and a meal made from vegetables grown in the very same garden. All while taking in views of the Serchio River. Spazzamento calls this agriturismo. I call it simple pleasure.

Find out more about the Agriturismo Spazzamento here.

Meet the Gloom of the Nicosia Monastery

Beneath the arches, a cloaked man walks through the shadows, his head bent, his hands supporting an open book. I can hear my footsteps, distorted through the darkness by the basement’s wet gravel, a hesitant chord to the beat of dripping water.

Upstairs, in the clouded daylight, it’s easier to see the wooden planks covering the windows and the words that scream “take my blood.” It’s also easier to see the table decked with homemade olive oil, bread and wine.

This is the Nicosia Monastery, a place that chalked up nearly 800 years of active service before the last few monks hung up their cassocks in the 1970s and the vandals moved in. Among the ripped plaster and violent graffiti, a neatened orange grove provides fragrance and a sense of peace.

It’s being painstakingly restored by the Nicosia Nostra, a volunteer organisation founded in 2004 from people in the neighbourhood who wante to save the place. They host outdoor concerts in summer, construct nativities in winter, and spend the rest of the year lurking in basements to scare the bejesus out of visiting writers.

Talk about Tuscany’s hidden gems.

FAQs about Tuscany Hidden Gems

You asked, I answered! Here’s more about Tuscany off the beaten track.

What is Tuscany known for?

Tuscany is known for rolling hills, olive groves, medieval towns and great food. The region has a huge artistic and historic legacy, as both the birthplace of the Renaissance and the home of the modern Italian language. It’s also a popular holiday spot, with cities like Florence, Siena, Lucca, Pisa, San Gimignano, Montepulciano and more.

What are some non-touristy things to do in Tuscany?

Beyond the secret spots in Tuscany mentioned higher up, some non touristy things to do in Tuscany include the following:

• Catching the sunset views at Pitigliano.
• The Saturnia Hot Springs.
• The natural thermal baths at Bagni San Filippo.
• Porto Santo Stefano – a beautiful coastal town.
• Giglio Island – a gorgeous spot within the Toscano National Park.
• Lajatico – the hometown of one Andrea Bocelli.
• Val D’Orcia for those iconic countryside views.
• San Gimignano – popular hill town with towers to climb.

Where in Tuscany has the most beautiful rolling hills?

The region of Val D’Orcia is probably the most famous part of Tuscany, with those rolling hills and upright trees.

Where to stay in Tuscany off the beaten path?

You will find so many gorgeous places to stay in Tuscany off the beaten path. I’d highly recommend the places recommended in this article on hidden gems in Tuscany. Namely: Villa Corliano.

What is the most beautiful part of Tuscany?

Well, beauty is in the eye of the beholder, of course. But it’s hard to beat the rolling hills of Val D’Orcia.

Read more about Italy with these travel tips

• The world knows Rimini for its beaches but what about Rimini Old Town?
• The landmarks in Italy that everyone should see at least once
• 21 Unusual Things to do in Rome That Aren’t Just Weird
• How to Make a Ragu Your Italian Nonna Would be Proud Of
• Your Perfect Amalfi Coast Itinerary
• Chiavenna: The Place That Makes Caves Glamorous
• Yes, You Can Still Find Secret Spots in Venice
• 7 Unusual Things to do in Italy to Fall in Love All Over Again
• With These Italian Souvenirs, You’ll Always Remember Italy
• The Best Things to do in Umbria, Tuscany’s Neighbour
• Trieste Food Stands Out From the Rest of Italy

2 thoughts on “31 Hidden Gems in Tuscany – How to Get Off the Beaten Path”

Ohh I love this post! I love how you don’t travel in the typical touristy way. I recently moved to Tuscany, so this blog post is perfect for my sunday adventure inspiration. Thank you xx

https://shannicealice.wordpress.com

Ah, what a beautiful part of the world to move to! So many adventures await! Glad you found this helpful – and wishing you all the best in your new home!

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The Weird and Wonderful: 14 Unusual Things To Do in Tuscany

1. galileo’s middle finger, florence, 2. officina profumo-farmaceutica di santa maria novella, florence, 3. perseus with the head of medusa, florence, 4. isola santa, apuan alps, 5. taste truffles, san miniato, 6. museo piaggio, pisa.

Difficult as it may be, you’re going to steer clear of the Piazza dei Miracoli. You’re not here to see the Leaning Tower. No, you’re looking for unusual things to do in Tuscany and Pisa’s here to sort you out.  They are perhaps the most popular mode of transport in Italy. You see them everywhere. People shoot up and down avenues and tear around narrow, windy side streets atop them. The Vespa, Piaggio’s racy, two-wheeled scooter is so much a part of Italian culture and identity, they should put it on the flag.

For a complete look into the history of the company, head 25 kilometers south of Pisa and enjoy their museum. Housed in a 3000 square meter former tool shop, you can now learn everything you’ve ever wanted to know about the company. From its start in 1921 all the way through to its production of aircraft, destruction during WWII and the eventual development and restyling of their famed Vespa.

7. The Charterhouse of Calci, Calci

8. san rossore nature park, pisa & luca, 9. visit carrara marble quarries, carrara, 10. saint catherine’s severed head, siena, 11. montesiepi chapel’s “sword in the stone,” siena, 12. parco dei mulini, siena, 13. vie cave, siena province, 14. horse riding in maremma.

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15 Unusual things to do in Tuscany

Are you looking for some unusual things to do in Tuscany ? You’ve come to the right place. Not everybody is content with the same-old holiday destinations and popular sights, so we’ve gone far and wide in search of the most unique and unusual things to during your Tuscany trip . Some are different, others are plain weird, and all will show you a side of Tuscany you weren’t expecting. This is a list for the curious travel who would like to get off the beaten track. And discover a whole new side of this beautiful region .

15 Unusual Things to do in Tuscany

1. discover tuscany’s very own sword in the stone.

You wouldn’t expect to find a sword in the stone in Tuscany . But trust us, it’s there. There are strong Arthurian influences in the legend of Tuscan-born Galgano Guidotti . Galgano was a dissolute and ruthless knight who hurled his sword into a rock when he decided to renounce violence and embrace a pious life. He was made a saint and a chapel was built in his honour. Today inside the small chapel Rotonda di Montesiepi , you can see the ancient sword still stuck in the very spot where he put it. Medieval vibes, mystery and spirituality in one.

2. Dare to walk the Devil’s Bridge

If you drive a few kilometres north of Lucca , on the way to the verdant Garfagnana , you’ll encounter a singular bridge with a dark story to tell. It’s the Ponte della Maddalena , and dates back to the Middle Ages. A beguiling sight, it’s often known by another, more chilling name – The Devil’s Bridge .

Legend goes that the architect who built it, fearing he wouldn’t be able to finish his job on time, asked Lucifer for help , offering him the soul of the first man to cross the bridge in return. But when morning came, and the bridge duly finished, he tricked the devil into sending a pig to cross it. So saving his soul. Walking across this scenic and storied bridge is definitely one of the more unusual things to do in Tuscany .

3. Uncover the secrets of Palazzo Vecchio in Florence

Would you like to discover the secrets of the Medici family inside one of Florence’s most handsome palaces, the Palazzo Vecchio? This imposing edifice is where the rulers of the city, the Medici, used to live. if you join the Secret Passage Tour of Palazzo Vecchio you will not only appreciate the beauty of its interior, but also learn a few intriguing pieces of Florentine history. Fun, original , interesting. Not to be missed!

4. Explore Little Jerusalem in Pitigliano

Pitigliano is an enchanting hilltop town in southern Tuscany . It’s here you’ll find one of the most unusual sights in the region. “Little Jerusalem” is an ancient Jewish quarter in the town, dating back to the 16th century. The synagogue, and some rooms excavated in the tufa rock , can be visited to learn the evocative and moving history of this Jewish community in central Italy.

5. Saint Catherine’s relics in Siena

If you’re in the mood for something slightly macabre , visit the San Domenico Church in Siena . Here you’ll find the mummified, severed head of Saint Catherine , one of the patron saints of Italy. The young Caterina used to pray and have visions in this church, which has become a place where her spirit rests . Gruesome relic, or the perfect representation of the more visceral side of Medieval spirituality? You be the judge.

6. Get inspired by the Tarot Garden in Capalbio

On a more joyful note, head to the Tarot Garden near Capalbio in the Maremma . Right at the southern tip of Tuscany there’s a Gaudi-inspired place created by French artist Niki de saint Phalle . The garden was opened to the public in 1998. The sculptures that adorn it are made of multicoloured glass and other materials, and create a little world of fantasy and Tarot-inspired symbolism , where nature and art mix in an inspiring combination.

7. Visit a marble cave in the Apuan Alps

Get inside the belly of Tuscany. Visiting one of Tuscany’s marble caves is a way to really appreciate something that has made this region famous and unique: white marble. Michelangelo used to come up into the Apuan Alps in search of the perfect block of marble for his creations, so you could say his statue of David was born right here. This mountains have also provided marble for countless edifices and monuments all around Tuscany and Italy. Explore one of the caves in the Apuan Alps with an expert guide , breathe in the fine marble dust that fills the air, and you’ll begin to appreciate all the beauty and hardship of life in this part of the world.

=> Discover the town of Colonnata on the Apuan Alps

8. Riding a Vespa around the Tuscan hills

Rent a Vespa and get set for an adventurous ride along Tuscany’s curvy road . Snake through olive groves and beautifully combed vineyards, enjoy the views and the thrill at every bend . But be careful, Italian driving can be a bit unpredictable 😉

Did you know that the iconic Vespa motorbike was born in Tuscany? The first Vespa was produced in Pontedera, where there’s a museum dedicated to the Vespa, a fun way to spend an afternoon.

9. Pay a visit to the La Verna Hermitage

If you’re looking for peace and quiet on your holidays – and you’d like to explore an area of Tuscany known only by the most savvy traveller – head to the Casentino . And book a night at La Verna Hermitage , the Franciscan monastery that welcomes pilgrims from all over the world. People come here for silence, prayer, and to hike in the beautiful forest surrounding this ancient religious site.

10. Driving aournd the Accona Desert in the Crete Senesi

In Tuscany , a region famous for its verdant countryside, you probably won’t expect to find a desert . But right at the heart of the Crete Senesi , south of Siena, there’s a place known as the Accona Desert . It’s a hilly eroded area devoid of vegetation, more properly called ‘badlands’. A lunar landscape that looks strangely suggestive and otherwordly .

=> Badlands are a type of dry terrain where soft rocks and clay-rich soil have been extentively eroded, creating formations like the Tuscan ‘biancane’ -> bianco means ‘white’ in Italian, from the colour of the soil . ( Wikipedia )

=> See the Best of the Crete Senesi .

11. Take part in a Medieval Festival

The Middle Ages are still very much alive all around Tuscany. You can see it in the tower houses, the historic centres, churches and museums. But if you want to really experience the Medieval atmosphere , the best way is to take part in one of Tuscany’s many Medieval festivals . You could get a ticket for the Saracino Joust in Arezzo, where knights on horses compete, or visit the Monteriggioni or Volterra Festival. => See 3 Great Medieval Festivals in Tuscany .

12. Sleep with a ghost

What’s more exciting than sleeping in a haunted castle during your stay in Tuscany? If you’re up for this kind of things, look no further. Book a night at the Fosdinovo Malaspina castle in northern Tuscany . It is believed to be haunted by the phantom of Bianca , the young and rebellious daughter of the Signore. Only the intrepid traveller ventures to this remote corner of Tuscany, the Lunigiana . But there’s no better place to escape the multitudes, and the ordinary.

13. Meet the Prehistoric “stele” statues in Lunigiana

Let’s stay in northern Tuscany, and visit a truly unusual museum: the Museo Statue Stele in Pontremoli . The Stele are anthropomorphic statues sculpted in local sandstone by the peoples who lived in this area between the IV and the I millennium B.C. If you like history, or in this case prehistory , this is your place. Leave modernity aside and immerse yourself in the enigma that this enigmatic ancient sculptures still are today.

14. Water sport in Maremma

When Summer comes, the Italian coasts fill with people and excitement . And in Tuscany, the best beaches to enjoy it all is the Maremma . This is also a good destination if you like water sports: locations like Castiglione della Pescaia and Mount Argentario offer a range of activities like rafting, sailing, kite or wind surfing.

=> Discover 8 Reason to fall in love with the Maremma

15. Truffle hunting in San Miniato

Tuscany is one of Italy’s hot spots when it comes to truffles . San Miniato is a small hilltop town, with a lovely historic centre and a few excellent restaurants, that every November hosts a renowned Truffe Festival . Here you can also book a guided Truffle Hunt with a local expert and his dog , for a fun experience that will introduce you to the mouth-watering world of truffles.

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25 Unforgettable Things to Do in Tuscany

Home » Blog » Europe » Italy » 25 Unforgettable Things to Do in Tuscany

If you’re planning a trip to Italy’s famous region, we’ve rounded up all the essential things to do in Tuscany, including where to eat and where to stay. Plus we’ve included some helpful tips for traveling to this picturesque and historic country. 

As the second most visited region in Italy, second only to Veneto (where Venice resides), there is a seemingly endless list of things to do in Tuscany.

While most famously known for its rolling hills and award-winning wines, the region’s highlights are chock full of Renaissance art, UNESCO World Heritage Sites, outstanding cuisine, pristine nature, and some of the most significant architectural marvels in the world.

With so much to consider when planning your trip to Tuscany, it can be overwhelming. Especially since you won’t be able to see and do everything on your first visit.

This guide to the must-see things to do in Tuscany will help you narrow down your search and fill your time with the absolute best activities. 

In addition to all the sites and attractions, we’ve included tips for where to stay, how to get there, how to get around, and when to visit that will render useful for your trip planning. 

Tuscany Travel Guide

For more tips and advice for planning your trip to Tuscany, Italy, jump to the following sections (or just keep scrolling to see it all!).

• How many days do you need
• Best time to visit
• How to get there
• How to get around
• Tips for visiting
• Where to stay
• What to pack

Top things to do in Tuscany

If you’re looking for the very best things to do in Tuscany, here are our top recommendations: 

• Hang out in Florence
• Tour the countryside on a vintage vespa
• Go wine tasting
• Stay at an agriturismo
• Take an Italian cooking class
• Road trip through Val d’Orcia

Keep reading for more detailed information on each of these things and more ideas of fun things to do in Tuscany. 

1. Hang out in Florence

As the capital of Tuscany, and the birthplace of the Renaissance , Florence is a massive, living museum in the heart of the region. 

A few days in the city is a right of passage for anyone exploring Tuscany. 

Travelers flock here for a chance to visit some of the world’s most famous art galleries, admire the architectural marvels, and get lost in its maze of narrow streets.

Top things to do in Florence

We have a complete guide for things to do in Florence , but if you’re looking for some of the highlights, here are our top recommendations. 

• Walk along the Ponte Vecchio. The oldest bridge in Europe and the pulse of Florence.
• Climb Giotto’s Bell Tower. The top of this Gothic masterpiece offers expansive views over the city.
• Watch the sunset from Piazzale Michelangelo. Watch the sun fall behind Florence and its backdrop of Tuscan hills.
• Marvel at Michelangelo’s The David sculpture. Arguably one of the most famous pieces of art in the world inside the Accademia Gallery.
• Go on a food tour and discover Tuscan specialties like crostini toscani, Bistecca alla fiorentina, and pecorino cheese.
• Gaze at Il Duomo from every angle. The largest masonry dome in the world is painted with iconic murals.
• Check out the Galleria de Uffizi. Widely acclaimed as the best art gallery in the world with works by Michaelangelo, Da Vinci, Botticelli, and Giotto.

Want to save time and energy on planning?

We’ve spent a collective 6+ months living in and traveling around Italy, and we’ve been able to explore a lot of what this country has to offer!

We’ve compiled our experience to create a classic Italy itinerary that hits the top destinations for first time visitors. Our itinerary is spread out over 10 days and includes the highlights of Rome, Cinque Terre, Florence and Venice .

We’ll send you our complete 10-day itinerary, filled with tips and advice. Just click below to get your  classic Italy itinerary  today!

2. Ride a vintage Vespa through the Tuscan countryside

Whizzing past the vineyards and rolling hills of Tuscany is one of the best ways to take in the region’s rustic and raw beauty.

On this Tuscan Countryside Tour , you’ll leave Florence in a fleet of vintage Vespas en route to jaw-dropping castles, villas, vineyards, and olive groves.  

Stop for a glass of Chianti wine,Tuscany’s best prosciutto, and cheese overlooking a magnificent view from the terrace before cruising back to the city. 

What you need to know:

• Hours: 5 hours
• Price: $162.96 USD / person

What guests are saying

“To say that we had an amazing time on this excursion is an understatement! […] We stopped a few times to take photos of the Tuscan countryside and Firenze while Gabriel shared a lot of interesting information along the way. […] It honestly felt like a dream and that we had an authentic Italian experience…” – GetYourGuide Traveler (May 2023)

Prefer 4 wheels?

This Classic Car Experience takes you around the hills surrounding Pisa, Florence, and Siena. 

Put your manual driving skills to good use, or have your own driver chauffeur you around in a vintage Fiat Spider, Alfa Romeo, MG B, VW Beetle convertible, or other iconic ride.

• Hours: 3.5 hours
• Price: $217 USD / person
• Location  

“This experience is AMAZING! […] Lorenzo was an absolutely stellar guide[…]  We had a great time and even stopped for a little aperitivo in the town. Overall, this was a great time for anyone looking to have a little fun and see some quiet Tuscan towns, great views of all the wineries, and enjoy some long drives in classic cars!” -Nina, United States (May 2022)

3. Go wine tasting

Tuscan wines are respected for their prestigious pours all over the world. 

If you’ve ever indulged in a glass or two back home, there’s a good chance it’s been of the variety. While you can sip on them at wine bars around the region, nothing compares to getting it straight from the source in one of the best wine regions in Italy.

From small producers to artisan vineyards, there are a variety of different areas to taste the famous love affair with exceptional Tuscan wines. 

Different wine regions in Tuscany

The regions that are most synonymous with the Tuscan wines are Chianti , Montepulciano , and Montalcino .

Chianti is arguably the most famous out of all the wine regions in Tuscany. It’s known for its world-class wines, particularly in the Sangiovese variety. It’s close to Florence and makes for a convenient day trip. 

Montepulciano and Montalcino are situated in the UNESCO-tagged Val d’Orcia, so they have more of the classic Italian vineyard experience with the expansive views over the region. The two are only separated by the town of Pienza, so they’re commonly visited together. 

Wine tasting tours in Tuscany

To visit the wineries in Tuscany you can self-drive with a designated driver, hire a private driver, or book a tour. 

By far, a tour is the best way to do this because you don’t have to deal with the logistics of getting around and it’s much cheaper than hiring a driver, which can cost upwards of $600 USD!

These are some top-notch tours around the region:

• Small group wine tasting tour from Florence : Visit 2 acclaimed wineries in the Chianti region. Sample 6 different wines with local olive oils, cheeses, salami, and bruschetta over breathtaking views.
• Unforgettable Tuscan wine tour : Gather in the Chianti region for an all-encompassing experience of wine making. Venture to a winemaking villa and two family-run vineyards to learn about the production processes, tour the cellars, and taste their wines with Tuscan specials. Conclude the tour with aperitivo in the heart of Chianti. 
• 3 wineries Tuscan wine tour : Dotted in the Chianti shire, partake in tastings at 3 family boutique wineries. Learn how to properly taste wine, how to distinguish types, and learn about the processes from real experts.
• Montepulciano wine tasting and cellar tour : A tour of this medieval wine cellar offers 5 DOC and DOCG wines paired with bruschetta and olive oil. Their ancient soil and quality aged wood produce their famous red wine.
• Guided e-Bike and wine tour from Lucca : Cruise around Lucca’s historic highlights before peddling to the countryside for a tasting. Tour the cellar then sample wines with local bruschetta, meat, cheese, and olive oil.

4. Stay at an agriturismo

A distinct accommodation signature of Tuscany, Umbria, and Sicily, is an agriturismo, a working farmhouse that has been turned into a guesthouse .

Not to be mixed into a regular ol’ farmstay, agriturismos are distinct. 

They receive more money through agricultural practices than renting rooms, and you must be served local products from the farm during your stay like olive, oil, wine, and fruit. Any stay that doesn’t meet those requirements is considered a farm stay or B&B.

Consider these agriturismos for your dreamy stay in the Tuscan countryside:

Budget option: Agriturismo Pompilia

Sandwiched between Florence and Pisa, this budget-friendly stay is surrounded by olive groves and vineyards in the hills of Volterra. They have a saltwater pool, restaurant nearby serving authentic dishes, an onsite bar, bookable activities, and a spectacular location. Each apartment comes with a kitchen, private balcony, free Wifi, and expansive views. 

Mid-range option: Agriturismo Baccoleno

A paradise near Asciano, you may never want to leave this hillside estate surrounded by rolling hills and cyprus trees. Relax in the hot tub, indoor pool, or on the patio with a garden view. Each apartment comes with a small kitchenette, dishwasher, and washing machine, making you feel right at home. The wine town of Montepulciano is only 40-minutes away and Siena less than an hour.

Mid-range option: Agriturismo Il Casalino

Situated between two wine towns south of Pienza, and right in the middle of the Val d’Orcia, the location of this stay is unmatched. This immaculately restored 19th-century farmhouse has free Wifi throughout, unparalleled views over the hills, bookable tours, bike rentals, and plenty of outdoor spaces for relaxation.

Splurge option: Agriturismo San Tommaso

Cradled by mountain views and the quintessential Tuscan backdrop, this stay is outfitted with an outdoor pool, hot tub, balconies in each apartment, kitchen, hiking trails nearby, and onsite bar. Authentic cuisine is whipped up onsite and nearby villages are just a short drive away.

Splurge option: Agriturismo Le Gallozzole

Just south of Florence, this antique working farm is updated yet still maintains its historic charm in the Tuscan wine country. During your stay, you’ll have access to the outdoor pool, exceptional onsite restaurant, daily pastries, and the properties olive oil and wine. Each apartment has all the amenities and views you need for a memorable experience.

Important Note: They often have a minimum stay so keep that in mind as you search for the perfect one and plan your visit.

5. Take an Italian cooking class

From the cities to the countrysides of Tuscany, chefs and nonnas alike offer a variety of cooking classes where you can perfect the art of Italian cooking.

Cook with Cristiana and Mamma Nora

Learn the secrets of homemade pasta and tiramisu just outside Siena during Cristiana and Momma Nora’s Cooking Class . 

You’ll cook using all their organic products like farm fresh eggs, ancient Tuscan grains, and seasonal vegetables. Create handmade pasta, a complimentary sauce, and the most famous Italian dessert in a warm and loving atmosphere.

• Hours: 5.5 hours
• Price: $119 USD / person

I took this cooking class on my last trip to Tuscany with my mom and we loved it!! It was one of the highlights of our entire trip to Italy! Take a look at the back-to-back reviews my mom and I left for Cristiana…

Luca & Lorenzo, cooking in Chianti hills

In the woodlands of the Chianti Hills, you’ll cook homemade pasta, sauce, and a traditional Italian dessert during Luca & Lorenzo’s Cooking Class . 

Fueled with wine, snacks, and an aperitivo, you’ll use the freshest herbs, olive oil, and other ingredients to perfect your dishes. The chefs will tell stories and give expert instruction as you cook and gaze out at stunning vineyards.

• Hours: 6 hours
• Price: $153 USD / person

“This experience was everything we imagined and more[…] From the moment we met at the train station, we felt like they treated everyone as if we were all family. The pasta and tiramisu lessons were outstanding, especially for an Italian like me trying to learn how it’s all done!…” – Nicholas (May 2023)

Pizza and Gelato Class at a Tuscan Farmhouse

For the most indulgent experience cooking in Tuscany, join this Pizza and Gelato Class hosted inside a beautiful Tuscan farmhouse. 

A professional chef will take you through the process of kneading and molding dough and choosing the perfect toppings picked directly from the estate’s garden. 

After devouring your handmade, wood-fired pizza , learn the special techniques to make creamy gelato as a dessert.

• Price: $192.29 USD / person

“This has been the highlight of our trip to Florence! The farm was beautiful, the teachers were informative and entertaining, and the process from start to finish was great all around. It was a hit with kids and adults alike who love gelato (who doesn’t?)…” -‘The Family with a Girl like the Air’ (April 2023)

6. Road trip through the Val d’Orcia

An area that seems to have been painted by a Renaissance artist themself, Val d’Orcia is a UNESCO protected valley where verdant rolling hills are decorated with cyprus trees and poetic villages .

As the landscape that made Tuscany famous, every turn on a road trip through here will have you picking your jaw up off the floorboard, but here are some of the most famous stops:

• Vitaleta Chapel : Secluded and quaint chapel tucked between two cyprus trees.
• Pienza : Visit the valley below town after exploring the “ideal city”.
• Montalcino & Montepulciano : Medieval hilltop villages surrounded by vineyards.
• San Quirico : For the trademark cyprus trees.
• Abbazia di Monte Oliveto Maggiore : A beautiful abbey nestled in the trees and rolling hills.
• Bagno Vignoni hot springs : Historic natural hot springs that’ll have you bathing like the Romans did. 

7. Soak in a natural hot spring

All across Tuscany you can dip your toe into natural soaking pools of all shapes and sizes.

The most famous hot spring in Tuscany, and in all of Italy really, is Saturnia Hot Spring . Its milky blue cascading pools gained their fame on Instagram, and rightfully so!

But if you want to explore other hot springs in the region, there are many in Tuscany worth checking out: 

• Bagni di San Filippo : These hot pools appear to have been created by melted snow.
• Terme di Petriolo : This well-known hot spring is famed for its surrounding nature and salt-rich waters.
• Bagno Vignoni : Some of the hottest springs in Tuscany. The one in the piazza is closed for visitors, so you need to go to the Parco dei Mulini just below town to soak.
• San Casciano dei Bagni : Roman-age pools in the town’s main square.

8. Float in a hot air balloon over Tuscany

A Balloon Flight Over Tuscany takes you nearly 2,000 feet into the air and uses wind and fire to glide you across the region’s magnificent hills and vineyards.  

As you float, gaze out upon the main highlight, San Casciano in Val di Pesa, filled with castles and countryside scenery. At the end, you’ll celebrate wherever the breeze took you with a glass of champagne and breakfast.

• Hours: 3 hours
• Price: $293.61 USD / person

“What an amazing experience flying over Tuscany in October over the sunrise. It exceeded all of my expectations, and I would do it again in another location with these guys. Everything was very well planned with a wine and charcuterie picnic to celebrate at the end.” – GetYourGuide Traveler, United States (October 2022)

9. Test your skills at truffle hunting

On the grounds of a private 12th-century winery settled in the rolling Chianti Hills, you can join a Truffle Hunting Tour to search for rare fungi.

You’ll explore the family estate with the winemaker before venturing into the woods alongside three friendly truffle pups to begin your hunt. After bringing back a generous haul, conclude the day with a home cooked meal and Chianti wine.

• Price: $173 USD / person

“Trust the 5 star reviews. This experience was, without a doubt, the best of our entire trip! The truffle pups (3 pups!) AND the hosts were so friendly and fun! It’s an experience unlike anything else you’ll do in Italy…” – Justin, United States (May 2023)

10. Snap a cheesy photo in front of the leaning tower of Pisa

Holding it up or pushing it over, a photo with Pisa’s famous tower is nearly a right of passage when in the region as it’s one of the most popular things to do in Tuscany..

It began as an architectural mistake nearly 800 years ago, and today is one of the most famous landmarks in Italy . Beyond the tower, though, Pisa is worthy of a visit all on its own.

Psst! We have a complete guide on how to get to Pisa from Florence that breaks down all of your transportation options and covers all the details you need to know.

Other things to do in Pisa

We have a complete guide for things to do in Pisa , but if you’re looking for some of the highlights, here are our top recommendations. 

• Take a free walking tour. Listen to the myths, legends, and history of the city with a local.
• Explore the Square of Miracles. Historic square with four significant points of interest. 
• Take a food tour. Savor the flavors and simplicity of Pisan and Tuscan food.
• Go shopping in the Borgo Stretto district. Everything from Italian boutiques to western stores can be found in one of Pisa’s best shopping areas. 
• Gaze at the Keith Haring mural. This vibrant masterpiece is the final work of this famed modern artist.

11. Stroll through the Piazza del Campo in Siena

A city celebrated for its Gothic and medieval soul , Siena’s architecture, expansive art collections, and authenticity is an experience for all five of your senses.

It boasts the same points of interest as the most famous cities in Europe: impressive cathedrals, sprawling piazzas, and fine regional foods. 

However, Siena leaves more of a lasting impression as you can explore with a fraction of the crowds and modern refinements. 

Visit the lively, shell-shaped Piazza del Campo that serves as Siena’s social center. Explore the Siena Cathedral and its famed duomo. Or, if you can plan it, visit in July to watch the world-famous horse race, Palio.

Top things to do in Siena

As an embodiment of a medieval city, there are boundless points of interest in Siena.

• Marvel at the Duomo di Siena. Awe-inpsiring cathedral dome that rivals Bruneschelli in Florence. 
• Get lost in the historic center. The whole city center is a designated UNESCO World Heritage Site sewn together by walls, passageways, and streets.
• Climb Torre del Mangia. This tower dominates the city skyline and is one of the highest in Italy.
• Go on a food tour . A local will take you to the best spots in the city to sample wild boar, hare, Cinta Sense (pig), and many other regional delicacies. 
• Wander the Santa Maria della Scala. This former 1400s hospital is now a museum and culture center with Renaissance art, exhibits, and archaeological digs. 

12. Become an expert in gelato tasting

The ideal companion on any given afternoon in Italy is a scoop or two of gelato. Lucky for you, there are plenty of gelaterias to go around, so you’ll find plenty as you wander.

However, not all shops are created equal, so keep these tips in mind to find the best gelaterias:

• Check the ingredients. Look for sugar, cream, milk, and fruit flavoring. 
• Served out of steel bins. Avoid the tall piles.
• “Produzione propria” or “gelateria artigianale” . Indicates handmade gelato.
• Naturally colored. When in doubt, look at pistachio. It should be greenish-brown.

Insider tip: The best gelato in the world is found in San Gimignano at Gelateria Dondoli (see #15 on this list!)

13. Get familiar with Tuscan foods

Tuscany is a farming region, so its roots are in traditional peasant food. Rustic and simple, yet insanely flavorful.

These are some of the most popular Tuscan foods you need to try:

• Bistecca alla Fiorentina : A famous, rare t-bone steak seasoned with simple herbs.
• Crostini Toscani : The precursor to any Tuscan meal; chicken liver pate served on thin toasted bread.
• Pecorino Toscano : Tuscany’s signature hard cheese made from sheep’s milk. 
• Tagliatelle al tartufo : Long and thin pasta swirled into butter, garlic, and topped with freshly shaved truffle and parmigiano cheese.
• Biscotti di Prato : Hard biscuits to pair with espresso or dessert wine.
• Lampredotto: A typical Florentine street food made using the 4th stomach of a cow in a sandwich. 

14. Go on a Tuscan food tour

All over Tuscany there are a variety of food tours where you can discover true Tuscan cuisine and as an added bonus, they usually include wine!

Tuscany Wine & Food Tour with Guide

This Tuscany Wine and Food Tour gives you the best of both worlds at three different, organic wineries in the Chianti region .

Sample the finest wines, olive oil, balsamic vinegar, and foods made using authentic cultivation traditions from the region. As you indulge, gather knowledge about winemaking and this special region.

• Hours: 8 hours
• Price: $161.87 USD / person

“Our day trip from Florence to Tuscany was phenomenal. Our guide, Sofia, was funny, engaging, and knowledgeable. Each winery had their own uniqueness-you get to tour different parts of the wine making process and their estates….” – GetYourGuide Traveler (May 2023)

Chianti Wine & Food Safari

An adventurous way to get your grub on in Tuscany is aboard this Wine & Food Safari . 

In a rugged and custom 4×4 truck, you’ll travel down scenic back roads to tour and taste at a winery owned by one of the most prestigious Italian aristocratic families and a Chianti Classico vineyard .

• Hours: 10 hours
• Price: $200.98 USD / person

“Do not book any other wine tour. This tour was so unique and a wonderful experience I couldn’t imagine doing anything else. Latvi and Enrico we’re incredible!!! […] Unreal views and laughs. 100% recommend.” – GetYourGuide Traveler (April 2023)

15. Eat world-famous gelato in San Gimignano

The award-winning scoops of gelato in San Gimignano are among some of the best in the world.

In fact, a staple experience in this little medieval town is queuing up for your fair share of this sweet treat.

Most famously, though, Gelateria Dondoli is the talk of the town (and the world!) as people of all likes have traveled here just to eat this gelato. They have actually won the World Championship of Gelato multiple years and counting. 

You can’t go wrong with the classics, but be sure to check out their seasonal and experimental flavors once you get to the counter. I tried the Mango Sticky Rice and Grapefruit Sparkling Wine flavors and was in heaven !

16. Walk the ancient city walls of Lucca

Standing apart from other bustling metropolises like Florence, Milan, and Rome, Lucca is a breath of fresh air where you instantly feel at ease.

While compact, it’s bursting at the seams with the essentials of any quintessential Italian city : a medieval tower, cathedral centerpiece, impressive piazzas, and of course, its own signature cuisine.

But unlike other spots that need a concrete plan of action, a visit to Lucca thrives on a slower cadence and unhurried nature . One step within the city walls and you’ll be traveling in true Italian fashion.

Top things to do in Lucca

Within this famous walled city are plenty of sites to reel you into its charm.

• Walk or pedal the town walls. The symbol of the city that gave it its UNESCO status.
• Climb the Clock Tower for sweeping views of the entire city. 
• Visit the Lucca Cathedral. 11th-century seat of the archbishop with a treasury museum, medieval crucifix, and climb-worthy bell tower.
• Rent a bike and cruise the city. Two wheels is the best way to transit like a local in this laid back town.
• People watch at the Piazza Dell’anfiteatro. This elliptical-shaped square used to be a Roman amphitheater, but was redesigned and lined with shops, cafes, and restaurants in the 1800s. 
• Marvel at the Church of Saints Giovanni and Reparata. Uniquely placed church that sits on a partially exposed archaeological site.

17. Go on an olive oil tour

In a rural Tuscan farmhouse, you’ll join this Olive Oil Tour led by experts that have been making extra virgin olive oil since 1861 .

You’ll step into their world of oils as you tour their processes from cultivation and olive harvest, all the way to the bottle. Partake in an oil tasting using the techniques of oil sommeliers, then finish the tour with an unforgettable dinner paired with wine.

• Hours: 4 hours
• Price: $65 USD / person

“After this amazing olive tasting experience you will have a completely new perception and understanding of olive oil, and will think twice the next time you buy it in the supermarket. […] It was an unforgettable perfect time.” – Vera, Germany (September 2022)

18. Go horseback riding through vineyards

Traveling in Tuscany as they did in medieval times allows you to see so much more of this treasured region. These two tours take you to places few others have been able to see.

Horse riding among vineyards in Tuscany

In the tranquil hills of Montespertoli, this Horseback Riding Tour takes you through the evocative vineyards and olive groves of Tuscany .

As you take in nature, trotting along, you’ll also pass by a bertini forest, glittering lake, and storybook castle, Poppiano del Conte Guicciardini.

• Hours: 2.5 hours
• Price: $88 USD / person

“This was AMAZING! It’s the perfect way to see a lot of Tuscan countryside while having a fun and relaxing time. This experience was such a good value too, in the heart of Tuscany with beautiful views and great horses for a great price. […] The whole experience was such a highlight of our trip!” – Elyse (March 2023)

Tuscany Horseback Riding Tour with Wine Tasting

This Tuscany Horseback Riding Tour is taken to the next level when your stop for lunch doubles as a wine tasting. 

Start your tour in Ulignano, traversing native woods, lush vineyards, rolling olive groves, and byways of Tuscany to arrive at the Tenuta Torciano Winery. 

Feast on an authentic lunch with a complete menu of courses. Afterwards, join a wine tasting class where you sample Chianti, Chianti Classico, Super Tuscans, and more prestigious pours before meandering your way back through the countryside.

• Price: $233.57 USD / person

“Loved everything! The tour was very well organized. It was a hundred plus degree day in Florence but the countryside was not very comfortable. Would highly recommend” – GetYourGuide Traveler (June 2022)

19. Head to the beach

While Tuscany isn’t well-known for its beaches, it has its fair share of coastline that’s worthy for partaking in sunbathing and Italian beach culture.

Stretching from Versilia in the north to Argentario peninsula, there are many beaches to choose from, many of which have their own beach clubs.

• Island of Elba : Off the coast from the region in the Tuscan archipelago, this island has pebbled beaches and crystal clear waters reminiscent of the tropics.
• Versilia : This area is essentially one long, wide beach filled with lidos from Forte dei Marmi to Viareggio. It’s high-end and in its prime during the summer months.
• Cala del Gesso : One of the most stunning turquoise coves in all of Tuscany.

20. Learn about balsamic vinegar

A masterpiece of Italian culinary tradition , balsamic vinegar of Modena that is aged at least 12 or 25 years can be tasted at this Balsamic Vinegar Food Experience .  

During the tasting experience, you’ll sample 10 different kinds of aged vinegar and walk through the processes and techniques of what makes this variety so distinct. 

Book in advance at least 2 days and ask to extend the tour to taste typical dishes where the balsamic shines and have the opportunity to buy a bottle for yourself to take home.

“This was an absolutely amazing experience. Guido went above and beyond […] He was kind enough to share many special tastes of balsamic through every step of the aging process, even going so far as to allow us to try a few drops of the vinegar his father made for him when he was born. […] I would highly recommend it.” – Coleen (May 2023)

21. Check out the Chianti Sculpture Park

Deep in the forests near Siena, the Chianti Sculpture Park showcases 26 of the world’s best contemporary-sculpture artists and their installations sprawled across wooded grounds.

Walking along the pathways you can discover each one, entirely unique than the last, and ponder your favorite. 

22. Visit a castle or two

Tuscany is adorned with castles from Pisa to Arezzo that serve as standing pillars to the region’s history.

These are some of the most famous castles in Tuscany worth the drive or day trip to visit:

• Castello di Brolio : This 12th-century castle is the birthplace of Chianti wine. The winery, olive groves, museum, gardens, and restaurant are highlights of this family estate.
• This castle is currently closed to the public but the outside is still worth a visit.
• Castello di Banfi : On a hilltop surrounded by sprawling vineyards, this castle looks like it was pulled straight from a fairytale.

23. Go hiking in the Apuan Alps

Between the valleys of the Serchio and Magra rivers, the Apuan Alps are known worldwide for the Carrera marble used to sculpt some of the greatest artistic works in history.

Arts aside though, these mountains conceal more than a thousand underground karst caves like the Antro del Corchia and the Grotta del Vento, and offer miles of alpine hiking trails :

• Monte Sagro (Moderate): 5.5 km (3.4 miles)
• Pania della Croce (Moderate): 7.4 km (4.5 miles)
• Monte Tambura (Challenging): 11.7 km (7.1 miles)

24. Visit the Tarot Garden

Inspired by Gaudi’s Parco Guell, the colorful and quirky Tarot Garden described as an “ esoteric walk between nature and culture “ , was a 20-year art project by Niki de Saint Phalle.

On a visit, you’ll stroll among human and imaginative figures inspired by tarot cards, all colored in using mosaic-style patterns. The grounds offer a peaceful escape from the crowds as it’s one of the most unique and off-beat things to do in Tuscany.

• Entrance fee: €14.00
• Reservation required for entrance. You must purchase your ticket online .

25. Catch a sunset

Tuscany’s rolling verdant hills getting painted with brilliant golden hues is a staple way to conclude your days touring and tasting the region.

While you’ll be hard pressed to find a bad sunset spot in Tuscany, there are plenty of places that will make the final light of the day a bit more memorable. 

Before the sun sets, find your way to the top of a city bell tower, along city walls, anywhere in the countryside, or at panoramic vista point for the most eye candy.

How many days do you need in Tuscany?

As the largest region in Italy, you’ll want to carve out an ample chunk of time to explore Tuscany. 

While you can visit some of the highlights of Tuscany in just a few days, we’d recommend spending at least a week to really take it all in. 

With a week you’ll just scratch the surface, but with more time you can really slow down, explore, and take everything in. 

Best time to visit Tuscany

Tuscany is a year round travel destination, but some seasons are better than others for planning your trip.

The most popular time to visit Tuscany is June through August. However, we’d recommend avoiding the high season as prices go up, crowds are jam-packed, and temperatures can get very hot.

For optimal weather and fewer crowds, aim for mid-April to May and September to mid-October . Note September to October is the wine harvesting season in the Chianti wine region, so that, plus fall foliage, make these fantastic months to visit.

You can visit Tuscany in the winter and be welcomed with minimal crowds and cheap prices, however the cold and dreary weather may impact your visit.

Psst! Find out the best time to visit Italy based on seasonal weather patterns in each region and your personal travel style.

How to get to Tuscany

There are several ways to get to Tuscany, but the most common are flying or taking the train. 

The best way to get to Tuscany from elsewhere in Italy, is taking the train to Florence. Florence is the largest city in Tuscany and will likely be your hub for arrival and departure to and from the region. 

Here is a quick breakdown of the most popular routes. Book your train tickets via Trenitalia .

• From Rome: 1 hour, 45 minutes
• From Milan: 1 hour, 54 minutes 
• From Venice: 2 hours 13 minutes 

Insider Tip: You can use the Trenitalia app to book your train tickets up to immediately before boarding. Just be sure you enter the train station names in Italian. The main station in central Florence is Santa Maria Novella, listed as ‘Firenze S. M. Novella.’ Rome is ‘Roma – Termini,’ Milan is ‘Milano Centrale’ and Venice is ‘Venezia S. Lucia.’

If you are coming from outside the country, flying directly into the Florence International Airport (FLR) is an option. Be sure to check out our guide for how to get to Florence city center from the airport if you choose to fly. 

Otherwise you can fly into the Pisa International Airport (PSA), which is 88.1 km (54.7 miles) west of Florence and just under an hour on the high speed train.

How to get around Tuscany

It’s very easy to get around Tuscany as there is always a train, bus, or taxi that can take you to where you need to go .

Train travel in Tuscany

To get around to the larger cities, trains are the best method of transport. Trenitalia is the one stop shop for train tickets around the region. 

There are two main types of trains throughout Tuscany: high speed and commuter. 

As the name suggests, the high speed trains are fast! While these trains are often more comfortable, they are also more expensive. But if you’re looking to travel quickly across Italy, this is a great choice.

The commuter or regional trains are best for local travel and run frequently between smaller towns. This is the best option when planning day trips from Florence. They are much cheaper in comparison to the high speed trains and make for more scenic, albeit lengthier trips.

If you’re using commuter trains, it isn’t necessary to book tickets in advance, though it can be more convenient if you have the app. Alternatively, you can show up to the station a little early and purchase from the ticket office.

Bus travel in Tuscany

Where the trains don’t travel in Tuscany, there is likely a bus that does. Flixbus and Autolinee Toscane have affordable and convenient routes. 

Taxis in Tuscany

To get around the larger cities, taxis are an option. While the most expensive option, they can render useful since Uber is widely unavailable.

Getting a rental car in Tuscany

Having your own vehicle when visiting will give you a lot more freedom to explore the best things to do in Tuscany. It’s the only way to get to some of the more off-the-beaten-path destinations in the Tuscany countryside. 

We personally like using Discover Cars when we rent vehicles around the world, as they gather options from all sorts of rental companies in one place. It makes it really easy to compare prices and vehicles so you can determine which is the best option for you.

Search & Compare Rental Car Prices

• Discover Cars : We personally use this aggregate site to compare rental car prices from all the big name companies and get the best price possible. 
• Booking.com :  We’ve had good experiences finding rental cars with this site (formerly RentalCars.com) in the past. 

Insider Tip: If you are renting a vehicle when you are already in Florence, the best option is to rent from the airport and take the tram there from the city center (SMN station). The tram costs just €1.50, as opposed to a taxi ride which will run you about €25. (I learned this lesson the hard way *face palm*)

Tips for visiting Tuscany

Here are some things to keep in mind for your trip to Tuscany.

• Take things slow. Embrace the Italian pace and know you won’t see absolutely everything on your first visit.
• Keep cash on you. Cards are widely accepted, however small shops still take cash. Plus, it’s nice for smaller purchases. 
• Book attractions/accommodation well in advance. Especially in major cities like Pisa and Florence during the summer high season. Start looking at tickets and hotels at least 6 months in advance to avoid premium pricing and limited options.

Where to stay in Tuscany

Florence is the capital of Tuscany and well-connected to the rest of the region, so it makes an ideal base for you to use as you explore. Many of Tuscany’s top sights can even be done as day trips from Florence.

However, there are other cities in the region that are worth checking out. Most notably, Pisa, Lucca, and Siena. The former have access to the northern part of the region, while Siena is based near the Chianti wine region and jewels in the south.

Budget hostel in Florence: Hostel Archi Rossi

Situated in the historic city center, this hostel is close to all the main attractions in the city, including the main train station. There are private and shared rooms, an outdoor garden patio, washer and dryer facilities, free coffee, cafeteria, and clean rooms.

Mid-range couples stay in Lucca: Luxury Corte Di Re Artù

Medieval and unique, this bed and breakfast is a gem just a stone’s throw from Lucca’s historic center. It’s situated in a 19th-century building, but still has modern day comforts: AC, free Wifi, a relaxing garden, scenic patio, excellent location to all the main landmarks. 

Agriturismo stay in Siena: Pensieri di Cavatina

You’ll discover true Tuscan living at this farm stay just east of Siena. Hands down, the highlight of this stay are the views of rolling hills and vineyards for miles. It comes with everything you’ll need for a comfortable stay: full-service kitchen, onsite restaurant, washer, private garden, terrace, and free Wifi.

Mid-range budget option in Pisa: Elegant Apartment

This spacious and bright apartment makes you feel like a local with its location near the central train station, airport, and Leaning Tower. It’s recently updated with 3 balconies, a full-service kitchen, spacious living areas, and free Wifi. Plus, it’s connected to the airport every 5-minutes by electric shuttle.

Splurge hotel in Florence: Grand Hotel Baglioni

This luxurious hotel is conveniently located just across the street from the train station within the history center. Elegant rooms, a breakfast buffet, rooftop garden, and free Wifi are steps away from all the best restaurants and attractions of Florence.

What to pack for traveling to Tuscany

There are a variety of different activities you’ll want to pack for when visiting Tuscany. Here are a few essentials you don’t want to forget.

• Comfortable walking shoes
• Insulated water bottle
• Sun protection: sunglasses, hat, and sunscreen
• Light shawl or scarf (for religious buildings)
• Microfiber travel towel
• International SIM card
• Camera (this is our favorite portable tripod for travel !)

Be sure to download our  complete packing list for Italy !  It’s packed with good suggestions and  insider tips  to help plan your Italy trip. And it’s completely  FREE , so why not!?

Round up of the best things to do in Tuscany

Here’s a recap of all the best things to do in Tuscany so you can see everything in one place.

• Ride a vintage Vespa through the Tuscan countryside
• Road trip through the Val d’Orcia
• Soak in a natural hot spring
• Float in a hot air balloon over Tuscany
• Test your skills at truffle hunting
• Leaning Tower of Pisa
• Stroll through the Piazza del Campo in Siena
• Become an expert in gelato tasting
• Get familiar with Tuscan foods
• Go on a Tuscan food tour
• Eat world-famous gelato in San Gimignano
• Walk the ancient city walls of Lucca
• Olive oil tour
• Go horseback riding through vineyards
• Island of Elba
• Balsamic vinegar food experience
• Chianti Sculpture Park
• Visit a castle or two
• Go hiking in the Apuan Alps
• Visit Tarot Garden
• Catch a sunset

Are you planning a trip to Italy?

We have lots of resources on travel in Italy and destinations throughout the country. Check out our  Italy Homepage  for everything you need to know, or start by reading some of our favorite Italy articles here:

• Classic 10-day Italy Itinerary
• Best Day Trips from Florence
• Cinque Terre National Park: Ultimate Guide + Tips
• Best Things to Do in Florence (you won’t want to miss!)

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We want to hear from you!

Have you ever been to Tuscany before? What was your experience like? Which of these things to do in Tuscany are going straight to the top of your bucket list? Leave your comment below and we’ll do our best to get back to you!

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17 Best Day Tours In Tuscany You Will Love (Wine, Culture, and More!)

September 6, 2022 //  by  Follow Me Away //   Leave a Comment

Are you searching for the best Tuscany tours?

If you want to take a tour while you are in Tuscany but are afraid of paying too much or having a terrible or boring experience, rest easy!

Touring Tuscany with a professional guide is a great option if you are looking to see and experience the best without doing a ton of planning on your own.

We have been to Tuscany multiple times and have compiled this list of trustworthy tour operators in Tuscany who are worth every penny.

Whether you are taking a Tuscany road trip and want to add on some local tours, you are stopping in Italy on a cruise, or you visiting during your Italy itinerary , tours in Tuscany have the option to enrich your experience.

These best tours in Tuscany will provide you with enough options from group and private tours to half and full-day options so you can choose the tour that best suits your trip to Italy.

Whether you are looking for wine tours in Tuscany or want to see the historic sites , this region of Italy has something for everyone!

If you are looking for a trusted place to find the best Tuscany tours, get ready to find them all in one place.

Don’t forget to check out our list of the best places to stay in Tuscany !

Small Group Wine Tasting Tour to Tuscany (4.5 Hours)

Be honest, one of your main reasons for visiting Italy is to sip on some fine wine!

There are many Tuscany wine tours from Florence, and we will feature a few favorites today. Make sure to check out our list of the Best Places to Stay In Florence!

This Small Group Wine Tasting Tour to Tuscany is the perfect introduction to Tuscan wine culture.

On this wine tour in Tuscany, you will visit two wineries where you can enjoy wine paired with local produce.

The duration of the tour is just long enough for you to get a great feel for wineries in Tuscany without going overboard.

You will get to experience some historic culture and tour wineries during your time in the Chianti Classico wine region.

A wine tasting in Tuscany is a romantic thing to do during a Tuscany honeymoon !

Reserve your tour: From Florence: Small Group Wine Tasting Tour to Tuscany

You May Also Like: Siena Educational Wine Tour And Tasting (3 Hours)

Florence: Siena, San Gimignano, & Monteriggioni Day Tour (11 Hours)

Florence is a wonderful base for many of the best Tuscany tours. It is centrally located and the most popular and well-known city in Tuscany.

The Siena, San Gimignano, & Monteriggioni Day Tour will show you what the best three ancient Tuscan cities have to offer.

This tour in Tuscany is not for the faint of heart as it is a full-day tour.

That said, you will be traveling through the Tuscan hills in an air-conditioned luxury motorcoach and will have a live guide.

The best part? This tour is both historic and tasty!

If you are looking for a Tuscany wine tour and historic tour all in one, this option is the perfect choice for you as you will receive two exclusive Tuscan wine tastings.

You will love exploring these beautiful small towns in Italy on one of the best tours to Tuscany from Florence!

Reserve Your Tour Here:   Florence: Siena, San Gimignano, & Monteriggioni Day Tour

You may also love:  Montepulciano Wine Tasting and Cellar Tour (1 hour)

Pizza & Gelato Preparation Tour in Florence (3 Hours)

If you are looking for a Tuscany tour that offers something a little different and unique, then you will love this  Pizza & Gelato Preparation Class in Florence.

There is nothing better than an enjoyable day finished off with a delicious meal and the best souvenir you can bring home, the skills to recreate the dish on your own!

Not only will you learn to make classic Tuscan pizza, but you will also learn the Florentine way of preparing gelato.

This cooking tour is set in the late afternoon so while your pizza cooks you can sip a glass of included wine and enjoy an early evening meal.

Your tour guide will be a famous local chef who knows the ins and outs of Tuscan cooking. What a memorable experience!

Book Your Tour Now:  Pizza & Gelato Preparation Class in Florence (3 Hours)

You may also love: Florence: Cooking with Kids 3-Hour Experience

Pisa City Center: 2-Hour Private Tour (2 Hours)

You have heard about this famous city for years and now you will finally get to see it on this Pisa City Center: 2-Hour Private Tour .

If you prefer a personalized tour, this option is perfect for you as it is set up for 2 guests.

You will explore the Piazza dei Miracoli, admire Pisan monuments, visit the Cathedral of Pisa, and learn about Galileo’s life throughout your tour with a private guide.

You will be able to stop and ask questions, photograph, and spend time at each monument as you wish while touring in Tuscany.

All of your entrance tickets are included in the price of the tour so you will be set to go from the moment you arrive until the moment the tour concludes.

Reserve now:   Pisa City Center: 2-Hour Private Tour (2 Hours )

If you are coming from a cruise: From Livorno: Bus Transfer to the Leaning Tower of Pisa

Tuscany Truffle Hunting with Wine and Lunch (3 Hours)

If you are looking for a really unique Tuscan experience, then you need to book this Tuscany Truffle Hunting with Wine and Lunch tour!

On this tour, you will head into the forest with a knowledgeable guide and truffle hunting dogs.

If you are looking for some fun, cottagecore vibes, you cannot miss out on this opportunity!

After searching for truffles, you will enjoy a delicious 4-course lunch with a wine tasting.

This is will be the highlight of your time in Tuscany! Who doesn’t like running around a forest with dogs?

Book Here: San Gimignano: Tuscany Truffle Hunting with Wine and Lunch

Guided Walking Tour Of Florence (2.5 Hours)

Florence is the birthplace of the Renaissance and a Guided Walking Tour is the perfect introduction.

The best way to explore any city is to walk through it and the experience is even better when you are accompanied by a knowledgeable local guide.

On this 2.5 hour Florentine Tour , you will be able to see fantastic monuments such as the Ponte Vecchio bridge and the Basilica di Santa Croce all while learning about Florence’s journey through the Renaissance.

This easy Tuscany tour is a great morning or afternoon excursion before lunch or dinner and the cost won’t break the bank either so you have some extra cash for another class of wine!

After the walking tour, go take a tour of the Duomo ! It is a can’t-miss site in Florence.

Reserve now: Guided Walking Tour Of Florence (2.5 Hours)

You may also like: Private Tour Of Florence (4 hours)

Chianti Afternoon Tuscany Wine Tour (5 Hours)

This focused Tuscany wine tour will take you through the beautiful Chianti wine region where you will see vineyards unfold before your very eyes.

During the  Chianti Afternoon Tuscany Wine Tour , you will enjoy delicious Chianti wines, Tuscan products, and rolling hills and vineyards.

You will stop at two wineries and will visit two historic wine cellars to learn about how Chianti wine is made.

You will also have the chance to try cured meats and cheeses along with your wines.

The best part of this tour is that you will be able to see one of the oldest medieval walled cities in Italy.

As far as wine tours in Tuscany go, this one ticks all the boxes for food, flavor, and fun for anyone who loves wine!

Book your wine tour now:   Chianti Afternoon Tuscany Wine Tour (3 Hours)

Florence Hop-on Hop-off Bus Tour (24 Hours)

Florence is one of those cities you want to learn everything about!

What better way to do that than on this  Florence Hop-on Hop-off Bus Tour ?

This is one of the only Tuscany tours of this kind, so if you love bus tours, this will be the one to book.

Of course, walking through the city is great, but we particularly love hop-on-hop-off bus tours because they allow you to see the major sites of the city without having to worry about transportation or directions.

While you are riding on this bus tour in Tuscany, you will also have an expert local guide who will point out sites along the way and in-between destinations!

You can purchase tickets good for 24, 48, or 72 hours depending on the length of time you want to allow for this Tuscany tour.

This tour will help you see all the amazing things to do in Florence !

Reserve here:   Florence Hop-on Hop-off Bus Tour

Carrara Marble Quarries Tour by Jeep (2.5 Hours)

Looking to break up the wine and cheese with one of the more adventurous Tuscany tours?

The  Carrara Marble Quarries Tour by Jeep is a whirlwind 2.5-hour adventure that you will most certainly be writing home about.

We bet that you have probably never even heard of the Tuscan Carrara Marble Quarries before this post, and you are going to love this hidden gem in Italy .

These mines have provided marble to Italy for centuries and many cities utilized the marble including Rome.

Your 4WD adventure will take you into two quarries, including an underground one.

You will also have the chance to taste some Lardo di Colonnata IGP during one of the more unique Tuscany tours.

Book now:   Colonnata: Carrara Marble Quarries Tour by Jeep

Pisa, Siena & San Gimignano Day Trip with Lunch & Siena Tour with Cathedral (12 Hours)

Short on time or just don’t want to beat around the bush?

This  Pisa, Siena & San Gimignano Day Trip with Lunch & Siena Tour with Cathedral will show you the best of what Tuscany has to offer all on one tour.

One of the most comprehensive day tours in Tuscany, this tour will show you Pisa, San Gimignano, and Siena which are some of the most beautiful cities in the region.

If you don’t have time for one of the many Tuscany wine tours, don’t worry, there is a wine tasting on this tour as well.

Your admission fees are included and you will eat a Tuscan lunch at a winery on this full-day tour in Tuscany.

One of the things that set this tour apart from other Tuscany tours is that you have the option to book pick-up on demand which means the tour company will pick you up from your hotel.

Overall, this is one of the Florence to Pisa tours if you want to check out the famous city.

Reserve Here:   From Florence: Pisa, Siena & San Gimignano Day Trip with Lunch & Siena Tour with Cathedral

You May Also Love: Brunello di Montalcino Full-Day Wine Tour with Tastings

Medici Family History Tour (2 Hours)

If you are looking for something fun and informative to do, the Medici Family History Tour may be perfect for you!

While visiting the Palazzo Medici, a famous architectural work of the fifteenth century, you get to also visit a secret place where Michelangelo learned to sculpt during this adventure.

This symbolic tour lets history buffs relive the betrayal and victories of the famous Medici family while exploring some of the most famous architectural buildings and also visiting where many scenes of the TV series “The Medici” took place!

If you’re a fan of the show, we highly recommend checking this out!

Book Here: Florence: Medici Family History Tour

Florence: Evening Food Tour (3.5 Hours)

There is no denying the fact that one of the best things about visiting Italy is the food, so is there a better way to enjoy Tuscany tours other than by booking a food tour?!

The Florence Evening Food Tour is unique, as you and your small group can explore the other side of Florence, which is called the Oltrarno, to experience a less-than-touristy night of mouthwatering food.

While you will be walking a bit during this tour, you also get to explore the ancient and medieval neighborhoods around the Oltrarno area in addition to getting to know genuine Italian food traditions and local, craft beer.

Of all the best tours in Tuscany, this one lets you eat your heart out: from cured meat and cheese, to beer samples, to family-owned bakeries and more, you will leave feeling stuffed!

This is one of the most delicious and best tours in Florence, Italy!

Book Here: Florence: Food Evening Tour

Museo Galileo Small Group Tour (1.5 Hours)

If you are looking for a fun and unique Tuscany tour, you might want to consider checking out the Museo Galileo Small Group Tour .

The Museo Galileo is one of the most famous international institutions dedicated to the history of science.

On this 90-minute small-group tour, an official guide will reveal all of this museum’s secrets to you.

From getting to know some of the scientific tools made by Galileo himself, this Tuscany tour lets you set back in time to admire science and history and is perfect for a short tour/adventure to squeeze in between your sightseeing adventures!

This is one of the best Tuscany small group tours!

Book Here: Florence: Museo Galileo Small Group Tour

Inferno Florence Private 3-Hour Tour (3 Hours)

There’s no denying the fact that Florence is a city full of mysteries and secrets, and Tuscany tours like the Inferno Florence Private 3-Hour Tour allow you to explore the city’s secrets in a unique and unusual way.

During this tour, you can follow the “main character” of Dante Alighieri’s Inferno on his adventures, exploring the nine circles, seven sins, and one terrifying secret.

This private tour is fun and mixes history, literature, science, and art together while immersing yourself in Florence.

From learning about the Middle Ages to exploring the Palazzo Vecchio and Baptistry, this is a guided tour in Tuscany you may not want to miss!

Book Here: Inferno Florence Private 3-Hour Tour 

Chianti and Castles Tour with Wine Tastings (5 Hours)

The sounds, scents, and flavors of Chianti will capture your senses, and this is a must-do Tuscany tour, as it is one of the best Tuscany wine tours around.

Expert tour guides will lead you around the uncontaminated landscapes of the Chianti area and you’ll get to visit these vineyards that are well known for their color– so make sure to bring your camera!

But better yet, this Chianti and Castles Tour with Wine Tastings also lets you explore ancient churches, medieval Tuscan castles , and small villages throughout your five-hour adventure.

From trying bruschetta to wine tasting to visiting historical buildings and breathtaking landscapes, this is one of the best Siena tours to choose from!

Book Here: From Siena: Chianti and Castles Tour with Wine Tastings

Discover Cinque Terre From Florence (13 Hours)

If you don’t mind long Tuscany tours and are looking for a slice of paradise during your trip, you might want to check out the Cinque Terre Full-Day Trip !

This tour lets you discover the hidden gems of the Cinque Terre regions, allowing you to explore the ancient fishing villages of Manarola, Riomaggiore, Monterosso, and Vernazza.

Spend time marveling at the rocky coast of the Ligurian Sea.

It is breathtaking and offers fantastic seaside views that you may want to check out.

The seaside is wonderful, and be careful, because once you visit, you may not want to leave!

There are so many fun things to do in Cinque Terre ! Plus, there are a bunch of beautiful places to stay in Cinque Terre on your next visit!

Book Here: From Florence: Cinque Terre Full-Day Trip

Visit the Accademia Gallery with Reserved Entrance (1 Hour)

If you are visiting Tuscany and Florence, stopping by the Accademia Gallery is a must! It is one of the best things to do in Italy !

This Tuscany tour will only take about an hour of your day, as the Accademia Gallery: Tour is the perfect one-stop-see-all moment!

This tour lets you discover and understand the creation of Michelangelo’s famous masterpieces and lets you explore the halls of the Accademia gallery, which are filled with Florentine paintings from the 15th century.

With this relaxed yet informative atmosphere, this is the perfect tour for art lovers and helps you cross off some of the most iconic sights to see in a short period of time!

Seeing David in person is one of the top things to do in Tuscany , so you cannot miss out on this tour!

Book Here: Accademia Gallery: Tour

Whether you are looking for wine, adventure, or culture, these best Tuscany tours offer something for everyone.

All of these guided tours in Tuscany are worth every penny and you will not be disappointed.

They are also quite affordable for what they offer so you can’t go wrong no matter which tour in Tuscany you choose.

Which one of these Tuscany tours are you most excited about? Let us know in the comments below!

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21 Best Towns in Tuscany + 7 Unique Day Trips (2023 Guide)

Looking for the best towns in Tuscany?

Oh Tuscany, the land of picturesque green rolling hills, paths lined with olive trees, vineyards as far as the eye can see, and charming Tuscan villages. We have enjoyed spending time exploring the best towns in Tuscany with our kids on two separate occasions.  This time, we ventured for 3 months around Tuscany, Italy while our kids attend a world school in Pistoia (a lesser-known city in Tuscany).  

Per usual, we love to journey out by car or train, exploring not only the well-known Tuscany sites but also the small towns in Tuscany—the ones that don’t always make the main lists of Best Towns in Tuscany !  

Here, you’ll find some new ideas for day trips in Tuscany and just outside of Tuscany.

Our content is reader supported, meaning that at no additional cost to you, we may receive a commission if you click through and make a purchase from some of our links. For more information, read our disclosure here .

Traveling Throughout Tuscany Tips

Note that some towns in Tuscany are quite easily reached by train, while others really do require renting a car or hiring transportation.  Hiring drivers in Tuscany is not cheap and if you are planning to rent a car during high season, make sure to reserve one ahead of time.

💡 TIP: If you don’t know how to drive a Manual, make sure you check that your rental car location has Automatic cars!

BEFORE YOU GO :  Download the App:  TrainLine

This lets you book your train travel from your phone!  While most of the time you can just walk up and purchase a ticket, there are times when the line is long. Also, note that during the high season or holidays, you’ll want to book your important train tickets in advance . 

Ready to Plan? Check out these Travel Resources!

Safety Wing has been our go-to for trip insurance over the last few years. They are affordable and it’s easy to receive a quick quote.

Booking.com is the platform we use most often for booking accommodations!

Best Towns in Tuscany to Visit

Not only will you find a list of the best towns in Tuscany, but you’ll also find other great day trips and experiences for your vacation.

If you plan to stay overnight in any of these towns, I usually start with booking.com to seek out the best accommodations in Italy.

I recommend basing yourself somewhere and taking day trips from there.  Anything around Florence is quite central. Although Florence is increasingly more and more crowded so if it were me, I’d choose a less crowded town.  

We loved being based in Pistoia . This small city is less crowded and has easy train access. We also rented a car from the Hertz location in town. Just note that the car rental locations in the smaller towns aren’t typically open on the weekends. 

THINGS TO KNOW BEFORE DRIVING IN ITALY

👉 There are lots of toll roads in Italy. You can pay for tolls by credit card.

👉 There are camera speeding traps all over. Signs are placed so you’ll know they are present. Another indication is when traffic slows down.

👉 Most cars are manual. So if you need an automatic car, reserve it ahead of time to make sure there is one available.

👉 Most of the beautiful towns in Tuscany have a historic center in which rental cars are NOT allowed to drive.

👉 Parking can be tricky. Usually on the outskirts of town, there are free parking spots or paid parking lots.

Now onto the list of the best towns in Tuscany to help you plan your incredible trip to Italy!

1. Montecatini AND Montecatini Alto

Located between Florence and the beaches is the charming town of Montecatini Terme with enticing thermal pools and a pretty promenade. 

Plus, you get a bonus by being able to explore the cool medieval town, located on Montecatini Alto on the hilltop of Montecatini.

Montecatini Alto is the supersmall but scenic village on top of the mountain. There is a main piazza with restaurants to choose from and gelato for good measure. We ate a nice lunch and enjoyed the sunny piazza before wandering around to explore more.

💡 NOTE:   Most of the lunch places don’t start serving food before 12:00, however, there are a couple of spots that serve an early lunch!

There is a church at one end of town and a clock tower at the other.  Both sides of the skinny village hold gorgeous panoramic vistas of the Tuscan hills and valleys below. 

We really enjoyed our short trip there and would recommend it for a half-day excursion. Montecatini Terme is also nice to walk through the pedestrian zone of shops and cafes!

How to Get to Montecatini

Train:  Easy train trip !  

There are 2 train stops for Montecatini, you can take either.

We chose the 2nd (“Montecatini Centro”) but were penalized with a 10-minute wait while another train had to pass by. We have since realized that this happens regularly, so if you are coming from Florence, it may be worth getting off at the first stop “Montecatini Terme”.

If you are coming from Viareggio, get off at Montecatini Centro.

Things to Do in Montecatini & Montecatini Alto

✔️ Ride the Funicular Train

Our mission was to ride the funicular, so we charted a walk straight through the main promenade to get to the funicular train station (~15-20 minute stroll). 

Even though the scheduled times for this inclined train are every 30 minutes, the funicular leaves whenever it feels full or when they feel like it.

The cost to ride Montecatini Alto Funicular is €7.50 roundtrip per adult and €4 for kids 6-10yo.  

THINGS TO NOTE

👉 There is a free 1 stall bathroom at the station.

👉 The funicular train in Montecatini takes a break from 1:00-2:30 (13:00 – 14:30). Yes, the funicular has a siesta too so plan accordingly!

👉 Grab a front or back (outdoor!) standing spot on the Funicular Train for the best views. The ride up is smooth and the view opens up as you approach the top station. 

✔️ Take a Hike

You can also opt to walk down from Montecatini Alto to Montecatini if you want to skip the Funicular ride both ways. 

And if you’re heading back down to Montecatini, you can meander through the pedestrian zone of shops and cafes.

✔️ Relax at a Thermal Spa

You can also choose to spend the afternoon at the Thermal Spa. Terme Tettuccio is one of the main thermal spas with absolutely gorgeous architecture and grounds.

Where to Stay in Montecatini

We didn’t stay in Montecatini, as we were based in nearby Pistoia. However, there were some beautiful hotels (mansion style) and B&B that you can check out if you want to base yourself in Montecatini.

I recommend booking your accommodation in advance on Booking.com .

As one of the Tuscan towns with the most tour groups parading through, it is crucial to plan wisely for your visit to Siena.

How to Get to Siena

Recommended Car Trip.  A popular tourist town!

The location makes it not a direct nor short train trip from where we were staying in Pistoia, so we rented a car on a weekday to make a day trip out of it. 

Note that most of the roads to Siena are toll roads and paying by credit card is easiest!

Parking in Siena

We pulled in straight to a parking garage (Parcheggio Santa Caterina at €2/hour). It’s strategically located near the public escalators that cleverly and kindly coast you up to the hilltop town. This is especially nice for those with mobility issues.

Things to Do in Siena

There are 3 main attractions for us:

✔️ The heavily adorned Santa Maria della Scala cathedral .

✔️ The sprawling Piazza del Campo where the Palio di Siena horse race takes place in July and August.

✔️ The gently winding street of shops for eats and treats of Via di Citta .

Tips for Visiting Siena

👉 Arrive as early as possible to beat the tour buses. 👉 There are many tourist-catering restaurants on the piazza to sit for a meal and imagine the jockeys careening the horses around each corner of the piazza. 👉 When leaving the parking garage there is a pay station up top to slide in your ticket to pay, you then have 15m to exit.

💡 FUN FACT : The symbol of Siena is the she-wolf nursing Romulus and Remus

Where to Stay in Siena

I would recommend checking out Booking.com for the best hotels to meet your budget!

3. San Marino – A country within Italy!

Okay, okay, it’s not exactly a town in Tuscany, but it is A COUNTRY within Italy that isn’t the Vatican!

You can check another country off your list with a visit to this tiny nation completely surrounded and landlocked by Italy.

Located towards the east coast town of Rimini, this city-state has been independent since the early 300s. It’s not accessible by train, so a rental car is your best bet to get you to this medieval hilltop city center.

This fifth-smallest country in the world, San Marino has the oldest constitutional republic in the world dating back to 1600. If you stay long enough you may be eligible to be head of state. Every six months 2 captains regents from opposite parties are elected to share this post. 

How to Get to San Marino

By car is definitely the easiest, as it is about a 3-hour car ride from Florence.

Parking in San Marino

We had plans to park in a lot near the top gate, but on a Saturday there were police directing/forcing tourists to park in a lower lot. It’s actually quite nice that they had police directing instead of a bunch of tourists not knowing where to go!

Things to Do in San Marino

Here are some fun things to do while visiting San Marino.

✔️ Ride a Tourist Train/Bus: Fun for Kids!

This worked out just fine as there was a cute tourist train/bus outside the garage that rode us up to the top for 3 euro per adult and big kids. 

💡 NOTE:   There is also a cable car from a lower spot we hadn’t known about which looked to be a splendid way to transport you up.

But there were no parking spots for it by the time we got there. I’d vote to try this route if you have the option to.

✔️ Stroll Through the City and Castles

The castle walls and city center are quite charming with a pedestrian promenade of shops and restaurants to wander up and down the stone streets. The castle towers have an entry fee, but a package deal allows entry into all of them. 

We scored a rainy day, so we opted to not pay for the outdoor castle grounds entry fee and instead explored the shops. We then had lunch until the raindrops were held so we could admire the panoramic vistas and hike the castle walls that are publicly accessible, which occupied us for the afternoon.  

We had other plans, but imagine it would be an amazing sunset and/or sunrise if you have the chance to stay in the evening or overnight. The city is perched on a super high hill which is really impressive to see coming or going. 

💡 FUN FACT:   Apparently, because of its strategic hard-to-reach hilltop location, Napoleon declared he would not conquer San Marino, one of the many reasons the country still exists today.

✔️ Walk Down the Hill

We chose to walk back to the parking garage instead of paying for the tourist train back. We meandered down a twisting series of streets lined with shops, a very relaxing and peaceful stroll down the hill. 

✔️ Explore Unique Museums

If you love museums, especially weird unique museums, San Marino is known for its variety of interesting museums that you can check out all over the town/country!

Overall it is definitely lengthy for a day trip, but exciting to visit another country!  Plus, it was really fun walking along the high castle walls and skipping in and out of the shops.

Where to Stay in San Marino

Check out Booking.com for the best hotels to meet your budget. We suggest staying in the old town to be able to walk to all the cute shops and cafes.

4. Pennabilli

Since we mentioned San Marino as a fun Day Trip from Tuscany, we need to mention this small village of Pennabilli, which makes a perfect stop on the way to or from San Marino from Tuscany.  

This is definitely off the tourist route and you’ll need a car to get to Pennabilli . But it’s worth it and here is why.

We chose the slow scenic route back from San Marino and this little quaint town of Pennabilli was less than an hour away.

The only reason we knew to find this gentle gem was because of a podcast episode that proves you can find love late in life; you can show up for your partner no matter the distance; you can find purpose after loss; and you can find the sounds of silence if you roam around Italy long enough.

If you are a fan of Phoebe Judge (narrator) or just a fan of love, give this a listen here .

How to Get to Pennabilli

Get there by car. It’s just under 1 hour from San Marino and 2.5 to 3 hours from Florence.

Parking in Pennabilli is easy and free just off the historic center. 

Things to Do in Pennabilli

✔️ Explore the Main Piazza

This small Italian village proved true to be a quiet one with no fanfare and easy access to explore away. The principal piazza has a friendly fountain, a cherished church, a poppin’ pizza place, and gooey gelato—basically the core ingredients of an Italian village and everything you actually need in life.

As we wandered betwixt the alleys up and down we kept uncovering hidden wonders just beneath the surface. 

✔️ Connect with Nature

First, we stopped at a lookout to hold our breath to hear every single sound of the nature surrounding us. This land is calm and serene and natural and proud and unapologetic and unbothered by the faster pace of the world around it. 

✔️ Bell of Lhasa

Next, we stumbled upon the Bell of Lhasa which was commemorated by the Dalai Lama himself nearly 20 years ago. A random little piece of Tibet in Italy!

✔️ Be Amazed at the Place that Inspired the Background of Mona Lisa

THIS!!! Finally, we found the background scene of the Mona Lisa. This landscape was one of da Vinci’s fond favorites such that he included it in his masterpiece.

Yes, you can actually see the landscape from the Mona Lisa firsthand from a hilltop in Pennabilli.

As a stop along the way of our other adventures, it was a peaceful unvisited marvel that we truly enjoyed. 

✔️ BONUS: A Waterfall Stop: Cascata del Presalino

If you commit to the slow scenic route back from Pennabilli to the Florence area, be sure to catch the roadside stop-off to get wet in the waterfall of Cascata del Presalino! 

The whole drive is stunning up and down and all around this land where these 4 regions meet: Emilia-Romagna + Umbria + Marche + Toscana.

Where to Stay in Pennabilli

If you want peace and quiet and are away from lots of distractions, Pennabilli could be the quaint Italian village for you. I’d start with Booking.com to see options for accommodations in Pennabilli.

Some of the top-rated accommodations in Pennabilli include Hotel Il Duca Del Montefeltro and B&B Fonte Dei Billi .

Pistoia is located about 40 minutes outside of Florence, easily accessible by train. It’s a lesser-known town, which means it is less crowded (cue the smiles), yet has a lot of amenities of a city. 

We were based in Pistoia for 3 months at a world school called Boundless Life . During this time, we did a lot of exploring in the city, as well as the surrounding area! We travel full time, so exploring is part of our kids’ worldschool curriculum !

How to Get to Pistoia

It is easiest to take a train , which puts you right in the middle of the city and only a 10-minute flat walk to the historic center. 

You can drive, just know that like most Italian cities, there is a historic center where you can’t drive in or you will get fined. Parking can also be an issue. Although we had no issue finding parking on the outskirts of town, especially on the main street in front of the supermarket, Esselunga.

If you want to rent a car in Pistoia, you will only be able to rent a manual, as they rarely have automatics to rent. And note, that they usually close early on Saturdays and are closed on Sundays.

Things to Do in Pistoia

Below are a few things to do in Pistoia. If you are looking for a more in-depth overview of Pistoia, make sure to check out our post on all the best things in Pistoia .

✔️ Stroll through the Town

Walk through the historic center and meander in and out of shops. Stop for a coffee & croissant at Pasticceria Armando, and grab lunch at my favorite: Locanda del Capitano . There are many restaurants to choose from in Pistoia .

✔️ Visit the Street Market

On Wednesday and Saturday mornings from about 9-1 pm, vendors will the streets selling all sorts of goods, as well as produce. 

✔️ Explore the Zoo

To be honest, I’m not a huge fan of zoos. But, Pistoia has a nice zoo just outside of town.

✔️ Join a Cooking Class and Olive Oil Tasting

Set up a cooking class and olive oil tasting with the owner of Podere Macolo.

Where to Stay in Pistoia

I would absolutely stay at Palazzo 42 . It’s in the heart of town, nice rooms and friends that have stayed there have all loved it.

A popular Tuscany town that earns a spot on most lists of Tuscany’s best. And rightfully so. Lucca is known for being able to ride atop the city walls around the old town.

How to Get to Lucca

As always, you can drive. But Lucca is right on the train route so it’s much easier to catch a train since you don’t have to deal with parking.  The train takes approximately 90 minutes from Florence (Firenze).

Things to Do in Lucca

There are many things to do in Lucca. Here are some of our top picks.

✔️ Ride a Bike

When you exit the train station, there is a bike rental shop where you can rent bikes or these quad and … 

We rented this one for our family of 5 + my parents. It was an absolute blast riding along the entire city wall. For reference, in one of these 6-person bikes, you can do the city wall in an hour, although you really can’t waste much time.  

Where to Stay in Lucca

I recommend checking checking out Lucca in Villa Lucrezia or Hotel San Marco .

7. Montepulciano

Montepulciano is a medieval town that sits on top of a hill in southern Tuscany. Its beautiful location comes with an abundance of elegant palaces from the Renaissance period, ancient churches, vast vineyards, charming squares, and panoramic views of the Val d’Orcia and Val di Chiana valleys.

I recommend touring around this town on foot since it has many beautiful hidden corners on top of its popular landmarks. The town is also not too crowded although it has become a more popular tourist attraction after the movie New Moon was shot there.

How to Get to Montepulciano

You can get to Montepulciano via car, bus, or train.

How to Get to Montepulciano by Car

I recommend traveling by car to Montepulciano for convenience and better control over your time. If you’re coming from Siena, you can take the scenic route by going south through the Val d’Orcia on the SS2 to San Quirico d’Orcia. You’ll then have to take SS146 through Pienza until you reach Montepulciano.

💡 NOTE:   The town’s historic center is closed to traffic. This means you’ll have to park outside the town center unless you have a permit.

You can find several convenient parking lots on the edge of the town. They are well-marked so you can spot them with no problem. The parking fee can be about €1.20 every hour.

How to Get to Montepulciano by Train and Bus

If you prefer public transportation instead of driving, you can ride buses and trains to Montepulciano. The closest train station sits outside of the town and you will still need to ride a bus to reach Montepulciano.

There are buses that run hourly from Chiusi train station . You can catch a bus every 1 and a half hours from Siena. To reach the historic center from the bus station, you can either walk or ride the small orange bus.

💡 NOTE:   Keep in mind that the buses may not run on Sundays.

Things to Do in Montepulciano

Make sure to check out these activities in Montepulciano.

✔️ Visit a winery.

Montepulciano is not only known for its charming landscape and architecture. It’s also hailed as one of the best winemaking regions in the world . Their vino nobile is actually globally renowned. It’s a fine red wine made with grapes sourced from the local vineyards surrounding the town. 

✔️ Stroll along Piazza Grande.

This is the main square in Montepulciano and is a great location for a relaxing stroll. Within it are important buildings and historical landmarks, such as the Town Hall, Contucci Palace, and Palazzo dei Capitani del Popolo.

You can also find the Well of the Grifi and the Lions and the Cathedral of Saint Mary of the Assumption in Piazza Grande. The cathedral is in prime real estate but may not be as attractive as those in Siena and Lucca. 

✔️ Look at scenic views from the clock tower in Palazzo Comunale.

You can climb the 150 steps to the top of the clock tower and have better views of Montepulciano. If you don’t want to take the stairs, you can ride the elevator instead. Although there are still 52 steps left from the elevator stop before you reach the top.

Where to Stay in Montepulciano

It’s really nice to stay in Montepulciano so that you can experience the village without all the daytrip crowds. We ended up visiting Montepulciano in the evening, which was after all the day-trippers had left!

Some of the most highly rated options are Villa Nottola and Hotel Panoramic Montepulciano .

8. San Gimignano

San Gimignano is one of the more famous hilltowns in Tuscany and is enclosed by 13th-century walls. It’s located southwest of Florence and is mostly known for its 14 medieval towers, which gained it the nickname ‘Town of Fine Towers’ .

The town also boasts a 12th-century church ( Duomo di San Gimignano ), a triangular historical square ( Piazza della Cisterna ), and masterpieces of 14th- and 15th-century Italian art, to name a few.

The famous medieval towers are originally built by patrician families who used to control the town. There were 72 of these tower houses, but only 14 have survived after wars and other catastrophes.

Climbing to one of these towers is among the best things you can do in San Gimignano. The town also has a lot of charming shops and restaurants that you can visit in between touring the various historical sights.

How to Get to San Gimignano

To get to San Gimignano, you can take the train, bus, or car. Just keep in mind that there are no train stations in San Gimignano so you’ll have to transfer from a train to a bus to reach the town.

How to Get to San Gimignano by Public Transportation

The nearest train station to San Gimignano is in Poggibonsi . So if you took the train from Florence or Siena, you’ll have to get off at Poggibonsi and take the bus 130 to San Gimignano.

If you want to skip riding the train altogether, there’s always a bus going to San Gimignano from Florence, Siena, and other nearby towns. 

➡️ From Florence , you’ll have to catch bus 131 to Poggibonsi. Once you’re in Poggibonsi, you need to transfer to the #130 bus to reach San Gimignano.

➡️ From Siena , you need to ride the 130A bus. You may need to change buses in Poggibonsi but some of these buses continue to San Gimignano directly.

One thing you need to consider if you want to take the bus is that sometimes, buses don’t arrive on time. You may even have to wait for about an hour.

How to Get to San Gimignano by Car

If you’re driving a car to San Gimignano, the following is the approximate traveling distance from nearby locations:

➡️ Florence : 60 km (1.25 hours)

➡️ Lucca : 90 km (1.5 hours)

➡️ Montalcino : 80 km (1.5 hours)

➡️ Siena : 41 km (45 minutes)

➡️ Pisa : 78 km (1.5 hours)

➡️ Volterra : 30 km (40 minutes)

Driving a car to San Gimignano can give you a much better experience. However, parking can be costly but should be worth it for the convenience of allowing you to leave whenever you want to.

The cheapest parking space is at P1 Giubileo . The rate is only €1.50 every hour and a maximum of €5.00 for an entire day. Subsequent days will be subject to a discount.

P2 Montemaggio, P3 Bagnaia Superiore , and P4 Bagnaia Inferiore have rates that start from about €2.50 per hour and €10.00 for an entire day.

💡 NOTE:   P1 is the cheapest parking area but also the farthest from the center of San Gimignano.

Things to Do in San Gimignano

Here are a few things to do in San Gimignano.

✔️ Climb the tallest tower in San Gimignano .

Torre Grossa is the highest tower in town. It’s also called fat tower by some. You can see a much better view of San Gimignano if you climb to the top of this tower.

✔️ Rent one of the 14 famous medieval towers.

Torre Salvucci Maggiore is available for tours. You can even rent it and have a remarkable place to stay as you tour the rest of San Gimignano and nearby towns in Tuscany.

✔️ Explore the historic center of San Gimignano .

There are several piazzas in the historic center of San Gimignano, which has been declared a UNESCO World Heritage Site since 1990 .

Here you’ll find several small cafes, boutique shops, and Torture Museums. Many restaurants also offer the town’s famous white wine: Vernaccia di San Gimignano .

You also wouldn’t want to miss Duomo of San Gimignano. This cathedral features frescoes that showcase the stories from both the Old and New Testaments.

✔️ Discover the famous Gelateria Dondoli .

If you love ice cream, or you simply want to know why this place is so famous, you’ll have to visit Gelateria Dondoli in Piazza della Cisterna.

This gelateria has graced a lot of news articles and attracted numerous celebrities. They won the Ice Cream Championship of 2006/2007 and 2008/2009. And their Gelato Master, Sergio Dondoli, also bagged the Master of Art and Craft award in 2016 .

Their menu includes all traditional flavors while also offering unique ones, including Dolceamaro which comes with aromatic herbs, and Champelmo which is made with pink grapefruit and sparkling wine.

✔️ Food Tours and Cooking Classes

There are some really great food tours and cooking classes in San Gimignano region. Check them out here for ideas and to book . I would also opt for an organic farm when possible!

Where to Stay in San Gimignano

Check out some of the top-rated hotels in San Gimignano, such as Hotel La Cisterna and Leon Bianco .

One of the prettiest towns in Tuscany is Cortona. It’s a small, historic town in the province of Arezzo and lies on the border between Tuscany and Umbria.

Cortona sat atop a hill (600 meters above sea level) and is enclosed with ancient stone walls dating back to the Etruscan and Roman times. It’s also known for its beautiful churches, including the Basilica di Santa Margherita , and panoramic views of Val di Chiana (Chiana Valley) and Lake Trasimeno.

Cortona is also considered the main cultural and artistic center of the Val di Chiana . And while its international fame only skyrocketed when it became the set of the movie ‘Under the Tuscan Sun,’ the town has always offered lots of amazing places and fun things to do for locals and tourists alike!

How to Get to Cortona

Depending on your budget and desired level of convenience and comfort, you can reach Cortona via train, bus, and car.

How to Get to Cortona from the Airport

If you’re going to Cortona by plane, you’ll be landing at either of the following closest airports to Cortona:

➡️ Perugia Sant’Egidio International Airport 

➡️ Florence Peretola International Airport 

➡️ Pisa International Airport  

➡️ Rome Fiumicino International Airport 

From the airport, you can then ride a taxi, bus, or train.

How to Get to Cortona by Train

You can reach Cortona by train from Rome, Florence, and Venice.

➡️ From Rome

You can pick between a slow or a fast train.

The slow train will take about 2 hours and 25 minutes before stopping at the Camucia-Cortona station.

The fast train only takes 1 hour and 45 minutes but will only stop at Terontola train station which is still 10 km from Cortona.

From the station, you’ll need to ride a taxi or a local bus .

➡️ From Venice

You can ride the fast train Freccia Rossa or Italo Train to Florence, which would take about 2 hours. And when you reach Florence, there’s a local train that will stop at Camucia-Cortona station and only takes 1 hour and 20 minutes. 

How to Get to Cortona by Bus

The Camucia-Cortona and Terontola rail stations are both connected to bus services. You will ride the bus up the hill and stop just outside the center at Piazza Garibaldi. You can also ride a bus to Cortona from nearby towns and villages in Tuscany.

How to Get to Cortona by Car

If you’re traveling from Rome or Florence, you can drive through the main highway A! Superstrada del Sole and exit at the sign “Bettolle”. You will then have to take the second exit, “Cortona San Lorenzo”.

Afterward, you just have to follow the road signs to Cortona until the hill appears in about 5 minutes. 

Things to Do in Cortona

Add these things to do in Cortona to your list while visiting this charming Tuscan town.

✔️ Visit the Museum of the Etruscan Civilization (MUSEO DELL’ACCADEMIA ETRUSCA (MAEC))

✔️ Shop along the side street of Cortona

✔️ Explore Cortona on foot through Via Nazionale 

✔️ Go sightseeing at Belvedere di Cortona

✔️ Enjoy a delicious gelato

✔️ Visit the Diocesan Museum

✔️ Visit this cute shop for a wine tasting

Where to Stay in Cortona

Definitely check out Hotel San Luca or Villa Schiatti .

10. Suvereto

If you’re looking for charming villages in Tuscany, Suvereto is another medieval town that should go on your list. 

It’s nestled in the province of Livorno, in between the hills and the Etruscan Coast. Within its walls, you can travel back in time to before 1000 as you gaze upon the prominent old architecture and stonework.

From historical buildings to medieval churches and stone houses, structures all around Suvereto create an ancient yet welcoming atmosphere.

Nature also plays a big role in this Tuscan town’s charm. Suvereto is surrounded by chestnut trees, oak trees, and cork trees (Quercus suber)—which is where the town got its name.

How to Get to Suvereto

You can reach Suvereto by bus, train, ferry, or car.

How to Get to Suvereto from the Airport

Nearby airports to Suvereto include:

➡️ Elba Island Airport

➡️ Pisa Airport

➡️ Florence Airport

➡️ Rome Airport

From the airport, you can ride a bus or train to reach Suvereto.

How to Get to Suvereto by Car

➡️ If you’re from the north , you’ll need to take the A12 Genova-Livorno-Rosignano Marittimo motorway before exiting at Rosignano Marittimo. You’ll then continue to the SS 1 highway and follow the direction for Venturina-Piombino-Elba.

Continue to follow the directions for direction for Venturina-Campiglia Marittima until you reach SS 398, which will take you up to Suvereto.

➡️ If you’re traveling from the south , take the A12 motorway to Civitavecchia then continue on the SS 1 Aurelia to Grosseto. Then follow the directions to Venturina – Piombino – Elba Island then to Campiglia Marittima before taking the SS 398 until you reach Suvereto.

Things to Do in Suvereto

✔️ Explore Museo di Arte Sacra “San Giusto” (Museum of Sacred Art of Suvereto)

✔️ See the 14th-century depiction of Madonna con Bambino at the Chiesa della Madonna di sopra la Porta.

✔️ Tour the inside of the 13th-century palace: Palazzo Comunale.

✔️ Discover the collection of dolls from various eras in the Museo della Bambola.

✔️ Get close to the Romanesque architecture of Pieve di San Giusto.

Where to Stay in Suvereto

Some of the best accommodations in Suvereto include Borgo al Cielo – Albergo Diffuso and Agriturismo Biologico Bulichella .

Barga is a charming town in northwestern Italy, located in the province of Lucca. It’s set on top of the Tuscan-Apennine hills (410 meters above sea level) right in the heart of the Serchio Valley.

Aside from being a beautiful home to around 10,000 people, Barga is also a worthwhile tourist destination. It offers a picturesque view of nature, medieval architecture, tons of outdoor activities, and a dynamic music scene.

Barga is widely recognized in the tourism industry. It bagged several awards, including “One of the Most Beautiful Villages in Italy,” and merits from “Orange Flag Touring Club” and “Cittaslow”. 

How to Get to Barga

You can reach Barga by train, bus, or car.

How to Get to Barga from the Airport

There are five airports closest to Barga:

➡️ Milan Airport

➡️ Verona Airport

➡️ Bologna Airport

From the airport, you can either ride a bus or a train to Barga.

How to Get Barga by Train

You can only ride trains heading to Barga from Lucca and Pisa Centrale stations .

There are more frequent trains from Lucca and will take you on a direct 40-50-minute ride to Barga. 

If you’re leaving from Pisa Centrale, you’ll most likely need to stop at Lucca to change trains. There are only about 5 trains every weekday that go directly to Barga from Pisa Centrale station.

How to Get to Barga by Bus

Buses to Barga mostly leave from Lucca and will take about an hour. And if you’re already in the Garfagnana area, you can catch a bus from Pieve Fosciana, Castelnuovo, and Castelvecchio.

How to Get to Barga by Car

➡️ From the South

Take Highway A1 towards A11 before heading to the Capannori exit. From there, follow indications to SS 439 towards Lucca-Borgo a Mozzano-Fornaci di Barga. You’ll then have to follow the signs to Barga on SS 445. 

➡️ From the North

Take Highway A1 following the signs to Genova-Livorno, Viareggio, and to Lucca. You’ll need to exit at Lucca est and follow the indications to Borgo a Mozzano and Fornaci di Barga before taking the SS 445 to Barga.

Things to Do in Barga

✔️ Visit the Romanesque-style Cathedral of San Cristofano.

✔️ Explore in the Museo Civico del Territorio.

✔️ Stroll along the main square of the center: Piazza del Comune

✔️ Visit and learn more about the historic Teatro dei Differenti.

✔️ Admire the 16th-century complex of Santa Elisabetta Church.

Where to Stay in Barga

For some great options to stay in Barga, check out Il Ciocco Hotels and Villa Gherardi – B&B e Hostel .

12. Monteriggioni

Monteriggioni is another one of the walled medieval towns in Tuscany with well-preserved walls, a castle, and defense towers. It lies on the hill of Monte Ala in the province of Siena, where its imposing towers have stood since the beginning of 1200.

💡 FUN FACT:   The towers are so impressive that Dante Alighieri referred to them as “horrific giants” in his Divine Comedy.

Without a doubt, Monteriggioni has retained its Medieval character, which makes for this circular town’s main charm. But aside from its historic structure, Monteriggioni is also highly regarded for its vast vineyards and several excursion destinations. 

How to Get to Monteriggioni

You can reach Monteriggioni by bus or car. Unfortunately, there are no train stations in town. The closest railway station is Castellina in Chianti-Monteriggioni, which is still 3km from Monteriggioni.

How to Get to Monteriggioni from the Airport

There are five closest airports to Monteriggioni:

➡️ Bastia Airport

➡️ Forli Airport

From the airport, you can reach Monteriggioni by riding a train. However, if you’re leaving from Pisa, you’ll have to transfer to a bus before reaching Monteriggioni.

How to Get to Monteriggioni by Bus

You can ride a bus to Monteriggioni from the nearby cities, including Florence, Pisa, and Volterra. Bus stops near the castle of Monteriggioni are the Rotonda (main bus stop) and Scuola.

Both stops are about 500 meters from the castle.

How to Get to Monteriggioni by Car

Traveling by car to Monteriggioni is the more convenient option since you’ll have control over your time. However, keep in mind that vehicles are prohibited inside the town proper . You will have to leave your car at either of the several parking lots outside of Monteriggioni.

💡 NOTE:   All parking spaces require a small fee.

You can get here by car via the Florence-Siena dual-carriageway. You need to take the “Monteriggioni” exit 10km from Siena (the city) and simply follow the directions toward the town.

Here’s the approximate distance and driving duration from several nearby destinations:

➡️ Siena – 21 km (20 minutes)

➡️ Florence – 65 km (1 hour)

➡️ San Gimignano – 28 km (50 minutes)

➡️ Volterra – 40 km (50 minutes)

Things to Do in Monteriggioni

✔️ Taste the traditional red wine of Monteriggioni: Chianti Colli Senesi Monteriggioni

✔️ Visit in July and take part in their famous Medieval Festival.

✔️ Try on some ancient armor and swing a 10kg sword at the Museo delle Armature (Museum of Arms – Monteriggioni in Arms).

✔️ Visit the tiny 13th-century Church of Santa Maria Assunta.

✔️ Enjoy great food and drinks at the heart of Monteriggione: Piazza Roma

Where to Stay in Monteriggioni

Borgo San Luigi and Il Piccolo Castello are great choices of accommodations in Monteriggioni.

13. Fosdinovo

Another small town in Tuscany that is worth visiting is Fosdinovo. It’s located in northern Tuscany just 45 miles north of Pisa. It lies within the drainage basin of Val di Magra and is considered the gateway to the historic Lunigiana region.

Although this town is not a staple in every tourist’s itinerary, I know you won’t be disappointed. It boasts a perfectly preserved castle-fortress and a scenic view of the sea and mountains.

The town is also close to the Apennine and the Apuan Alps. So contrary to the rolling hills that you can find in southern Tuscany, steep hills will meet you in Fosdinovo. Winter may also bring snow to this small village.

How to Get to Fosdinovo

You can reach Fosdinovo by train, bus, or car.

How to Get to Fosdinovo from the Airport

Included in the airports closest to Fosdinovo are Pisa Airport and Florence Airport .

From either airport, you can either ride a bus or train to go to Fosdinovo. Riding a taxi is also another option if you’re leaving from Pisa Airport.

How to Get to Fosdinovo via Public Transport

The closest railway station to Fosdinovo is Sarzana. From there, you’ll need to ride a CTT bus to reach Fosdinovo.

How to Get to Fosdinovo by Car

You’ll need to drive via the A12 motorway and take the Sarzana exit. Continue driving on the Aurelia state road towards Carrara until you reach the crossroads for Fosdinovo. You’ll then need to climb for about 6 km before you reach Fosdinovo.

Things to Do in Fosdinovo

✔️ Explore the town’s main attraction: Malaspina Castle.

✔️ Visit the marble tomb of Galeotto Malaspina in the Church of San Remigio

✔️ Admire the 15th-century wooden statue of the Virgin Mary in the Compagnia dei Bianchi Oratory

✔️ Stroll along the beautiful park in Villa Malaspina

✔️ Learn more about the resistance in the Apuan and Luni areas in the Audiovisual Museum of the 2nd World War Resistance.

Where to Stay in Fosdinovo

Both Castello Malaspina di Fosdinovo and Locanda De Banchieri are highly rated by hundreds of travelers as some of the best hotels in Fosdinovo.

14. Volterra

Volterra is a hilltop Etruscan town in Tuscany. It’s located in the province of Pisa and attracts countless tourists for its archeological sites, museums, excursion destinations, and overall picturesque landscape. 

The town’s Etruscan heritage is still evident to this day, especially with the protective walls that have surrounded the town since the 5th to 4th centuries BC.

Volterra is also filled with boutiques and handicraft workshops where you can choose from a wide range of souvenirs. Included in your choice are alabaster handmade objects for which Volterra is highly regarded.

💡 FUN FACT:   Volterra is dubbed “the city of Alabaster” for their world-famous work with Alabaster. This ancient tradition originated from the Etruscans.

Tip : Use their Volterra Card so you can save money on most entrance fees to the town’s several attractions.

How to Get to Volterra

You can reach Volterra via train, bus, or car. You also have the option of riding a taxi if you’re leaving from an airport.

How to Get to Volterra from the Airport

There are five airports near Volterra:

From there, you’ll need to ride a train before transferring to a bus or taxi. However, if you’re leaving from Bastia Airport, you’ll need to ride a ferry and then a bus (or drive) before reaching Volterra.

How to Get to Volterra by Car

Volterra is not too far from the surrounding cities and you can definitely drive there. However, you need to keep in mind that the last kilometers before reaching the town proper might be a tad difficult since the road is very curvy and goes uphill.

If you’re leaving from Florence, you need to take the Firenze-Siena roadway before taking the exit at Colle di Val d’Elsa Nord. You’ll then have to follow the road signs toward SR68 and Volterra.

How to Get to Volterra by Bus

You can take a bus to Volterra from Pisa, Siena, and Florence. However, there are no direct routes and you’ll have to change buses before getting to Volterra. 

If you’re at the Volterra Saline-Pomerance train station, take the bus line 780 which is only about a 20-minute ride to Volterra.

How to Get to Volterra by Train

The Cecina-Volterra railway line is the closest train station to Volterra. You’ll have to get off at the Volterra Saline – Pomarance stop, which is still 10km away from the city center of Volterra. However, this line is small so check the train schedules beforehand.

There are larger railway stations that are still close by as well. These are in Cecina and Pontedera.

Things to Do in Volterra

✔️ Taste some delicious Italian delicacies during Volterra’s Saturday market.

✔️ Climb the tower of Palazzo dei Priori to better enjoy the town’s view.

✔️ Stroll along and relax in the town’s main square: Piazza dei Priori

✔️ Pass through the Porta dell’Arco, the oldest gate in Volterra.

✔️ Explore the Museo Etrusco Guarnacci (Etruscan Museum)

Where to Stay in Volterra

Check out Albergo Etruria and Hotel La Locanda for your hotel stay in Voleterra!

Pienza is a small town perched on top of a beautiful hill in the province of Siena. The town offers magnificent views of Val d’Orcia, encompassing expansive vineyards, rolling hills, charming villas, and rows of cypress trees. 

Aside from its natural landscape, Pienza is also famous for its pecorino cheese, historic buildings, and romantic street names. This Renaissance town is known as a legacy of Enea Silvio Piccolomini (Pope Pius II) as well.

Pope Pius II redesigned the town to embody his idea of the ‘ideal city’ with respect to his Humanist vision and philosophy. He tasked architect Bernard Rossellino and the great humanist Leon Battista Alberti to lead the construction project.

After 3 years, they have successfully built the Piazza Centrale, Pienza Cathedral, the Papal Residence, and the Municipal Palazzo, among others. Palazzo Piccolomini is what Pope Pius II chose as his summer residence.

After the redesign, the town, which is previously called Corsignano, was renamed Pienza, which translates to ‘city of Pius’. In 1996, Pienza was officially recognized as a UNESCO World Heritage Site.

How to Get to Pienza

Depending on where you’re traveling from or your personal preferences when it comes to comfort and convenience, you can get to Pienza by car or bus. You might also have to ride a train to a nearby town and then transfer to a local bus since there is no train service in Pienza.

How to Get to Pienza by Car

Pienza is between San Quirico d’Orcia and Montepulciano on SS146. Going there by car is the easiest , in my opinion. You won’t have to rely on bus schedules which can leave you waiting for a long time.

➡️ If you’re from Montepulciano , you can take the road to Torrenieri and SS2. Then, take the SS2 south to San Quirico d’Orcia. You can then find the SS146 which runs east to Pienza.

➡️ If you’re from Siena , you need to take SS2 south to SS146. But if you prefer a more scenic route, you can take SS438 south through Asciano and via Monte Oliveto Maggiore.

➡️ If you’re from Florence , the quicker route is taking the A1 Autostrada and EXIT Valdichiana. This will only take about an hour and 40 minutes. Although this can change depending on the traffic. For a more scenic route, your option is to take the FI-SI (Raccordo Autostradale Firenze-Siena) and EXIT Siena Sud. This can add 20 more minutes to your traveling time.

➡️ If you’re from Rome , take A1 Autostrada and EXIT Chiusi-Chianciano Terme. Depending on the traffic, you can reach Pienza between 2 hours and 3.5 hours.

How to Get to Pienza by Bus

If you don’t want to drive a car, there’s always the option of taking the bus. A bus service between Chiusi train station and Montepulciano can bring you to Pienza. You can also catch a bus from Siena.

💡 NOTE:   It’s important to study the bus schedules in order to save some time waiting for a bus to arrive. Also, there’s only a limited bus service running on Sundays and public holidays.

➡️ If you’re from Florence , you’ll need to go on a bus to Siena, which could take about 3-4 hours. From Siena, you’ll have to change buses at least once to reach Pienza. 

➡️ If you’re from Rome , the entire bus ride to Pienza can take at least 5 hours. You can ride the FlixBus to Siena and then transfer to a local bus to reach Pienza.

Things to Do in Pienza

Pienza is such a small town that I would still recommend visiting it even if you only plan a short visit to Tuscany.

✔️ Visit the previous summer residence of Pope Pius II: Palazzo Piccolomini

Just beside Pienza Duomo, you can see the very walls wherein Pope Pius II resided during summer. There are guided tours for Palazzo Piccolomini that happen at regular intervals during the day. The tours come with a host and an audioguide, and usually last for about 40 minutes.

You will be guided through the different rooms inside the palace. The audio guide will then offer an explanation in your chosen language and in your own time. The tour also includes rooms that can be interesting for kids as well, such as the armor room and the Pope’s bedroom.

To culminate the tour, you will be brought to the amazing suspended garden in Palazzo Piccolomini. This will allow you to bask in the vast stunning views of the countryside. The garden’s strategic location is intentional, placing it at the heart of the vision of the Pope’s ideal town.

✔️ Taste the pecorino cheese that Pienza is famous for.

Pienza is especially proud of its pecorino cheese—and rightfully so!

This cheese is made from sheep’s milk and comes in many varieties. The two main varieties are:

🧀 Red Rind Cheese seasoned with Tomato Juice

🧀 Black Rind Cheese (aged pecorino)

If you want to try some, you can easily find pecorino cheese in the shops all over Pieanza. I recommend trying it alongside some cured meats and a glass of their local wine too! Pasta dishes are often made with the famous cheese as well. 

💡 FUN FACT:   Pienza celebrates ‘Fiera del Cacio’ in September. This is a folkloric event where local producers can test their skills at making cacio wheels roll around a wooden pole. This event is held at Pienza’s main square.

✔️ Stroll along Piazza Pio II

Piazza Pio II is the town’s main square and was named after Pope Pius II. It has a unique trapezoidal shape and is dotted with several important structures, like the cathedral, Palazzo Borgia, Palazzo Piccolomini, and an ancient well called ‘pozzo dei cani’ or dog’s well. 

You can find it relaxing to simply stroll through the square and admire the 15th-century buildings. Or if you happen to visit during summer, you might catch one or two concerts being held here.

💡 NOTE:   Piazza Pio II is car-free. So if you’re driving a car, you have to park at some of the designated parking spaces before coming here.

✔️ Visit Pienza Cathedral and explore the crypt below it 

Cattedrale dell’Assunta is Pienza’s cathedral and is located in Piazza Pio II. It was built in the 15th century by architect Bernardo Rossellino. The architecture of the building is a reflection of the Renaissance style and some Gothic influences that Pope Pius II saw and liked during his travels.

And after you’ve admired the cathedral’s structure, I recommend exploring the crypt and labyrinth below it. 

The crypt is the San Giovanni church that preserved the baptismal font designed by Bernardo Rossellino. You can see many Flemish tapestries within the crypt, as well as the medieval Santa Maria church.

A little beyond the crypt is the labyrinth: a maze of narrow brick tunnels. Visiting both the crypt and labyrinth can take between 15 and 30 minutes. But unlike in Montepulciano, there are no caves. So I only suggest visiting if you simply want to see the entirety of the cathedral and the church of Santa Maria.

💡 NOTE:   The cathedral is closed on Tuesdays and visiting hours vary depending on the day and season. It’s best to check their official website prior to visiting.

Where to Stay in Pienza

Relais Il Chiostro Di Pienza and Borgo Sant’Ambrogio – Resort are a couple of highly recommended places to stay in Pienza.

Arezzo is technically a city, not a town. But it’s always worth a visit so I wouldn’t leave it out my list.

Arezzo is known as the city of gold and high fashion . Many known artists and poets are from Arezzo, including Giorgio Vasari, Guido of Arezzo, and Guittone d’Arezzo. The Renaissance artist Michelangelo also hailed from the province of Arezzo.

The city is filled with amazing frescoes and sculptures, most of which you can find in churches. Some of the more popular artworks are the painted vaulted ceilings and the 15th-century fresco of Mary Magdalene made by Piero della Francesca in the Arezzo Cathedral. 

The Basilica di San Frances also has a chapel that is adorned with more of Piero’s stunning frescoes. And in Basilica di San Domenico , you can find the 13th-century painting ‘Crucifix’ by Cimabue. 

Aside from art and history lovers, shopping fans will also find Arezzo worth visiting. From trendy clothes and elegant jewelry to household goods and antiques, you can find all kinds of items you’ll want for a shopping spree!

How to Get to Arezzo

In order to get to Arezzo, you can either take the train, ride a bus, or drive a car. For convenience, I always opt for driving a car and suggest you do the same as well.

How to Get to Arezzo by Car

You can easily reach Arezzo by taking the Autostrada del Sole (A1 Milan-Naples). You will then take the exit at the tollgate of Arezzo and travel for about 11km more to reach the city center.

➡️ If you’re from Siena , you first need to take the SS73. This connects to Autostrada di Sole where you’ll then go north before exiting at Arezzo.

But if you want a more scenic alternative to this route, you can always take the exit at Colonna di Grillo and head toward Chianti before reaching Arezzo. Or you can take the exit at Rigomagno and stop at Lucignano before you can reach Arezzo.

How to Get to Arezzo by Train

If you don’t want to drive, traveling to Arezzo by train is also fairly easy. The train station of Arezzo is located along the Bologna-Rome railway line. Trains from Rome, Florence, and other places in Italy frequently run to Arezzo too, so you probably won’t have a very difficult time waiting.

Things to Do in Arezzo

Although Arezzo is out of the way from the more famous tourist spots in Tuscany, this charming city has so much to offer. Whether you’re a solo traveler or you have your family with you, you can find a lot of fun things to do in Arezzo.

✔️ Watch a historical reenactment

If you happen to visit Arezzo on the third Saturday of June and the first Sunday of September, I recommend watching the reenactment of the Saracen Joust held in Piazza Grande. But if your visit doesn’t coincide with these dates, you can still learn about Saracen Joust at the Saracen Jousting Museum.

✔️ Admire the beauty of the Palace of Fraternita dei Laici

This palace is a gorgeous building that you can find in Piazza Grande, the main square of Arezzo. The structure itself is already noteworthy so if you’re in a rush, you can just admire it from the outside.

It’s amazing to see the sculptures of Bernardo Rossellino (the Madonna della Misericordia) and the statues of Pope Blessed Gregory X and St. Donald placed artfully outside of the palace. You can also see one of the oldest functioning clocks in Italy on top of this building.

If you have a bit more time, I suggest going in, especially if you’re fascinated by the arts. Inside the palace is the Museum of Fraternita, which holds a vast collection of 6000 paintings, sculptures, and antique furnishings.

💡 NOTE:   There is a small entrance fee to the museum.

✔️ Go shopping!

After visiting museums and witnessing historical artworks, you can enjoy yourself more and indulge in some shopping. One good place to do this is Corso Italia, a pedestrian street that’s always bustling with activity. There are a lot of boutiques, antique shops, cafes, and restaurants on this street. 

And if you particularly want a plethora of choices when it comes to antiques and other items, I recommend visiting Arezzo on the first Sunday of every month.

During this day, the festive vibe in the city is magnified as approximately 400 stalls open up in Piazza Grande and the surrounding streets. You can find various artwork, furniture, clothing, home goods, toys, and jewelry.

Where to Stay in Arezzo

When looking for places to stay in Arezzo, check out B&B Hotel Arezzo and Hotel Minerva .

17. Pitigliano

Pitigliano is a small town in the Maremma region that was built on a tuff cliff. It’s located on a ridge about 300 meters above sea level and is surrounded by panoramic green valleys. With scenic views and rich history, Pitigliano is one of the best spots in Southern Tuscany.

💡 FUN FACT:   An ancient legend credits two Romans in the name of Petilio and Celiano for the foundation of Pitigliano. And it is by combining their names that the town got its own name.

Due to its interesting location, it became a unique-looking walled town whose main attractions include its medieval stone streets, museums, and the Jewish quarter.

Ptigliano is actually well known for its nickname ‘Little Jerusalem’ . This is because when the Jews were escaping, this town became their refuge in the 14th century. And as their number grew, they built a temple in Pitigliano in 1598.

When the 17th century came, Medici annexed Pitigliano which led to the Jews being confined in ‘ghettos.’ Fortunately, the local government understood the Jews’ vital role in the town’s economic and commercial activities and they worked on improving their status and fundamental rights.

How to Get to Pitigliano

You can get to Pitigliano by car, bus, or train. However, if you’re taking the train, you still need to transfer to a bus in order to reach Pitigliano. There is no train station within the town itself.

How to Get to Pitigliano by Car

Driving a car to get to Pitigliano (and to go around Tuscany) is the best option for me.

You need to take the A1 motorway heading to Rome and get off at Orvieto. You then need to take SS71 towards Bolsena, then SS2 Cassia, and SS74 which heads toward Pitigliano.

You have to drive through Grande Raccolto Anulare towards Florence. Once you reach Rome, take the A1 highway, turn at Orte, and follow the signs for Viterbo. You just then have to take SS71 until you reach Pitigliano.

➡️ If you’re heading in from Rome , you will have to take the Roma-Civitavecchia motorway and follow the signs for Grosseto-Livorno. You then need to take the exit at Albinia and follow the signs for Manciano. Simply follow the signs for Pitigliano afterward.

How to Get to Pitigliano by Bus

If you don’t feel like driving, there are daily buses that run to Pitigliano from Siena, Florence, and Grosseto.

How to Get to Pitigliano by Train

While you can’t ride a train straight to Pitigliano, you can still take it and stop at any of the following nearby railway stations:

➡️ Grosseto (80km from Pitigliano)

➡️ Albinia (50km from Pitigliano)

➡️ Orbetello (57km from Pitigliano)

➡️ Viterbo (57km from Pitigliano)

From these stations, you can catch a bus that will take you to Pitigliano.

Things to Do in Pitigliano

✔️ Explore the Jewish Quarter

The Jewish synagogue and the museum beside it are worth visiting. The museum will give you an idea of how the Jewish community has lived their daily lives. You can also see the Mikveh, which is a Jewish ritual bath where it’s believed to help people achieve purity. There’s also a butcher shop and bakery called Forno delle Azzime.

✔️ Visit Fontana Delle Sette Cannelle

If you want some nice views, I suggest visiting Fontana delle Sette Cannelle or Fountain of the Seven Spouts in English. It was built in 1545 in Piazza della Repubblica and gives you access to its surrounding magnificent views.

The fountain has seven pipes, as its name suggests, which are each decorated with a sculptured animal head. You can also see some arches that are actually an aqueduct leading to the fountain. These arches were built in the 1600s by Antonio da San Gallo il Giovane in order to supply water to the region, as instructed by the Medici family.

✔ Wander within Palazzo Orsini

If you go to Palazzo Orsini, what you’ll see is an impressive building with high crenelated walls and defensive towers. All of which are the result of several renovations starting from the Middle Ages until the 19th century.

The palace was originally used as a convent but was transformed into a fortress in the mid-13th century by the Aldobrandeschi. Around the middle of the 16th century, this fortress was significantly restructured under the dominion of the Orsini. A transformation was also done during the Lorraine period between 1777 and 1840.

Aside from its noteworthy architecture, the palace also features two museums: Museo di Palazzo Orsini and Museo Civico Archeologico di Pitigliano.

Museo di Palazzo Orsini

This gorgeous museum holds sacred art and liturgical furnishings from the Cathedral of Pitigliano and other surrounding churches.

There are 18 rooms in the entire museum, featuring some famous art pieces like the wooden statue of Madonna and Child by Jacopo della Quercia and the panel Madonna and Child with angels and saints Francesco and Pietro made by Guidoccio Cozzarelli.

Museo Civico Archeologico

This museum serves not only as a gallery but also as a restoration workshop and warehouse. It houses numerous finds from the excavations of the Poggio Buco necropolis and from the finds in Pitigliano. These pieces date back to the Etruscan era.

Where to Stay in Pitigliano

And if you’re looking for something that many other travelers confidently recommend, FicOlivo and B&B Locanda Il Tufo Rosa are two of the many accommodations with a lot of glowing reviews.

18. Monticchiello

Another hill town in Tuscany that is worth visiting is Monticchiello. It’s a small medieval village that is not often included in many traveler’s itineraries but somewhere I still recommend for you stop by. It has definitely a lot to offer not only in sights but also in culture.

Monticchiello is nearby other more famous destinations, like Siena, Pienza, and Montepulciano. It is only a small town but it boasts a stunning natural beauty and a unique theater tradition that distinguishes it from other Tuscan towns.

The town’s famous ‘poor theater’ or ‘Teatro Povero’ offers a theatrical experience that characterizes Monticchiello and its locals. It showcases the day-to-day life in the village, inspired by their local history and re-introducing the customs of rural civilization.

How to Get to Monticchiello

Despite being not as popular as some of the best towns in Tuscany, Monticchiello is easy to reach. You can drive there or opt for public transportation, which consists of a train and bus.

How to Get to Monticchiello by Car

As always, I believe driving is the easiest way to get to Monticchiello. You just have to take the A1 motorway and exit at the Chiusi-Chianciano Terme junction. About 20km ahead of it is the town of Monticchiello.

➡️ From Florence

Take north A1 then exit at Valdichiana. You then have to continue on SP327 toward Torrita di Siena, followed by SP135 and SP17 to Montepulciano. Then simply head towards Monticchiello until the SP88 turn.

How to Get to Monticchiello by Public Transportation

You can take a train and stop at the Chiusi-Chianciano Terme train station. From Chiusi-Chianciano, you can catch a bus to Monticchiello which could take about 2 hours and 10 minutes.

There are also available taxis there. Or if you want, you can drive a car from Chiusi-Chianciano to Monticchiello.

Things to Do in Monticchiello

✔ Catch one of their unique theater performances.

Every summer, there are open-air theater performances in Monticchiello. If you happen to visit during this time, I highly recommend not missing the chance to see it!

This form of theater was first introduced in Monticchiello as a community project. It was 1967 and their community was going through significant changes. The theater then became their way of expressing various thoughts and fears about the said changes.

Over the years, their ‘poor theater’ performances have broached several topics that not only concern the local community but also touch international interests.

✔ Visit the church of Saints Leonardo and Cristoforo

Pieve dei Santi Leonardo e Cristoforo was built in the second half of the 13th century with a Gothic architectural style. Its simple facade has a beautiful rose window above an ogival portal.

The interior was remodeled in the 18th century and has walls that feature many frescoes from the Sienese school. These frescoes date back to the 14th and 15th centuries.

✔ Look for the traitor’s head!

A fun challenge for anyone visiting Monticchiello is to look for the traitor’s head that was oppressed by a cannonball. Hint: It’s on the facade of one of the houses in the village streets, about 5 meters high.

This piece of art was made in the 14th century to depict the traitor who opened the city gates for the Florentine enemies in exchange for two thousand guilders.

Where to Stay in Monticchiello

These two farmhouses having glowing reviews: Agriturismo Riposati and Agriturismo Barbi.

19. Montalcino

In the province of Siena, Tuscany, you will find the interesting hill town called Montalcino. It overlooks expansive Sangiovese vineyards and offers a scenic view of Val d’Orcia. 

Montalcino gained worldwide recognition mainly for its two famous wines: Rosso di Montalcino and, of course, Brunello di Montalcino . But even if you’re not a wine enthusiast, there is still a lot in this town that can make your visit worthwhile!

The town can also interest art lovers with its museums and architectural masterpieces. Among its notable sites are the Rocca (a fortress built in 1361) and the tall clock tower. There are also several arts and crafts shops where you can stop by.

How to Get to Montalcino

There are three ways to get to Montalcino: by train, bus, and car.

How to Get to Montalcino by Car

You need to drive about 8km off the SS2 via Cassia. This road runs between Rome and Siena. 

You can easily find a rental car in Siena or Florence. And if you don’t like driving throughout your vacation, there are private drivers that you can hire as well.

How to Get to Montalcino by Public Transport (Train + Bus)

There are numerous trains that run on the Grosseto line every day. The nearest stop is at Buonconventio which is still about 14km from Montalcino. From there, you can catch a bus to Montalcino which can take about 30 minutes.

You can also ride a bus from Siena, although you have to change buses once in Buonconvento.

Things to Do in Montalcino

✔ Try Montalicino wine!

Being known for its world-class wines, especially the Brunello, it’s almost a crime not to go wine tasting in Montalcino. You simply have to taste for yourself why their wines are highly praised.

You can find a lot of ‘enotecas’ or wine repositories that offer wine tasting. And if you liked them, you can buy your favorite bottle or two. Most of the wines that they offer for wine tasting are the town’s two biggest sellers, Brunello and Rosso di Montalcino.

Brunello di Montalcino is made from 100% Sangiovese grapes and is aged for 5 years. 2 of these aging years are spent in oak barrels. Brunello can then be released for public consumption on January 1st the fifth year after harvesting.

Rosso di Montalcino is a wine made from 100% Sangiovese grapes as well. The only difference is that the aging duration is not as strict as Brunello’s. Rosso can be released to the market after only a year of aging.

✔ Explore the fortress

The Rocca or fortress in Montalcino has been dominating the town’s skyline since 1361. It was built by the Sienese to mark the passage of Montalcino under Siena’s power.

The fortress sits on the town’s highest point. And if you climb to the top of the tower, you’ll gain access to an uninterrupted view of the natural beauty of Montalcino and Val d’Orcia. You’re also allowed to walk along the walls, giving you more views of the town from different angles.

There are practically no significant changes in the fortress since the Middle Ages. Its mighty structure is now used as a venue for concerts, festivals, and other community events. And every July in the summer, the Jazz & Wine Festival makes the fortress more inviting for locals and tourists alike.

💡 NOTE:   The fortress courtyard is open to the public for free. However, there is a small fee for climbing the steps to the walls and tower.

Where to Stay in Montalcino

Check out these Montalicino accommodations that are highly rated by hundreds of people: Le Ragnaie and Drogheria e Locanda Franci .

20. San Quirico d’Orcia

San Quirico d’Orcia is one more town in Tuscany that sits prettily on top of a hill. This commune is named after Saint Quiricus and is blessed with a serene natural landscape. The magnificent views in this town include vineyards, olive groves, lovely hills, and lines of cypress trees, to name a few.

History, art, and architecture lovers will also love visiting San Quirico d’Orcia. Here you can see some medieval churches whose structure will make for memorable photographs!

During medieval times, San Quirico d’Orcia was in a strategic location where emperors, pilgrims, and merchants constantly pass through. In fact, Emperor Federico Barbarossa camped here in 1154 and met with the pope’s emissaries to talk about his coronation.

How to Get to San Quirico d’Orcia

It’s easy to get to San Quirico d’Orcia by driving. If you’re from Siena, simply take the SR2 and it will lead you straight to the heart of Val d’Orcia. 

And if you choose to try public transportation, just keep in mind that there are no train services in the actual town. The nearest station is still in Buoconvento. From there, just hop on to a TIEMME bus and you can reach San Quirico d’Orcia.

Things to Do in San Quirico d’Orcia

✔ Walk along Horti Leonini

One of the attractions you shouldn’t miss in this beautiful Tuscany town is Horti Leonini. It’s a Renaissance garden that dates back to 1581. This stunning Italian-style garden is named after Diomede Leoni to whom this land was gifted by Francesco I de’ Medici.

Horti Leonini is located in the main square of San Quirico d’Orcia. It features geometric box hedges, a crumbling stone tower, and manicured green space that makes for a relaxing strolling area.

✔ Admire the Collegiate Church of Saints Quirico and Giuditta

Collegiate Church of Saints Quirico and Giuditta is an admirable Romanesque church built with cream-colored stones. This makes the building even more attractive in daylight, beckoning tourists to look and take photos.

This church is dedicated to Quiricus, a 3rd-century child martyr. And aside from his depiction of the altar, the church design also includes the rare example of Lombard style in Tuscany.

Among the church’s three doorways, one was credited as a masterpiece of Giovanni Pisano. Other remarkable works in the church’s interior include the altarpiece by Sano di Pietro, a 15th-century painter from a Sienese school. 

✔ Celebrate Festa di Barbarossa  

As I mentioned above, Federico Barbarossa camped in San Quirico as he was on the way to his coronation. And in honor of him, the town now celebrates Festa di Barbarossa in June of every year. This fest includes people donning beautiful costumes and participating in period archery tournaments.

Where to Stay in San Quirico d’Orcia

Hotel Palazzuolo and Antica Sosta are great places to stay in San Quirico d’Orcia.

21. Anghiari

Although this is the last in my list of best towns in Tuscany, Anghiari is by no means the least of them. This hill town found in the province of Arezzo is also a charming village that still clearly depicts its medieval roots.

During the Medieval Ages, Anghiari played a vital role in war. The flat valley under it became the place where the famous Battle of Anghiari transpired in the year 1440. This is where the Florentine troops won against the Milano army.

Anghiari is enclosed in massive walls built in the 13th century. To this day, the walls still stood tall, preserving the original atmosphere in this small medieval town.

Anghiari is now considered one of the most beautiful villages in Italy and was awarded an Orange Flag distinction from the Italian Touring Club.

How to Get to Anghiari

To get to Anghiari, you can either drive a car or take public transportation.

If you’re driving from Florence, you just have to take the A1 road towards Arezzo, and then go on E78 or SP43 (Strada Provinciale della Libbia). You will then find Anghiari along E45 by the Sansepolcro exit.

For public transport, I recommend taking the train to Arezzo where you’ll then have to transfer to a bus in order to reach Anghiari.

Things to Do in Anghiari

✔ Explore the museums

The Battle of Anghiari was painted by Leonardo da Vinci to honor the victory and materialized its glory. However, the original artwork was lost. What remained is the copy made by Paul Rubens, which you can find in the Museum of the Battle and Anghiari.

There are also other museums in Anghiari, such as the State Museum and Misericordia Museum.

You can find the State Museum in Palazzo Taglieschi where it housed its prestigious art collection, including the polychrome wooden Madonna made by Jacopo della Quercia.

✔ Visit various castles and palaces.

Like the other medieval towns in Tuscany, Anghiari comes with its fair share of historical castles and palaces. Some of these are the Castle of Galbino , which was made back in the year 1000, and the Castle of Sorci , which now houses a highly acclaimed traditional restaurant.

Where to Stay in Anghiari

There are many great places to stay in Anghiari. A couple of these are Hotel La Meridiana and Locanda Del Viandante B&B .

For more options that fit your budget range and preferences in amenities, I suggest heading to Booking.com .

Bonus: Unique Day Trips from Tuscany

Just to throw in a couple of bonuses for you. Here are some great day trips in Tuscany and from Tuscany.

⭐ Florence American Cemetery

Car travel time: 40 minutes (not near a train nor town but easy access off the highway outside Florence)

For you Americans or history hounds, we chose to stop on our way back from Sienna at the Florence American Cemetery (free parking and admission). This pristine park pays tribute to the 4,402 American soldiers buried there who lost their lives during WWII, pushing up the length of the Italian countryside to clear the enemy lines. 

What a perfectly preserved place of peace. Extremely somber and mesmerizing and important and impactful. Be sure to walk to the top of the hill to read through the history of the route the battalions advanced now and forever etched into stone.

A very special place.

⭐ Asmana Wellness World Firenze

Italy is known for its wellness centers. It’s part of their culture of health.

Asmana Wellness is a wellness center and spa just outside of Florence. I’ve had multiple friends who have raved about it.  From the fresh juices to the saunas, wellness water journey, and even napping spaces, it’s the perfect place to rejuvenate your body and mind!

To get to Asmana, it’s best to have a car. However, you could take a combination of a train + bus + a little walking. 

⭐ Bagni Di San Filippo

About a 2 hour drive from Florence, Bagni Di San Filippo is an amazing giant natural mineral hot spring. It is a fabulous free way to spend a day. The white calcium waterfall seemingly frozen in time holds hot waters careening down it with cut out tubs perfect for lounging in. Named the white whale, this beast of a beauty was super relaxing and didn’t cost us a cent!

⭐ Portovenere

Located about 2.5 hours from Florence is the seaside picturesque town of Portovenere. We originally planned to take the dayboat from La Spieza to Portovenere through to Cinque Terre. However, upon arrival at the ticket booth, we discovered the seas were too strong for the ferry to turn the corner past Portovenere to Cinque Terre.

So we changed plans and chose to explore the seaside harbor town of Portovenere instead. The harbor holds multi-colored building facades and winding streets lined with shop after shop of food and flavors to fill up your day. Portovenere ended up being one of our favorite stops and less crowded than Cinque Terre!

⭐ Civita di Bagnoregio

Civita di Bagnoregio is one of the coolest towns in Italy. You can only access this quaint medieval town via the pedestrian bridge. The hill which holds Civita di Bagnergio is eroding so there aren’t many inhabitants left. Yet is still has some charming shops and restaurants and is one of my favorite day trips from Tuscany.

⭐ Lucignano

An unlucky day of the week choice for us as the museum holding the Tree of Love was closed on the Tuesday that we visited. The story of the golden gilded tree that took over a hundred years to craft led us to Lucignano but the charming concentric circling cobblestone streets on our cloudy day there brought us back in time.

We only had time for a quick stop in the quaint Collodi, but we got a glimpse of the Pinocchio crazed town including the tallest Pinocchio in the world.

How many days do you need in Tuscany, Italy?

The amount of time you need in Tuscany depends on how much you want to see. You most likely can’t see it all. I’ve spent over 4 months traveling throughout Tuscany and haven’t seen everything!

Some people come via cruise for a day and pop into Florence and maybe Lucca. Others stay for a week driving around to multiple small villages and larger towns.  And some, like myself, stay for months.

My advice is to get clear about what is important to you. When you are on your way home from your trip, what do you want to feel? What will you be glad you experienced?  If you also want to feel refreshed, remember that you don’t need to see it all. 

No matter how much time you have in Tuscany, I think Tuscany is best experienced by doing these three things:

✔️ Visiting a popular town (such as Lucca or Florence)

✔️ Visiting a smaller village

✔️ Seeing the rolling green hills (which can be done in conjunction with visiting a winery)!

What is the best time to visit Tuscany?

The best time to visit Tuscany is the Spring or Fall. The shoulder seasons essentially are when the crowds dissipate, the weather is a bit cooler and you can really enjoy the beauty in Tuscany.  Of course, truly you should visit Tuscany during the time of year that best suits your preferences. 

How to get around Tuscany?

To get around Tuscany, you can take the train, rent a car or take a bus. The other more expensive option would be to hire a driver.

If you are staying outside of the city center, I would recommend renting a car. It’s truly the best way to see the Tuscan rolling countryside and smaller villages.

FAQs about the Best Towns to Visit in Tuscany

Curious about the best towns to visit in Tuscany? Here are some of the most common questions:

Which is the prettiest part of Tuscany?

Cortona and San Gimignano are among the prettiest towns in Tuscany.

Going to Piazza Garibaldi in Cortona will give you a fantastic vantage view of its surrounding hills and valley. And if you prefer a charming cityscape, San Gimignano offers the iconic medieval towers Torre Grossa and Torre Rognosa. You can even climb inside these towers to better appreciate the panoramic view of the Tuscan countryside.

Check out some Tuscany inspiration:

Where are the best areas to stay in Tuscany?

Florence is one of the best areas to stay in Tuscany. It’s the capital city and the region’s primary tourist hotspot, which gives you a wide range of options for accommodations that fit any budget range. Also, a lot of attractions and must-try activities are conveniently nearby.

Siena is another good base in Tuscany. It’s located in the center of the region and will put you close to other must-visit places in Tuscany.

What is the safest city in Tuscany?

Florence is the safest city in Tuscany with a safety index of 70. It’s even one of the safest cities in Italy. 

You don’t have to worry about going to other places in Tuscany as well. Tuscany is considered one of the safest regions in Italy so exploring its glorious towns won’t pose too much of a risk.

However, keep in mind that safety precautions are still advisable, especially in touristy areas where pickpockets and the like may be present.

What is the most famous part of Tuscany?

The historic cities of Florence and Siena are among the most famous parts of Tuscany.

Florence is Tuscany’s main tourist hotspot and is known as the birthplace of the Renaissance. On the other hand, Siena is home to the world-renowned cathedral of Piazza del Campo, where the famous Palio horserace is held twice a year.

Pisa is also high on the popularity list. It’s mainly known for its leaning tower but also for the Square of Miracles and Arno River, to name a few.

What town is the heart of Tuscany?

Florence is mainly considered as the heart of Tuscany but others also take Pienza as the real heart of Tuscany.

Pienza is a Renaissance town that offers the most picturesque areas in Tuscany. It’s nestled on Tuscan hills where you get to see Renaissance palaces and the unobstructed view of the Val d’Orcia landscape.

If you’re going on a drive through the heart of Tuscany, your route will pass through Pienza, Montepulciano, Monticchiello, Val d’Orcia, and Bagno Vignoni.

What are some non-touristy towns in Tuscany?

Pitigliano, Barga, Suvereto, and Arezzo are some of my recommended non-touristy towns in Tuscany. You can enjoy a lot of fun activities, explore historical places, and bask in the magnificent natural view in these places without being thrust into overly crowded places.

What are the best towns near Florence, Italy?

San Gimignano, Monteriggioni, and Volterra are among the best towns near Florence, Italy. You can easily explore them by car or public transport if you choose to stay in Florence. 

Final Thoughts about the Best Towns in Tuscany

There are so many amazing towns in Tuscany. Venture out, explore the countryside, the villages, the olive farms, the wineries. Stop and enjoy the views.

My recommendation when checking out these best towns in Tuscany: Don’t try to see it all. Plan your meals around siesta so you aren’t left hungry. Go a little off the beaten path where there aren’t so many tourists. Have conversations with locals.

Enjoy all that Tuscany has to offer!

About the Author

Michelle Schomp is the co-founder and main writer of Passport Explorers.

She loves to explore new places together with her husband and three kids. And as they travel the world and gain new experiences, she loves to share everything she’s learned with all of you!

You can find more of her and her family’s adventures on YouTube .

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PRIVATE Full-Day Siena, San Gimignano and Chianti from Florence.

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Get out of Florence for the day to see other Tuscany highlights on a private tour to Siena, San Gimignano and Monteriggioni. Reaching these countryside gems can be difficult without a car, but door-to-door transport and all logistics are arranged, so you can focus on taking in sights like Siena’s famous Piazza del Campo and the UNESCO-listed medieval towers in San Gimignano.

Complete the experience with an optional private lunch at a hand-picked Chianti farm or winery.

PRIVATE Full-Day Wine Experience in Chianti Classico.

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Treat your senses to a memorable day in the world-famous Chianti wine region on this private tour from Florence. Travel in a luxury minivan through Chianti’s unmistakable landscape of historic vineyards, rolling green hills and medieval villages, with a private driver at your disposal throughout the day. Taste renowned Chianti wines and authentic Tuscan cuisine at estates of your choosing, or let your local driver make suggestions for the best places to wine, dine and explore. 

PRIVATE Full-Day Tour of Pisa, San Gimignano and Siena from Florence.

The UNESCO-listed towns of Pisa, San Gimignano, and Siena are among Tuscany’s most beautiful attractions, but visiting all three in one day is a challenge. Skip the train and save hours with this private minivan tour from Florence, leaving you enough time to explore each of these historic gems at your own pace. Take in the iconic Leaning Tower of Pisa, San Gimignano’s medieval old town, and the majestic cathedral in Siena. 

PRIVATE Half-Day Tour: Chianti Classico Wine Experience

Dedicate one day to a breathtaking visit of ancient vineyards and medieval villages in the famous landscapes of the Chianti wine region. Travel in a luxury minivan through rolling green hills and medieval villages, with a private driver at your disposal throughout the day. Tour some of the best small, organic family-owned wineries in the area where you can learn about traditional production methods and taste local artisanal products such as extra virgin olive oil and renowned varieties of wine such as Chianti Classico. The private tour can be customized according to your preference: include an optional authentic Tuscan lunch on a local farm!

PRIVATE Full-Day Siena and Chianti wine Experience from Florence.

Leave behind the bustling city of Florence with a private full-day tour in a luxury Mercedes Minivan. Stroll through the Gothic streets of Siena and discover the black-and-white art and architecture of its historic center, a UNESCO heritage site. Taste renowned Chianti wines and authentic Tuscan cuisine in famous family-owned cellars of local olive oil and aged balsamic vinegar.

PRIVATE Full-Day Brunello Wine experience from Florence.

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Wine lovers, dedicate a day to the legendary Brunello! Embark on an extraordinary 9-hour guided tour from Florence. Travel in a luxury minivan through rolling green hills and historic vineyards, with a private driver at your disposal throughout the day. You will visit Montalcino, a small medieval town south of Siena, which is the cradle of the fantastic Brunello! Experience the beautiful and suggestive medieval stronghold and location of the finest wines in the world. Taste wines from small producers or from the best-known brands. You will witness the production process and have lunch at their table while savoring their wines!

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Lunch in organic Farm PRIVATE Tour: Food & Wine Experience in Tuscany

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11 Enchanting Towns in Tuscany for Your Bucket List

• Isabelle Hoyne
• January 24, 2024

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I’ve been there before – overwhelmed by the sheer volume of beautiful Tuscan towns there are and trying to figure out what the best towns to visit in Tuscany really are….and how are you ever going to fit them into your itinerary? There are many beautiful towns in Tuscany, ranging from hill top hamlets to coastal delights. This guide walks you through the best towns in Tuscany Italy , helping you to make your itinerary planning that little bit easier.

As regions go, Tuscany is quite a perfect one. Famous as the home of Florence , birthplace of the Renaissance and its iconic Duomo, the impact that the glory days of Florence had on the wider region of Tuscany can be felt everywhere you go. 

The Tuscan landscape inspired many a great masterpiece by Florentine artists and in turn, the city of Florence and to a lesser extent, Siena , provided alliances and wealth to many of the towns that are dotted around the region. 

Many of these former strong-holdings are now well-known as the hill towns of Tuscany, having been placed more often than not on elevated, rocky outcrops that guard the countryside below. Many, to this day, retain a distinct medieval aesthetic and thus carry with them a very unique character and charm.  

The history of some towns in Tuscany stretch back even further than that – to the Romans and the Etruscans – and some, even, to the Bronze Age. For lovers of history, the region of Tuscany and its small towns is a fascinating one. 

History aside, what else is there to this abundant region that makes it so perfect? Well, there’s the fact that mountain lovers can both ski and in winter and hike in summer in Tuscany’s mountain ranges. 

And let us not forget either the god-given tapestry that are the softly undulating hills and cyprus trees of the Val d’Orcia that Tuscany has become so synonymous with.

RELATED READING | Tuscany Guide – How To Have A Very Memorable Tuscan Road Trip

Should you wish to dip your toes in the ocean, then you can have that too – via the Tyrrhenian sea along the Maremma coast. And, quite possibly the cherry on top, is the rich, bountiful food and wine culture of the region. 

Tuscan dishes are hearty and filling and local dishes vary from area to area. Tuscany also produces world-renowned wine, amongst its most famous being Chianti and the high-end Brunello di Montalcino.

If you’re a lover of wine, then it makes total sense to come to the source! Consider enhancing your experience with winery tours from Siena .

It can thus be said that discovering these small towns in Tuscany presents an intoxicating proposition. But what are the best towns in Tuscany to visit? The term ‘best’ is a very subjective one, meaning different things to different people.

So I’ve asked some fellow travel bloggers, each lovers of the Tuscan region too, to contribute some of their must see towns in Tuscany to give you a more holistic view.  

These best towns in Tuscany to see I have split out as follows: 

• The most beautiful small town in Tuscany to visit
• The best wine towns in Tuscany
• The best medieval towns in Tuscany, Italy
• The best hilltop towns in Tuscany
• Best coastal town in Tuscany

You’ll find that even the above categorisation is a bit imperfect, as it’s very difficult to corral towns into one distinct category – for example, the town of Montepulcianio is all of the above, except for a coastal town (hint: make sure to include it on your itinerary).

But I’ve provided enough information below for you to decide if a town is for you or not! Happy planning!

Essential links for your Tuscany Trip Planning

Book your flights to Tuscany using Kiwi Book your Tuscany car rental via Rentalcars Top-rated Tuscan tours and experiences ☆ Greve in Chianti Wine Tasting and Winery Tour (for Chianti Classico lovers) ☆ Private Truffle Hunting Experience with Wine and Lunch ☆ Lunch and Cooking with a view in a Brunello Winery (Tuscan cuisine & Brunello – a win win!) ☆ Siena Vespa Tour Including Lunch at a Chianti Winery ☆ Tuscany Hot Air Balloon Flight (if you’re looking for something really special) Top places to stay in Tuscany: AdAstra Suites (quirky Florence boutique hotel) // Borgo Pignano (ultimate luxury) // Villa Poggiano (refined villa hotel) // Plum Guide (dreamy vacation rentals with pools – read my roundup of Tuscany’s best villas with private pools ) Don’t forget to pack : Tuscany, Italy: Small-town Itineraries for the Foodie Traveler // Universal travel adapter  //  these **fantastic** compression packing cubes // Under the Tuscan Sun , by Frances Mayes

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Before you decide on what Tuscan towns you’re going to visit, you should first figure our how you’re going to get around and then choose your towns accordingly.

While you can get around to the larger towns in Tuscany relatively easily via the train network, if you are to reply on public transport to get around Tuscany, you will find it difficult to reach the most small towns in Tuscany as you will be reliant on regional buses that often have sparse and infrequent timetables.

For that reason, I would highly recommend that you rent a car in Tuscany.

I always use  rentalcars.com  when hiring a car abroad and our road trip to Tuscany was no different. I like them for the following reasons:

• You can compare all car rental companies in a given destination. They also have superior filtering options too, so you really can drill down to what you’re looking for – even to the deposit amount and payment type. 
• All the info you need for your relevant booking can subsequently be found in their convenient app – no print outs necessary.
• You can often amend/cancel your booking with no additional charges.

If you don’t fancy driving, then I would instead recommend that you base yourself in some of the larger towns in Tuscany and see more of the best little towns in Tuscany via guided tours and day trips. You can learn more in the section directly below.

This is a tough question to answer, and the answer to what the best towns to stay in Tuscany Italy are is dependent firstly on how much time you have to spend in Tuscany, and secondly, which must-see towns in Tuscany pique your interest the most, and where they are located.

If you are visiting Tuscany for a shorter period of time, then staying in Florence and doing day trips from there might make more sense. You can see and book day trips from Florence here .

However if you do have 5 or more days in Tuscany then great! Make sure that you allocate plenty of time within your Tuscany itinerary to discover a smattering of the more famous towns in Tuscany, together with some of the more under the radar, beautiful small towns in Tuscany.

I’d highly recommend booking accommodation at a Tuscan villa when in the countryside, whether that be one operating as a hotel or as a vacation rental. It’s truly the best way to get that rustic, Tuscan experience.

If you are concerned about being close to a town, exploring the best small towns in Tuscany to stay can be a great idea.

What are the best Tuscany towns to stay in?

• Chianti : some of the best Tuscany towns to stay in to access the Chianti region include Greve-in-Chianti , San Gimignano and Volterra .
• North Tuscany : one of the best small towns to stay in Tuscany’s north is the famous walled town of Lucca .
• Val d’Orcia : I’d highly recommend positioning yourself close to Montepulciano if you’re visiting the glorious Val d’Orcia – it’s one of my favourites and also one of the best Tuscan towns to stay in due to how fabulous the town is itself, together with how well positioned it is for exploring the area.

Booking a luxury villa in Tuscany

If you’ve decided (or need some convincing) that booking a luxury villa in Tuscany is the way to go, then I’ve pulled together a curated list of the best villas in Tuscany , all with pools, that are split out by region to help you find one in a location that’s perfect for your needs.

RELATED READING | 19 Beautiful Villas In Tuscany With Private Pools [2024]

Booking a hotel in Tuscany

If you’d prefer to be waited on hand and foot, you can discover some great villas operating as hotels in Tuscany to stay in by using the below interactive map. I’ve also included VRBOs in Tuscany too in case you want to search for a villa that way. Just enter your dates and away you go!

The best towns in Tuscany to visit

Montepulciano .

By Isabelle, from Cultured Voyages

Situated high on a rocky outcrop, hewn into the bedrock sits the ancient town of Montepulciano, which presides regally above the expansive plains and hills of the Val d’Orcia below.

This medieval hill town is a very special one, carrying a distinct air of uniqueness, spectacular views from its town walls and an ancient and interesting history.

Montepulciano is perfect both as a base from which to explore the other Tuscan villages and historic towns of this beautiful region, or indeed to just pop into for a day trip to take a wander around its ancient streets, admire its beautiful buildings and bask in the panoramic views of the rolling hills.

Follow the cobbled streets upward to the historic town center and the marvelously medieval Piazza Grande, where you can still see the Medici insignia emblazoned in the square.

This imposing walled town is also home to a number of excellent restaurants – two that I can highly recommend.

First, is Osteria del Borgo , a traditional restaurant located just inside one of the main gates of the old city walls and offers hearty Tuscan dishes and stunning views of the beautiful countryside from its outdoor terrace.

Second, is La Bottega del Nobile , a special winebar-restaurant with tables deep down in the wine cellar, glorious food and an extensive wine list.

Situated in the heart of a wine region, Montepulciano is famed for its very special wine, Vino Nobile di Montepulciano. There are lots of great local wineries nearby, so this is the perfect place to undertake some wine tasting if you wish to include it on your Tuscan itinerary.

RELATED READING | 11 Best Wine Tours in Montepulciano: 2024 Curated Picks

By Chris from Amateur Traveler

Montalcino is one of those beautiful hill towns that Tuscany is known for. The history in the area goes back to the Etruscans, but the town today is protected by its five sided Fortezza which dates back to the 1300s.

These days the town is known for the Brunello wine produced from the vineyards that cover the slopes of the hill. Brunello is one of the most popular of the Italian red wines and there is no better place to sample Brunello than in the Tuscan town which it hails from.

You can walk all the streets of the town in 15 minutes and still have time left over to find a glass of wine. There are a number of small enotecas in town where you can stop for a glass or a bottle of wine, including one in the Fortezza.

Take your time as you walk through town and peek into the small private courtyards of this charming town. 

Start at the Fortezza where you can climb up to the walls to get the best view in the town. The Main Street runs from the Fortezza across the hill to the humble Sant’Agostino gothic-style church.

Across the street from the church is the small Riuniti Museum which has a collection of art from the 14th to the 20th century. The museum is run by the city and the Catholic diocese and its best pieces are religious art.

After the hustle of Florence or Siena, Montalcino is a quiet interlude. The best way to experience Montalcino is to rent one of the villas near town and make it a base for operations in Tuscany. You can easily do day trips from Montalcino.

Without shadow of a doubt, one of the most beautiful towns in Tuscany is the renaissance town of Pienza.

Pienza is located close to Montepulciano, meaning that it is extremely easy to combine a visit to both of these towns in one day, or to visit one while based in the other. On the route between Montepulciano and Siena also, it’s extremely easy to stop off in Pienza if you are transiting between the two.

Pienza is often regarded as the most beautiful town in Tuscany, with its well-preserved Renaissance architecture and charming atmosphere that transports visitors back in time.

Upon entering the old historical center of Pienza, it feels like you have stepped into a time warp, as much of the town’s major features date from the Renaissance. In the 15th century, Pienza (then known as Corsignano), struck gold when a citizen from this formerly humble village was elected Pope Pius II. 

He set about making Pienza the ideal Renaissance town, enlisting the help of famous architect Leon Battista Alberti to remodel the town based on humanist urban planning principles.

Upon Pius’ death, the redevelopment halted and what remains today has been virtually untouched since that time. Its beautiful architecture from this period makes it one of the most prettiest towns in Tuscany.

A UNESCO World Heritage town, Pienza is also home to Pecorino Di Pienza, a sheep’s milk cheese that is added to many of Tuscany’s most delicious dishes and cheese shops are smattered amongst the historic buildings of Pienza’s winding streets.

With its incredibly well-preserved Renaissance buildings and its position as the capital of pecorino cheese, Pienza is an extremely compelling day trip proposition on a Tuscan road trip.

It offers astounding views of the surrounding fields and cypress trees of the Val d’Orcia, making it by far and away one of the top small towns in Tuscany Italy to visit.

San Gimignano

By Or from My Path in the World 

Also known as the Town of Fine Towers or Medieval Manhattan, San Gimignano is a walled hilltop town you don’t want to miss in Tuscany . Just by driving towards it, its unique skyline makes it easy to understand why it is one of the most picturesque towns in the region.

Thanks to its iconic well-preserved tower houses and stunning medieval architecture, its historic center was declared a UNESCO World Heritage Site, and indeed, strolling through San Gimignano feels like stepping back time.

Some of the main points of interest of this enchanting town include the Palazzo Comunale (the highest of the towers and an art museum), Porta San Giovanni, and Duomo di San Gimignano (Collegiate Church of the Assumption of Mary), but you’ll find plenty of beauty in each and every corner.

Plus, there’s no shortage of panoramic lookout points.

Although it’s a small place, this town is also known for its fantastic food, saffron production, and white wine (Vernaccia di San Gimignano), so you’ll also find many amazing restaurants, wine bars, and wine shops here.

A few to check out are Le Vecchie Mura, Il Ceppo Toscano, and La Vecchia Nicchia. San Gimignano is among the charming Tuscany small towns, offering a delightful culinary experience alongside its historical attractions.

Last but not least – located in the central Piazza della Cisterna, don’t miss Gelateria Dondoli, which was the Gelato World Champion more than once.

It is especially known for a few unique flavors you have to try, like Crema di Santa Fina (cream with saffron and pine nuts), Dolceamaro (cream with aromatic herbs), and Champelmo (pink grapefruit and sparkling wine).

By Karen from Bewitched By Italy

Lucca is one of the most popular medieval towns in Tuscany, with Etruscan and Roman origins. In the Middle Ages it was an important city-state, and the architecture and historic centre that are the main attraction for tourists date from this period.

The number one must-do activity here is to walk along the top of the Lucca city walls . These form a complete circuit of around 4 km, built in the 16 th century but incorporating earlier sections.

The walls are not just of historic interest: they are wide and form an extensive area of parkland, with trees, cafés and children’s play areas. Lucca is considered the best city in Tuscany to visit, offering a unique and enjoyable experience for tourists.

Elsewhere in the city, look out for the remarkable Piazza Anfiteatro, built on the site of the old Roman amphitheatre. Unlike most piazze this one is round, and shops and restaurants have been built into the spaces where the arches once were.

At the centre of Lucca is the Cattedrale di San Martino, notable for its 13 th century black wooden figure of Christ and a painting of the Last Supper by Tintoretto. 

You can also visit the Palazzo Pfanner (a palace and garden that is now an art museum) and the Puccini Museum, in the house where the composer was born. Or climb to the top of the Torre Guinigi, a 14 th century bell tower, for views across the city.

There are several places to eat around the Cathedral area. I enjoyed a meal at the Aria Café Restaurant in one of the nicest towns in Tuscany.

Monteriggioni

Martina – PlacesofJuma

A really amazing tip for a stop on a road trip is the wonderful medieval village of Monteriggioni in Tuscany . The historic fortress, which is located on the hill Monte Ala, is especially beautiful and due to its location, it offers a fantastic view over the Tuscan countryside.

In the center of the complex enchants a picturesque old town, which can be explored via a short easy walk. Among the most important attractions are the well-preserved defense towers and the city wall, which you can even climb up.

Monteriggioni is a gem among the Tuscany cities, showcasing the region’s rich history and captivating landscapes.

The medieval flair of Monteriggioni is unique in Tuscany, and that is why a large medieval festival is held here once a year in the summer. Absolutely worth seeing is also the Piazza Romana directly in the center.

This picturesque square is the main square of Monteriggioni and with a coffee or a glass of wine in one of the good local restaurants there you can watch the hustle and bustle.

If you love wine, don`t miss to try the regional red wine “Chianti Colli Senesi Monteriggioni”, whose vines grow in the vineyards around the castle.

Another interesting place to visit is the church of Santa Maria Assunta, which dates back to the 13th century and is one of the oldest buildings in the old town.

If you want to learn more about history, it is best to check out the museum “Monteriggioni in Arms”, where you can learn more about the rich past of Monteriggioni.

These attractions add to the allure of Tuscan cities, providing a glimpse into their fascinating heritage and cultural significance.

All in all, Monteriggioni is a real highlight in Italy and among the best towns to visit in Tuscany should not be missed on any perfect Tuscany Road Trip!

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By Chrysoula, from Travel Passionate

One of the top towns to visit in Tuscany, the Tuscan hilltop town of Volterra lies conveniently close to Florence. The town has a rich history dating from Etruscan times (5th century BC) when it was one of 12 powerful centers.

Remnants of its ancient defensive walls, gateways, and its strange layout are all credited to the Etruscans!

Enjoy a break from driving and slip on comfortable shoes as there is much to see in this pretty town. The center of the town has medieval streets and squares. The Palazzo dei Priori is the oldest town hall in Tuscany.

The 12th century Duomo – Cathedral of Santa Maria Assunta- is beautiful. Much of it was renovated in the Renaissance style and it has a richly decorated ceiling and numerous paintings including a famous fresco by Benozzo Gozzoli (1479). 

If you enjoy history there is the Guamacci Etruscan Museum and numerous Roman monuments to see including Roman baths, a forum, and an amphitheater. The magnificent Medici Fortress sadly cannot be explored inside as it is used as a top security prison.

Volterra is world-famous for its alabaster carving, so is perfect for souvenir shopping. During mid-March, late October, and early November there are celebrations showcasing local products that include white truffles, cheeses, olive oil, and chocolate.

Volterra stands out as one of the Tuscany best towns, offering not only unique craftsmanship but also delightful culinary experiences during these festive seasons.

By Kathryn from Wandering Byrd

Cortona is built on the top of a hill, with breathtaking views across the surrounding countryside. The town is quintessentially Italian- think beautiful plazas, cute streets and lots of history.

In fact, the villa used in the movie ‘Under the Tuscan Sun’ is located just outside Cortona (you can even rent it for a week’s holiday!)

Cortona is over 2000 years old and its history is full of Greek and Roman stories. One of the biggest attractions in the town is the Accademia Etrusca- a museum full of artefacts and things found in the area.

It’s spread over 5 floors in a 13th century building and is well worth a visit. There are several other museums and historic places in the town to visit, including the Cathedral and the main square.

If you’re more interested in Italian food and drink than history, head to La Bucaccia- set in a medieval stables and famous for its beef and pasta dishes. For wine, you can’t beat Taverna Pane e Vino, where you can enjoy Tuscan and Italian wines along with bruschetta and cheese.

If you’re campervanning in Italy , there are some wonderful campsites to stay at within walking distance of the town, but if you’re road tripping by car, there are plenty of hotels and BnBs to choose from.

Exploring the top Tuscany towns becomes even more convenient with a range of accommodations available to suit different preferences and travel styles.

Cortona is also famous for its jazz festival, which usually happens over several days around the end of April and is definitely worth arranging your travel to be there for the festival atmosphere which spreads through the town.

By Isabelle from Issy’s Escapades

Pitigliano is one of Tuscany’s famous ‘Tufa’ towns, which are towns that have been carved from volcanic (or ‘tufaceous’) rock.

Pitigliano is the most recognisable Tufa town in Tuscany, in part due to the dramatic setting it occupies atop a particularly elevated and prominent rocky outcrop. It is undeniably one of the Tuscany must-see town for its remarkable geological features and rich historical heritage.

South of Montepulciano and close too to the thermal mineral waters of Bagno San Filippo, its relative proximity to other popular Tuscan towns, together with its fascinating historical and cultural heritage, make Pitigliano one of the best small towns in Tuscany to visit. 

Pitigliano’s earliest signs of inhabitance are rather ancient, dating back to Neolithic times.

There are also signs to suggest that there was an Etruscan community here in the 6th century, followed by the Romans, before the Medicis left their mark on this historic town in the 16th century, with the construction of an aqueduct that can still be seen to this day in the town center.  

Extremely interesting too, is the fact that Pitigliano is also known as “Little Jerusalem”, due to the role it played as an important refuge to the Jewish community who fled persecution from other areas of Italy from the 14th century onwards.

They played an important role of shaping the culture of this interesting Tuscan town and it is possible today to visit the former Ghetto area of the town. 

As one of the best hill towns in Tuscany worth visiting, there is a lot to fit in during a visit to Pitigliano. Make your way to the north-western part of the town to discover ancient Etruscan walls and the Porta Sovana , an entrance to the town hewn from the tuff that leads to the vie cave and the necropolis of Sovana .

The vie cave (meaning, simply “excavated roads”) are a bewildering set of tunnels – as no one knows for certain why they exist – which you can explore with or without a tour guide. Look out too for the “ Tempietto “, which is a small temple that may lead back to Etruscan times.  

As such a historic town in Tuscany, it is a given that Pitigliano is home to some museums, should you wish to learn more about its heritage.

These include the Alberto Manzi Outdoor Archaeological Museum, which brings Pitigliano’s history to life, the Civic Archaeological Museum of Pitigliano, which includes a range of artefacts from the Bronze Age to the Etruscans , and the Palazzo Orsini and Museum of Sacred Art. 

The lovely town of Barga is one of the most important hilltop towns in Tuscany, known also as the Gem of the Garfagnana .

The Garfagnana is an area within the province of Lucca, in Tuscany’s north-west, that is famous for its sprawling and varied landscape. Barga is one of the top towns in Tuscany to visit or base yourself if you love the great outdoors and all the activities that go with it!

The town itself is contained within a marvelous mountain setting and is around an hour from the best Tuscan town to visit, Lucca. It is a wonderful location in which to wander narrow streets and discover the pastel-hued Renaissance buildings housed within Barga’s centre.

Historically, the town of Barga was linked to the powerful Renaissance city of Florence for centuries and reaped the rewards that this strategic alliance offered.

In this regards, it is therefore thoroughly unsurprising that you will the Medici coat of arms of the columns of the Florentine Marzocco (the lion symbol of Florence’s political strength) beside the Loggia dei Mercanti . This was the town’s medieval marketplace located in the town’s main square, Piazza Salvi.

Barga is also home to one of the most important Romanesque churches in Tuscany, the Cathedral of San Cristofano. The church sits high above the town, on a vantage point called the “Arringo”, where citizens used to meet to discuss important matters and also, for executions.

Rather interestingly, the Arringo has earned itself the nickname of “ Prataccio “, or “nasty lawn” as a result of the latter!

Portoferraio

By Emma from Emma’s Roadmap

One of the cutest towns in Tuscany is definitely the small harbour city Portoferraio on the island of Elba. If you’d like to get away from mainland Italy and explore more of its coast, this is definitely the place to be!

The name Portoferraio actually means iron harbour in English and refers to the history of this city in Tuscany as the place to trade iron. However, this is not the main reason why Portoferraio is mostly known.

In 1814, the one and only Napoleon Bonaparte was banned to the island of Elba and lived in Portoferraio for almost a year. Because of this, Portoferraio also attracts many tourists.

One of the top attractions in this harbour town is one of Napoleon’s houses, Villa dei Mulini. Here, you can experience how the emperor used to live in exile and learn more about his history!

Another great activity in this city is Martello Tower. This tower used to be a prison and is located right at the harbour with an amazing view of the bay of Portoferraio. Originally, it was built as part of a defense infrastructure for the island, but right now you can visit it together with its museum. It is definitely worth exploring while visiting one of the best Tuscan towns.

Of course, you can’t visit the island Elba or Portoferraio without trying the local cuisine! Very popular dishes you should try on the island are Rio-style rockfish, stuffed sardines and boiled octopus. Also, don’t forget to try one of the local wines while visiting Portoferraio, one of the best coastal towns in Tuscany!

To aid you in your trip planning, I’ve included the above best Tuscany towns to visit on a map.

Unless you have at least 10 days, it is highly unlikely that you will be able to visit all of these towns in Tuscany Italy in one visit, so choose a handful that pique your interest and combine them other visits to the best cities in Tuscany like Florence and Siena. 

How to use the map : Use the toggle on the left on the header bar to open/close map contents. You can also zoom in and out and interact with the saved items on this map. To save the map to your own Google account, click on the star sign beside the map title on the header.

How to get to Tuscany

Tuscany is home to two airports; one in Florence and another larger airport in Pisa. You may find more extensive flight schedules to Pisa so as a result, prepare to be flexible on which you fly in and/or out of. 

Both airports are well connected to other cities and larger towns in Tuscany via the train network. It’s also completely possible and not too taxing to fly to Rome and either drive or get a train to Tuscany. 

Having used the train network in Italy throughout various regions of the country, I can confirm that it’s an extremely reliable and efficient way to travel. Major cities are well connected, with smaller towns in turn being well connected to a larger hub. 

Trains from Rome to Florence, for example are frequent (running at over 50 a day) and take only around 1 and a half hours. 

| TICKETS: Buy train tickets from ItaliaRail , or plan a route and purchase tickets via Omio . 

If you’d prefer to take a bus (I’d recommend a train, however, if budget is not a concern) then there are also numerous companies that operate bus routes within Italy. 

| TICKETS: Plan your route and purchase tickets here .

To fully experience the charming Tuscany villages, there are various options available to suit different preferences.

One of the best ways is to hire a car , as it offers the flexibility to explore at your own pace and venture off the beaten path. Driving through the picturesque countryside allows you to immerse yourself in the breathtaking landscapes and stop at multiple villages along the way.

If you prefer not to drive, public transport is another viable option. Trains and buses connect many of the villages, making it convenient to hop from one to another. However, do note that the frequency of public transport can be limited in some rural areas.

Alternatively, hiring a private driver provides a more personalised experience, with the convenience of door-to-door service and local insights. This option is ideal for those who prefer a guided experience or have limited time.

Lastly, joining a group tour can be a great way to discover the Tuscany villages with a knowledgeable guide. Group tours often cover popular destinations and offer the opportunity to meet fellow travellers.

Consider your preferences and priorities when choosing the best way to explore the Tuscany villages, ensuring you make the most of your visit.

When it comes to visiting the picturesque Tuscany villages, timing is everything. Each season offers a unique charm, so it ultimately depends on your preferences.

Springtime, from April to June, is a delightful period to explore the villages. The weather is mild, the countryside is blooming with colourful flowers, and the vineyards are alive with activity. It’s the perfect time for leisurely walks and outdoor activities.

Summer, from July to August, is undeniably the busiest season, with warmer temperatures and a lively atmosphere. If you don’t mind the crowds, you can enjoy vibrant festivals, open-air markets, and alfresco dining.

Autumn, from September to October, is a magical time when the landscapes transform into a breathtaking tapestry of golden hues. It’s the harvest season, and you can witness the vineyards and olive groves in full swing.

The weather is pleasant, and the villages are less crowded, making it ideal for immersing yourself in the local culture.

Winter, from November to February, brings a tranquil ambience to the villages. While some attractions and restaurants may have reduced hours, you can still experience the authentic Tuscan life and indulge in cosy evenings by the fireplace.

Overall, Tuscany is a year-round destination, and the best time to visit depends on your preferences, whether it’s vibrant festivals, blooming nature, or peaceful solitude.

Tuscan towns to visit – FAQ

Tuscany is a region in central Italy that covers an area of approximately 23,000 square kilometres (8,900 square miles). It consists of several provinces, including Florence, Siena, Pisa, Lucca, and more.

From the list of Tuscan towns included in this list, the best towns near Florence to visit are Volterra, San Gimignano, Monteriggioni and Lucca. 

Tuscany is quite heavily visited, so in order to find some less-frequented places, you’ll need to head a little off the beaten track. Some non touristy towns in Tuscany to visit would include the likes of Barga, Pitigliani (it’s well known but often gets overlooked) Collodi, Montefioralle and Certaldo Alto.

The truth is, that while you see the same names thrown about a lot, there are almost endless amounts of small towns in Tuscany to visit. The best thing to do is to decide on one smaller area within Tuscany and then head off in your rental car to discover some of them serendipitously. 

A good home base in Tuscany will depend on a number of factors, such as how long you plan on staying in Tuscany for and what areas of Tuscany you’d like to see.

Personally, I think the Siena region of Tuscany makes a fantastic base, as it’s fairly central; you’ll be able to easily access cities like Florence, Siena and Arezzo as well as be placed somewhat in the middle of the region, which means you’ll have a whole host of beautiful Tuscan towns within reach.

I discuss where to base yourself further in the relevant section above .

In order to get any sort of feel for the region, I’d plan to spend at least three days in Tuscany (not including Florence).

It’s the perfect region to explore deeply, however, so you can easily spend a week or more in Tuscany – in fact I’d highly recommend doing so. Read my Tuscany itinerary post to discover how to pass your time. 

The absolute best months to visit Tuscany are May and September. In May, temperatures are warm but not unpleasantly hot. The countryside is also quite lush, so if you want to see the rolling green hills that Tuscany is known for it’s the ideal time to do so.

September will be a bit hotter than May, but again, nothing unbearable which makes it a great time to go for some early-Autumn sun. The countryside starts to turn golden and the grape harvest also takes place, which will be particularly appealing to wine lovers. 

While Tuscany is renowned for its scenic countryside, the Val d’Orcia region is often considered the epitome of Tuscan beauty. Located south of Siena, it features rolling hills, cypress-lined roads, vineyards, and picturesque villages like Montalcino and Pienza.

Tuscany is home to several major towns that showcase its rich history and culture. Some notable ones include Florence, Siena, Pisa, Lucca, Arezzo, and Cortona. Each town has its own unique charm and attractions worth exploring.

While Tuscany has many captivating towns, Florence is often considered the heart of the region. Known for its Renaissance art and architecture, Florence boasts iconic landmarks such as the Duomo, Uffizi Gallery, and Ponte Vecchio. It offers a perfect blend of history, culture, and culinary delights.

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Hi there! I'm Isabelle, aficionado of immersive travel experiences and unique, luxurious hotels. You'll most likely find me camera in hand, or nerding out on research in advance of my next trip. A major foodie, history and scenery lover, nothing makes me happier than soaking in the atmosphere and culture of the destination I'm visiting.

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The Ultimate One Week in Tuscany Itinerary You’ll Want to Steal

By: Author Sophie Nadeau

Posted on Last updated: 15th October 2023

Categories Italy , Itineraries

Last Updated on 15th October 2023 by Sophie Nadeau

Spending a week in Tuscany is the perfect way to discover ancient cities and unique settlements with their churches, museums, and historic sites, but also, a more intimate part of the country, characterised by an authentic, simpler lifestyle. Best explored over the course of at least seven days, here’s our advice for spending one week in Tuscany .

Romantic and inspiring, Tuscany is an incredible Italian destination. During the last ten years, the region started a completely new trend in tourism, focusing on the promotion of its food and wine production, in close contact with nature, and placing value on the territory and its ancient traditions.

If this is the kind of adventure that you’re looking for, then get on board and explore the best things to do in Tuscany in a week .

Essential Things to Know about Tuscany

Traveling to tuscany, when to visit tuscany, where to stay in tuscany, one week in tuscany: places to visit and things to do, santa maria del fiore, piazza della signoria, galleria degli uffizi, before starting your second day in florence…, arno river and ponte vecchio, oltrarno, palazzo pitti and boboli gardens, sunset at piazzale michelangelo, leaning tower of pisa and piazza dei miracoli.

• Pisa National Museum and Pisa’s Lungarnos

Ancient Walls

Lucca cathedral, the towers of lucca and puccini museum, piazza del campo and the duomo, contrade museum, francigena street and monte dei paschi, torre grossa and other medieval towers, piazza della cisterna, vernaccia di san gimignano, day 7 in tuscany: chianti region.

Tuscany is an important region in Italy located in the central-northern part of the country, with a big portion of its boundaries facing the Tuscan Archipelago and the Tyrrhenian Sea.

The capital of Tuscany is Florence, however, there are many more important cities scattered around the whole region. Some of them will be included in this 7-day in Tuscany itinerary. The most important cities in Tuscany are Florence, Pisa, San Gimignano, Lucca, and Siena.

The best way to get to the region is to travel to Florence by train. Since the city is in a very central position in the country, traveling times are relatively short no matter where from you start your trip towards Tuscany.

Since Florence is the capital of Tuscany and the most important city in the area, there is a remarkable train station, Santa Maria Novella, that connects the city to the rest of the country as well as to many important cities in the Tuscany region.

Florence’s International Airport receives flights from several European cities, however, there are no flights from non-European countries arriving in Florence. For that reason, if you’re getting to Tuscany from out of Europe, you can travel to Rome or Milan and take a domestic flight or a high-speed train.

Moving around, instead, is better done by car, which gives you enough freedom to move from one town to another, exploring at your own pace and stopping anywhere on the road. The local roads are well-maintained and the highways are wide and safe in this part of the country.  

The region has quite pleasant weather all year round. The best time of the year to visit is spring when the temperatures are comfortable enough and attractions are not overcrowded or overpriced. 

During April, May, and June you will encounter plenty of sunshine too. August instead, is too hot while fall is another good alternative, as it is still not very cold, however, rain can be common in certain areas.

There are different alternatives. You can change accommodation for every town you visit, you can base yourself in Florence and, from there, take daily trips to every major town, or you can experience life in the Tuscan countryside and spend a week in a local agriturismo (farmhouse).

If that is the idea you like best, down below you will find the agriturismo accommodation I suggest you check out these Tuscany farmhouses:

Castello di Bossi: Close to the Chianti wine region, the farmhouse offers stunning garden views, free bikes, a seasonal outdoor swimming pool, a bar, a garden, and a tennis court.

The farm stay features private parking free of charge. Some units feature a seating area as well. There are different breakfast options as well as barbecue facilities. Check prices and availability here .

Agriturismo Crocino in Chianti: In the Chianti area of Tuscany, about 60 km from Florence, this gorgeous place offers accommodation with a restaurant, a garden, and private parking free of charge. Check prices and availability here .

Relais La Torre: A magnificent property for an unforgettable stay in Tuscany, this farmhouse is nestled within a large estate, among vineyards, olive groves, and woods. The stay includes a rustic Tuscan breakfast. On the premises, there is also a chapel from 1756. Check prices and availability here .

To make the trip easy and flexible, for you to enjoy your days without being extremely exhausted every evening, you will only find three main activities to do on each day of the visit.  And it is my strong suggestion to focus only on three major things each day.

This does not mean that there isn’t a lot more to do in the area, on the contrary, it gives you the chance to spend hours doing more than just visiting landmarks, it allows enough free time to mingle with the locals… and live like a local, because, in the end, that’s what Tuscany is all about!

Day 1-2 in Tuscany: Florence

It is a good idea to devote two complete days to Florence as there is a lot to see and discover in the former Renaissance capital of Italy. If you only have a short time, then be sure to check out our suggestions for one day in Florence . Otherwise, for a long weekend, check out our suggestions for how to spend 3 days in Florence .

The city hosts some of the most remarkable architectonic gems in the country, as well as stunning art museums, and picturesque cobblestoned alleys, all in one of the prettiest historic towns in Tuscany.

Upon arrival in Florence, head directly to the heart of the historic district (it’s a 10-minute walk from the main train station) to explore Florence’s Cathedral, Santa Maria del Fiore. 

In the same area, you will also be able to observe the impressive Giotto Campanile, the church’s bell tower, as well as Saint John’s Baptistery with incredibly detailed doors designed by Botticelli, one of the most remarkable Italian Renaissance artists of all time.

Locally known as the Duomo di Firenze , this cathedral is one of the country’s best examples of the Italian Renaissance. The main characteristic of the building is the imposing cupola that was designed back in 1436 by Filippo Brunelleschi. 

This ceiling is deemed to be the biggest masonry dome built in history. From the centre of the church, when you look up at the dome, you can appreciate one of the most refined frescoes ever made in Europe during the historic period.

If time allows, it is a good idea to have a close-up look at the. You will be able to check out unique details of the intricate work of engineering and amazing city views. Check ticket details here.

Your second stop on this Firenze itinerary will be the main square, Piazza della Signoria, only steps from the cathedral. In the area, you can visit the inner courtyards of Palazzo Vecchio (for free) , or purchase a ticket for a complete tour of the Palace for further details and information about the history of the city.

At the main gate of the Palace, you will be stunned at the famous replica of the famous Michelangelo’s David. This is not the original sculpture, which is housed in a nearby art gallery (L’Accademia), which you can visit on your second day in Florence.

Right on the street that starts at Palazzo Vecchio to reach the Arno River, stands Florence’s Uffizi, one of the most incredible art exhibitions in the world that features stunning paintings and works of art, including a Renaissance art collection featuring works by Da Vinci, Caravaggio, and Botticelli, among others.

Since the place is incredibly vast, the best way to enjoy the highlights of the exhibitions is by booking a tour with a local guide. Check prices and availability here.

If you are a fan of art and are still willing to see the original Michelangelo’s David, then make a short early visit to Galleria dell ’ Accademia . The earlier you go, the less crowded it will be. In the museum, which is mostly devoted to the art of Michelangelo, you can also explore an odd Museum of Musical Instruments.

The Arno River is another landmark in the city, which divides it into two distinctive parts. Crossed by several bridges, the most famous of all is Ponte Vecchio.

Ponte Vecchio (which means old bridge, in Italian) is an ancient bridge that today hosts houses and shops. This medieval bridge is the road you will take to visit the Oltrarno district, on the other side of Florence to visit the next attractions.

Devote the whole afternoon to wander the streets of the bohemian neighbourhood of Oltrarno, with its bohemian cobblestone streets plenty of trees, cozy wine bars, and restaurants, and a less touristic vibe that is incredibly attractive.

This is the best area for an authentic Florence meal minus the high price tags you are certainly going to pay in the historic district, so do your wallet a favor, and eat in Oltrarno! 

Try: Alimentari del Chianti, a super famous eatery where to try a wide selection of Italian panini in Pitti Square.

The district has two major landmarks that you might one to explore, you can start by checking out the different areas inside Palazzo Pitti.

Built back in 1457 for a local family, the building was designed by Filippo Brunelleschi. Palazzo Pitti was also home to the powerful Medici family that ruled Florence for decades. 

This Renaissance palace houses an extraordinary collection of art that includes the works of Raphael, Caravaggio, and Tiziano among others and there are also organised tours like this one available.

The well-curated gardens of this palace are known as the Boboli Gardens, and it remains one of my favorite places to explore in Florence, offering unexpected city views as well. 

Inside this unique green space, you will find impressive fountains, symmetrical spaces, and bizarre baroque sculptures hidden in unexpected corners. If you are ready to add this visit to your Tuscany itinerary, then get your ticket in advance .

Assuring the best vistas in town, this is an unmissable meeting point where locals love to hang out, especially at sunset, after a hard day at the office. Piazzale Michelangelo is a gorgeous square and main observation point perfect to capture the best images of Florence.

But it is also a cool place to sit, enjoy a beer, and take in all the beauty that the capital of the Tuscany region has to offer.

End your day in town with a light meal and end your stay in Florence with Italian gelato . After all, Florence is where many people believe the Italian sweet was invented.

When in Oltrarno, it is a good idea to taste the gelato made by Gelateria Santa Trinita, located on Frescobaldi Square, not far from Piazzale Michelangelo (8, Piazza de’ Frescobaldi).

Day 3: Pisa

One full day in Pisa is enough to admire the most visited landmarks in town, enjoy the local gastronomy, and spend a relaxing time before heading to the next destination. These are the three most remarkable things to do in Pisa in a day.

Pisa is located about 90 kilometers from Florence, getting there by train is fast and easy (from 45 minutes to 90 minutes, depending on the train), while driving can take more time. For more inspiration, be sure to check out our guide on how to get from Florence to Pisa .

Home to the super famous leaning tower, Pisa is one of the most visited towns in the country. Dating back to 1090, the Leaning Tower of Pisa is the main reason why you will visit, and this applies also to all travelers, so head there first thing in the morning to beat the crowds!

The tower is located in the area known as Piazza dei Miracoli (Miracles’ Square) , one of the several UNESCO sites Tuscany. The tower is part of the Pisa Cathedral complex, as it is the cathedral’s bell tower. 

For that reason, in the same area, you will also find the Baptistry of Pisa. All of the buildings were made in the Pisan Romanesque architectural style. The cathedral of Pisa is dedicated to the Assumption of the Virgin.

These religious complexes, often found in many Renaissance squares in Italy, (for instance in Florence) was often made of a trinity of buildings, the Church or Cathedral, the Bell Tower, and the Baptistry.

Piazza dei Miracoli, though, has a fourth structure worth a stop, the so-called Camposanto, the Italian word for cemetery. Pisa’s Monumental Cemetery is a structure made from the same white stone used in the rest of the complex, and it features a picturesque courtyard with dozens of columns that make for spectacular pictures. 

The courtyard also has a beautiful and well-attended garden with dozens of colourful flowers. Inside the main building, there are walls adorned with frescoes which are also worth some time during your visit.

Pisa National Museum and Pisa ’ s Lungarnos

Overshadowed by the popular Leaning Tower, not every visitor is aware of the National Museum of Pisa on the banks of River Arno River.

Several permanent exhibitions host important objects and sculptures related to the history of this important former maritime republic (also known as merchant republics, they were Pisa, Venice, Genoa, and Amalfi).

Also in the museum, there are sculptures from the Pisa Cathedral and its Baptistery.

The museum is located along the bank of the Arno, so after checking out the museum, why not enjoy a relaxing stroll along this important Italian river? 

Several bridges cross the Arno in Pisa, plus several beautiful walks, known as lungarnos. These are the streets of the city that pass beside the river and host wonderful buildings and reach the river outlet in Marina di Pisa. 

These picturesque walks used to be the heart of the city centre where Pisa’s wealthy families would build magnificent homes. The most famous of them all is known as the Lungarno Mediceo.

Day 4: Lucca

Located about an hour and a half from Florence by car (and about the same time by train) , Lucca is a compact town easy to walk around in a day. Down here you can find three unmissable things to do in Lucca during your visit.

Founded on an ancient Etruscan settlement, the city has played a key role in the striving history of the region. To access the old town, it is necessary to pass through one of the many gates located on Lucca’s protective walls.

Mostly dating from the Renaissance, the historic walls of Lucca were erected between the mid-1600s and the early 1800s. The vast fortification over four kilometers long has twelve ramparts and eleven bastions.

And contrary to what you might expect, they were never used for defensive purposes, however, they did have a useful purpose back in 1812 when the gates to the city were closed to prevent the city from flooding… and it worked!

Back in the late 1800s, part of the walls was turned into a public park which is one of the main green areas in Lucca, with dozens of drinking fountains, picnic areas, and games for small children.

Once you pass the gates and enter the ancient district, start by paying a visit to the Romanesque Cathedral of Lucca, built in honor of Archangel Michael. 

Also called San Michele al Foro, this church is a Romanesque masterpiece that was built over an ancient Roman forum, from where it gets its name. The present cathedral was built in 1070, however, it has a more modern facade dating from the thirteenth century.

It is a good idea to climb one of Lucca’s two main towers to have a different perspective of the city centre. The Guinigi Tower is a bizarre tower that hosts a garden of oaks on its top. 

The highest tower in Luca, the Clock Tower features 207 wooden steps and one of the most interesting things to do in Lucca is to climb and admire the clock’s ancient manual mechanism.

Lucca was also the birthplace of the great Giacomo Puccini, often depicted as the greatest opera composer in the country. The Puccini Museum is set in the house where he was born and where he lived before moving to Milan.

Day 5 in Tuscany: Siena

It is not easy to choose only three things to do in Siena , as there is so much to discover in this fantastic Medieval Tuscan city, so I will try to fit a few more options for you to choose from.

We could easily say that the most important places to see in Siena, a UNESCO World Heritage Site, are located between Piazza del Campo, the city’s main square, and the Cathedral, or Duomo di Siena, so let’s see all that can be done in the area.

Featuring an original shape that resembles a shell, this Square is a worldwide famous location as it annually hosts (in July and August) one of Italy’s most important events, the horse race known as Palio di Siena, in which ten of the seventeen contrade or city wards of Siena compete.

Around the Piazza, you can see the important buildings in town, including the Palazzo Comunale housing the town hall, and Torre del Mangia, an 87-meter-high medieval tower that at the top offers spectacular 360° views of the city.

The next stop should be Piazza del Duomo, the cathedral square, which hosts, among other things, the famous Siena Cathedral with some impressive treasures, including the crypt, the baptistery, and the Piccolomini Library with incredible frescoes from the early 1500s.

• The Siena Cathedral Complex Pass is excellent value for money to visit all the most important landmarks in Siena. Check prices and availability here.

Dedicated to the Assumption of the Virgin, Siena’s Cathedral is an important example of a Romanesque-Gothic church with a curious use of abundant white and green-black marbles, the symbolic colors of Siena. 

The building was made between the years 1215 and 1263. Its incredible dome, completed a year after the rest of the church has a lantern added by the prominent artist Bernini. The cathedral’s magnificent bell tower has six bells, the oldest of them dating to 1149. 

This curious but interesting Siena museum hosts the collections of the Palio Horse Race. On Sundays, enter the Contrade Museums instead, where the Palio horse race collections are preserved.

• Walking Tour with Duomo or Contrade Museum Visit: This is a great tour that includes access to the Duomo and a walking tour of Piazza del Campo. Check prices and availability here.

It is a good idea to walk along the well-known Francigena Street to admire the city’s most important buildings and monuments. Here you can stop for a snack and a drink, do some shopping, and enjoy the views of two of Siena’s historic sites.

The first of them is Monte dei Paschi, the oldest bank in Europe and the second oldest bank in the world. It was founded in 1472. 

The other one, Palazzo Tolomei is one of the finest Italian Gothic palaces which was built between 1270 and 1275 by a local family and it as the first permanent headquarters of the Siena Municipality, before the current town hall, Palazzo Pubblico, was built.

Day 6 in Tuscany: San Gimignano

As your Tuscan adventure draws to its closure, day six shelters a magnificent medieval gem, the imposing walled city of San Gimignano, another UNESCO World Heritage site. 

The city, built over a former Etruscan settlement, is small and easy to walk, allowing you to see the main landmarks in just a day.

San Gimignano is known for its incredible Medieval skyscrapers and medieval architecture which gained it the name of the Town of Fine Towers. 

Today, it is possible to observe, as you approach the city from the distance, a characteristic skyline made of twelve well-preserved towers and houses enhanced by the location of the settlement on top of a hill and surrounded by defensive walls.

The tallest tower in town is known as Torre Grossa, with an imposing 54-meter height, this is one of Tuscany’s most important medieval towers, dating back to 1310. 

Surrounding the area, there are several interesting churches to visit, including the city’s Cathedral and several Gothic chapels.

• Torre Grossa and Duomo Tickets: These tickets include entrance to the tower and San Gimignano’s main cathedral. Check prices and more information here.

There is no better place in San Gimignano than this square to get a complete view of what the city would look like during the Middle Ages. 

Right in the heart of the historic center, Piazza della Cisterna is a small square that has a bizarre triangular shape and from where the most remarkable towers in town can be seen, including the remains of an ancient tower on Tortoli Palace, the high Devil’s Tower, and the twin Ardinghelli towers.

From the square, it is possible to walk along via del Castello, an ancient road hosting more Medieval noble homes and typical San Gimignano towers.

No…! This is not a city or a district in San Gimignano, but its most important local product, a fantastic wine.

In fact, San Gimignano is also a perfect gastronomic destination and it is known in the rest of the country for being home to one of the most remarkable wines made in Tuscany (and the rest of Italy), Vernaccia di San Gimignano. 

This white wine is produced from an ancient grape that has strived in the area for hundreds of years, growing on the sandstone hillsides of the area. Other important regional products are San Gimignano’s ham and the locally produced saffron.

Be sure to finish your day in San Gimignano by indulging in an Italian favourite pastime, the Italian aperitivo . This tradition typically sees you having a drink (usually a Spritz) with snacks before dinner together with friends and family and is seen as a way of ‘opening up your appetite’.

As your Tuscany itinerary comes to an end, devote your last day to enjoying the best of the Tuscan countryside and head to the heart of the Chianti region, close to the province of Siena, even when its official borders have never been defined.

Given that wine tasting will be the main activity of your day, the best thing you can do today is to avoid driving from one winery to the next, and join a tour that includes transport. 

Italian road fines tend to be high and severe for those driving and drinking, so let a professional driver take care of the roads while you take care of the grapes!

The following wine-tasting tours of the Chianti region are excellent value for money and have ravishing reviews, check them out:

• Chianti Wineries Tour with Food and Wine Tasting: This original tour is among the top-rated experiences in Tuscany, it includes a visit to two authentic wineries in the beautiful Chianti Hills. Check prices and availability here.
• Montepulciano Wine Tasting and Cellar Tour: A perfect opportunity to taste Montepulciano wines as well as other regional produce from Tuscany. During the trip, you will also learn about the local winemaking traditions and even visit a cellar. Check prices and availability here.
• Full-Day Brunello Wine Tour with Full Lunch: Departing from Florence, this tour takes you to visit to the land of the famous Brunello di Montalcino, discover cellars and taste wines and extra virgin olive oil. It includes a delicious lunch. Check prices and availability here.
• Truffle Hunting and Meal at a Winery: Tuscany is also the region where you can find the best truffles in the country, and this tour proves it. You will join a wonderful truffle hunting experience with a professional guide and dogs. The experience ends with a gourmet truffle lunch at the winery. Check prices and availability here.

Endless are the experiences you can live during a whole week in Tuscany, simply plan your trip and get ready to taste some of the best flavours in Italy.

Enjoyed reading how to spend one week in Tuscany? Pin this article now, read it again later:

Gabi Ancarola is a journalist and travel writer who has lived over 20 years in Italy, and has been living in Crete for the last five years. She hosts culinary tours, translates and writes for her Crete travel blog The Tiny Book . She’s written for Greek Reporter and published several travel guides about Greece.

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Unique 8 days in Tuscany Adventure

• In-depth Cultural
• Food & Culinary
• Local Living
• Partially Guided

• Introduction
• Day 1 Saturday: Collection from Florence Train Station, Welcome at the new Tuscany Home
• Day 2 Sunday: Discovering Arezzo and Anghiari
• Day 3 Monday: Exploring San Gimignano and Volterra
• Day 4 Tuesday: Free
• Day 5 Wednesday: The Chianti Region
• Day 6 Thursday: Hot Springs, Montalcino, Val D'orcia
• Day 7 Friday: Siena and Monteriggioni
• Day 8 Saturday: Drop off at Florence train Station

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Operated by Tuscany Untouched Tours

Tuscany Untouched Tours is a unique travel experience agency that focuses on offering visitors to the Tuscan region an opportunity to explore this beautiful area of the world as local under the expert guidance of Matteo who were born and raised in Tuscany. Our tours and experiences are designed to take you off the well-trodden tourist tracks into areas of Tuscany that many tourists simply don’t get a chance to see. With our tours or Vacation Packages, we take you deep into the heart of Tuscany to meet the locals, experience life as it truly is, and explore areas of natural beauty that will take your breath away. Our mission is to surprise and delight our guests, and deliver a unique experience so magical they won’t want to leave.

Customer Reviews

• Overall Rating Good 3.7
• Itinerary Excellent 4.3
• Guide Average 3.0
• Transport Good 4.0
• Accommodation Good 3.7
• Food Good 3.3
• Tour Operator Tuscany Untouched Tours 4.2
• AC Alexander · 17th October 2022 Tuscany tour: Bad, very bad, the worst ever! We have just returned from a three-week trip to Italy, one week of which was spent with one of your tours entitled “Unique 8 days in Tuscany Adventure with a local” provided by Tuscany Untouched Tours, and I... Show more Trip date: September 2022
• RB Regan · 10th October 2019 I spent 35 days in Italy and this was the best. Trip date: September 2019

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15 Best Tuscany Wine Tours & Wine Tastings for 2024

Thinking About Visiting Tuscany in 2024? Book Some of the Best Tuscany Wine Tours to Experience the Region Like a Local

Italy has been a popular destination for #Winetravelers this year. We’re frequently asked how to best navigate popular regions such as Tuscany , and there really is no better way to fully immerse yourself in the region than by using a guided wine tour or tasting experience that’s operated by a local. With insider knowledge, not worrying about planning, logistics or driving, you can have a much more fulfilling time exploring the region, and usually save yourself a lot of stress and time.

RELATED: Table for Two in Tuscany: Romantic Itinerary for Places to Eat, Stay, Drink & Explore

All of that being said, we’ve compiled a list of the top wine tours in Tuscany based on reader feedback and ratings. These tours include both group experiences, as well as options for private wine tastings and excursions throughout Tuscany. Whether you’re staying within the Tuscan countryside or you’re looking for a day trip from Florence , Rome or Siena , we have you covered below.

Note that for a limited time, we’ve partnered with Viator to provide our readers with secure advanced booking, free cancellation as well as an exclusive 15% discount on any wine tours that are booked via Winetraveler.com . Simply use code WINETRAVELER15 at check out.

RECOMMENDED: Stay at These Luxury Tuscan Vineyard Resorts While You Visit Tuscany

Horseback Ride and Poolside Day Chillout with Tuscan Lunch

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Florence serves as an ideal base for Tuscany wine tours due to its central location within the region, providing easy access to renowned wine areas such as Chianti, Montepulciano, and Montalcino. Its well-connected transportation system, including train routes and bus lines, ensures hassle-free travel to various vineyards and wineries.

RELATED: The Best Tuscany Wineries, Hotels & Vineyard Resorts to Experience

Additionally, numerous tour operators within Florence offer curated wine experiences that cater to a range of preferences, from small boutique wineries to larger renowned estates. This, combined with the city’s own rich cultural and culinary scenes, makes Florence the perfect starting point for exploring Tuscany’s wine country.

Tuscan Safari: Tuscan Villas with Vineyards, Cheese, Wine & Lunch from Florence

Winetraveler Rating (over 2,213 reviews):

Italy’s iconic Tuscany region is more than just a destination – it’s a feast for all your senses. This full-day Tuscany wine and food tour, departing from Florence, offers you the chance to taste the region’s finest offerings, guided by experts with in-depth local knowledge.

Navigate the enchanting Tuscan countryside in a comfortable 4×4 minibus, stopping to explore a historic wine estate and villa, and a cellar filled with delectable Chianti Classico. Each stop on your journey is an opportunity to learn more about wine and olive oil production, and to indulge in locally-sourced cheese and other Tuscan delicacies.

This unique journey culminates in a traditional 3-course Tuscan lunch at a winery restaurant with breathtaking views. Experience the magic of the Chianti region as you dine amidst vineyards under the Tuscan sun.

This particular tour, operated by Walkabout Tours, has been designed to ensure a seamless and enriching experience for our #Winetravelers.

Highlights:

• Full-day wine and food tour from Florence, with 4×4 off-road minibus transportation.
• Traverse the scenic Tuscan countryside on an off-road adventure.
• Delight in a traditional Tuscan lunch at a picturesque winery restaurant.
• Explore a historic wine estate, with a guided tour of wine, extra-virgin olive oil, and cheese tastings.
• Visit a second winery for a deeper dive into the renowned Chianti Classico wine.

15% Off With Code WINETRAVELER15

Florence Vespa Tour: Tuscan Hills and Italian Cuisine

Winetraveler Rating (over 2,165 reviews):

Venture off the beaten path and explore the heart of Tuscany on a classic Vespa scooter. This unique tour, offered by Walkabout Tours, takes you on a scenic ride through the Tuscan hills, starting from the Renaissance city of Florence. With a knowledgeable local guide leading the way, you’ll discover hidden gems such as the Piazzale Michelangelo and the Church of San Miniato al Monte.

RELATED: 25 Best Things To Do in Florence Italy: Visitor’s City Guide

The adventure doesn’t end there. After exploring the picturesque countryside, head back to a welcoming country estate to indulge in a delicious traditional Italian meal. Feast on a menu of mouth-watering bruschetta, perfectly cooked pasta, and a flavorful cheese and salami board. Experience the authenticity of Tuscany as you dine surrounded by its natural beauty.

To ensure a truly personalized and intimate experience, this tour is limited to 15 travelers.

• Explore the Tuscan hills on your own Vespa scooter, led by a local guide.
• Discover lesser-known sights such as the Piazzale Michelangelo and the Church of San Miniato al Monte.
• Delight in a traditional Tuscan meal at our country estate, featuring local favorites like bruschetta, pasta, and a cheese and salami board.
• Enjoy the personalized attention offered by small-group tours with a maximum of 15 participants.

This Vespa tour in Tuscany, presented by Walkabout Tours, gives you a unique opportunity to experience Tuscany’s charming countryside in an authentic and memorable way. Don’t just visit Tuscany, live it like a local!

Grab this opportunity to explore Tuscany in the most Italian way possible. Reserve your spot now as this is one of the best selling Tuscany wine tours currently.

Tuscany Bike Tours: One Day Bike Tour through the Hills of Tuscany

Winetraveler Rating (over 1,158 reviews):

Escape the bustling city of Florence and immerse yourself in the natural splendor of the renowned Tuscan countryside. Offered by Tuscany Bike Tours, this top-rated bike tour combines the awe-inspiring scenery of Tuscany, a rich history that spans centuries, and an authentic taste of the region’s flavors in an exciting and active way.

Pedal across fertile valleys and hilly landscapes adorned with olive trees and vineyards, stopping to explore a 12th-century villa and indulge in a traditional Italian restaurant for a mid-day meal. Recharge and enhance your journey with tastings of Chianti wine and local olive oil – the signature flavors of Tuscany.

• Cycle through the beautiful Tuscan countryside, leaving the city behind.
• Enjoy a wine tasting at a medieval castle and savor a delectable lunch at a local restaurant.
• Engage in an active and refreshing journey, a welcome alternative to being confined on a bus.
• Join the ranks of satisfied travelers who’ve showered this bike tour with hundreds of 5-star reviews.

Experience the Tuscan region in a refreshing and dynamic way. The inviting landscape, the ancient history, the flavors of the region – all come together on this journey to provide an unforgettable Tuscan experience.

Ready for the ride of a lifetime? Secure your spot on this Tuscany Bike Tour today.

Pizza and Gelato Cooking Class at a Tuscan Farmhouse from Florence (with wine, of course)

Winetraveler Rating (over 3,633 reviews):

Embark on a delightful culinary adventure near Florence, nestled within a picturesque Tuscan estate. Ideal for culinary enthusiasts and culture lovers, this unique experience allows you to learn the art of crafting two of Italy’s culinary treasures – pizza and gelato, guided by a professional Italian chef.

This interactive, hands-on cooking lesson culminates in a delicious 3-course feast of appetizers, freshly made pizza, and delectable gelato, all paired with a selection of fine wine and beer. To keep the magic of this culinary adventure alive, you’ll also receive a recipe booklet to take home and hone your new skills.

• Participate in a pizza and gelato cooking lesson, right in the heart of Tuscany.
• Learn the art of crafting two iconic Italian delights under the guidance of a professional chef.
• Relish a 3-course meal accompanied by wine or beer, all set within a charming Tuscan estate.
• Enjoy round-trip transportation from central Florence for a hassle-free experience.

Why Choose this Tour? This gourmet cooking class pairs two beloved Italian classics with the unbeatable scenery of Tuscany, creating an immersive experience that surpasses any restaurant setting.

Ready to create some delicious memories? Book this culinary adventure now and add a slice of Tuscan flavor to your journey. Unleash your inner chef and bring a piece of Italy back home with you.

Tuscan Wine Tour with Lunch, Visit to San Gimignano & Organic Wineries

Winetraveler Rating (over 547 reviews):

Take a break from the energetic pace of Florence and set off on a journey into the heart of the Tuscany wine region. This day trip includes round-trip transport from a central Florence location, making your adventure as comfortable as possible.

In the company of your knowledgeable guide, you’ll gain valuable insights into the intricate winemaking process at local vineyards, typically overlooked by many visitors to Tuscany. The day’s schedule is thoughtfully designed to include wine tastings, an authentic Tuscan lunch, and ample opportunities for capturing beautiful photographs against the backdrop of Tuscany’s scenic landscapes.

• Savor tastings of Chianti wines and relish a traditional Tuscan lunch.
• Benefit from the expertise of a guide, ensuring a stress-free exploration without the need for navigation.
• Gain insights into the winemaking process unique to the Chianti region.
• Enjoy hassle-free, round-trip transportation from a central Florence location.

Discover the serenity and charm of Tuscany’s renowned wine region with this insightful Chianti day trip. Immerse yourself in the winemaking heritage, savor authentic Tuscan cuisine, and capture memories set against Tuscany’s breathtaking vistas.

Ready to uncork the magic of Tuscany & Chianti? Book this day trip now and delve into a world where the essence of Tuscany comes alive in every vineyard, every glass of wine, and every plate of food.

Self-Drive Vintage Fiat 500 Tour from Florence: Tuscan Wine Experience

Winetraveler Rating (over 415 reviews):

Embark on an Italian adventure like no other as you couple a wine tasting experience with a classic Fiat 500 tour. Departing from Florence, step into the driver’s seat of a beautiful 1960s Fiat 500 model, and journey through the Tuscan hills as part of a scenic convoy. The tour reaches its crescendo as you park your vintage ride at a stunning 15th-century wine estate and villa.

• Enjoy a self-driven Fiat 500 tour from Florence, highlighting the esteemed wines of Tuscany.
• Visit a captivating 15th-century Renaissance villa and wine estate nestled in the Tuscan countryside.
• Immerse yourself in the estate’s vineyards and cellars, indulging in tastings of several locally produced wines.
• Travel through the scenic Tuscan hills with confidence, guided every step of the way.

Explore the splendors of Tuscany in an unforgettable way. From the thrill of driving a classic Fiat 500 through the picturesque hills, to the rich taste of Tuscan wines in a historic setting – this tour promises a feast for the senses.

Ready to drive into a day of Tuscan delights? Reserve your spot now and create memories that will last a lifetime.

Private Tuscany Wine Tour Experience from Florence

Winetraveler Rating (over 54 reviews):

Delve into the heart of Tuscany’s world-renowned flavors and stunning landscapes on a private wine tour from Florence. Journey through the picturesque hills and vineyards in the company of a knowledgeable sommelier guide, visiting three distinctive estates to sample top-notch regional wines and olive oil.

The journey includes a visit to a family-owned winery, where a traditional Tuscan lunch, paired with an array of fresh local products and wine, awaits you. Gain insights into traditional winemaking processes through a cellar tour and engaging conversations with winemakers.

• Full-day private wine tour from Florence, removing any uncertainty about selecting wineries, thanks to your expert sommelier guide.
• Explore three diverse wineries, including quaint family-run and organic estates.
• Discover the winemaking process through an immersive cellar tour.
• Savor a range of the region’s best varietals.
• Enjoy an authentic Tuscan lunch crafted from locally produced ingredients.
• Benefit from the flexibility to tailor your itinerary to your preferences.

Embark on a journey of flavor and beauty in the Tuscan region. From the quaint charm of family-run vineyards to the vibrant taste of Tuscan wines and the warm hospitality of the locals, this tour promises a truly enriching experience.

Winetraveler Rating (over 15 reviews):

Trade the bustling streets of Florence for a day of tranquility immersed in nature. Experience a horseback riding adventure through the picturesque Tuscan countryside, capped off with downtime at an elegant country resort nestled within the verdant Florentine hills. Indulge in a delightful Tuscan lunch served poolside and complemented by local Chianti wine.

• Escape the crowds of Florence and embrace the tranquility of the Tuscan countryside.
• Absorb the lush landscapes from the unique perspective of horseback riding, suitable for all levels.
• Enjoy a private experience tailored exclusively for your party.
• Benefit from round-trip transfers from Florence for a hassle-free day.

Immerse yourself in the calming serenity of Tuscany’s nature. From the thrill of horseback riding through picturesque landscapes to relaxing at an elegant resort with a refreshing poolside lunch, this day promises a rejuvenating escape from the hustle and bustle.

Tuscany Wine Tours from Rome

While Rome is not located in Tuscany, its position and connectivity make it a viable alternative base for Tuscany wine tours. Rome’s strategic location allows for comfortable day trips to southern Tuscan areas like Montepulciano and Montalcino, both renowned for their exceptional wines. The Italian capital boasts excellent high-speed rail links and highway networks that can transport you to the heart of Tuscany in just a couple of hours. This flexibility allows you to explore Tuscany’s world-class vineyards and return to Rome’s vibrant nightlife and historical attractions all in one day, offering a rich, balanced travel experience.

Tuscany Wine Tour from Rome with Private Driver

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Make the most of your time with this private tour that covers three enchanting hill towns in Tuscany and Umbria in just one day. With the convenience of hotel pickup in Rome and a full day’s transport, you can indulge in wine tasting in Montepulciano, savor the renowned pecorino cheese in Pienza, and admire the breathtaking views from the cliffside town of Orvieto.

• Benefit from round-trip private transportation from your hotel or chosen location in Rome.
• Enjoy ample free time to explore and shop in the beautiful towns of Montepulciano, Pienza, and Orvieto.
• Experience the unique flavors of Tuscan wines, cheeses, and other gourmet delights.
• Take advantage of a private day trip for greater flexibility and personalized attention.

Embark on a journey through the scenic landscapes of Tuscany and Umbria. Savor the exquisite flavors of the region, marvel at the panoramic views, and soak up the unique charm of these picturesque hill towns.

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Trace the footsteps of the Etruscans as you visit the picturesque medieval settlements of Montepulciano and UNESCO–listed Pienza, two of Tuscany’s most charming hilltop towns. Starting from Rome, this tour offers a comfortable journey in an air-conditioned minivan, giving you ample time to explore the historical streets at your own pace. Revel in the magnificent panoramas over the Val d’Orcia, with round-trip transport from your Rome hotel included.

• Explore the enchanting towns of Montepulciano and UNESCO–listed Pienza in a single day.
• Enjoy ample free time to discover the rich history and culture of these sites at your own pace.
• Be captivated by the panoramic views of the Val d’Orcia from the vantage point of Pienza.
• Benefit from round-trip transportation in an air-conditioned minivan from your Rome hotel.

Step back in time and explore the medieval charm of Tuscany. From the Etruscan roots of Montepulciano to the UNESCO-listed beauty of Pienza, this tour offers a captivating look into Tuscany’s past.

Tuscany Wine Tours from Siena

Tuscany hiking tour from siena including wine tasting.

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Join us as we step back in time, tracing the footsteps of ancient pilgrims along the Via Francigena, a historic route that connected Canterbury, England, to Rome. This rural path winds through charming villages, vineyards, and some of Tuscany’s most picturesque landscapes. The journey concludes in the enchanting medieval village of Monteriggioni, where you’ll be rewarded with a curated wine tasting. To wrap up your adventure, we’ll provide a train ticket for a comfortable return to Siena.

RELATED: Here’s Why You Should Include Siena on Your Next Trip to Italy

• Enjoy a half-day hiking tour from Siena coupled with a delightful wine tasting.
• Follow sections of the historic Via Francigena, a key pilgrimage route leading to Rome.
• Absorb the history of the route from our expert guide.
• Traverse between Siena and the medieval walled village of Monteriggioni.
• Bask in the captivating Tuscan vistas of rolling hills blanketed in vineyards and olive groves.
• Immerse yourself in local flavors during an educational wine tasting session in Monteriggioni.
• Take advantage of the included train ticket for a convenient return to Siena.

This is more than just a hike; it’s an invigorating journey through history and a celebration of Tuscany’s beautiful landscapes and rich flavors. Ready to walk the ancient paths and savor the local wines? Book your spot today!

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Tuscany is famed worldwide for its exceptional wines. Get an insider’s view into this illustrious industry with a tasting tour in the vineyards close to Siena. This intimate tour, limited to just 12 participants, takes you to a historic cellar where you’ll refine your palate and learn to distinguish delicate flavors under the guidance of a sommelier. With a choice of morning or afternoon departure, you can conveniently fit this experience into even the most packed sightseeing agenda.

• Break away from the city and effortlessly explore the vineyards surrounding Siena.
• Sharpen your palate to discern subtle flavors under the guidance of a trained sommelier.
• Choose from two departure times throughout the day for your convenience.
• Benefit from personalized attention in a small group limited to 12 participants.

Unleash your inner wine connoisseur on this exclusive tasting tour. From exploring historic cellars to learning from a knowledgeable sommelier, this experience brings you closer to Tuscany’s rich wine culture.

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Experience the unique thrill of hunting for Italy’s coveted tubers in the Tuscany countryside during an authentic truffle hunt near San Miniato. Join Francesca, a seasoned forager, and her truffle-hunting dog for a leisurely stroll through the woods in search of fresh truffles. After the hunt, unwind at her family farmhouse, where a mouth-watering lunch featuring the day’s truffle harvest awaits.

• Engage in the age-old tradition of truffle hunting with an experienced local “tartufaio” in Tuscany.
• Enjoy a walk through the woodlands near San Miniato with a specially trained truffle dog.
• Relish a satisfying lunch featuring bruschetta and pasta adorned with freshly found truffles, followed by dessert.
• Enjoy the warmth of local hospitality during this immersive experience at a family-run farm.

Embark on a truly unique Tuscan journey. From the exciting pursuit of truffles to the exquisite flavors of a truffle-infused lunch, this experience offers a deep dive into the tradition and culinary richness of Tuscany.

Tuscany Travel Logistics

Getting to tuscany.

Florence Airport, Peretola (FLR): Known as Amerigo Vespucci Airport, it’s the closest airport to the heart of Florence and Tuscany. It’s relatively small and offers fewer international connections, but it’s a popular choice due to its proximity to Tuscany’s major cities. Browse current flight deals and book as the best rates arise using Kayak.

Pisa International Airport (PSA): Also known as Galileo Galilei Airport, this is the largest airport in Tuscany with more international flight connections. Pisa airport is well-connected to Florence and other Tuscan cities by both train and bus services.

Bologna Guglielmo Marconi Airport (BLQ): Although not located within Tuscany, it’s another good option to consider as it has strong flight connections, both domestic and international. It’s roughly an hour and a half’s train ride to Florence.

RECOMMENDED: Visit Cinque Terre: Wine Tasting Itinerary & Travel Guide For Wine Lovers

Arriving from Other Parts of Italy

Tuscany is well-served by Italy’s extensive train network. The high-speed trains from cities like Rome, Milan , and Venice make getting to Tuscany both quick and convenient. Florence’s main station, Firenze Santa Maria Novella, is a major hub connecting Tuscany to the rest of Italy.

Getting Around Tuscany

Public transportation.

Trains: The train network in Tuscany is quite extensive, connecting not only the major cities but also smaller towns. They are generally punctual, affordable, and efficient.

Buses: For some of the smaller towns and villages, bus is the only public transport available. Although they can be less predictable than trains, buses can get you to places trains can’t reach.

Renting a car can be an excellent option if you wish to explore the countryside or visit vineyards at your own pace. Do remember that driving in Italy requires an International Driving Permit along with your regular driver’s license for non-EU citizens. Also, many city centers in Tuscany are limited traffic zones (ZTLs) and are camera-controlled. Driving into these zones without a permit will result in a fine.

Taxis are readily available in cities and larger towns. Uber operates in Florence and is another convenient option for getting around.

Best Time to Visit: Tuscany is a year-round destination, but the ideal times to visit are between April and June, and September and October when the weather is comfortable and the countryside is at its most vibrant.

Language: Italian is the official language. However, English is widely spoken in tourist areas, hotels, and restaurants.

Currency: Euro (€) is the official currency of Italy.

Safety: Tuscany is generally safe for tourists, but like any other tourist destination, be aware of your surroundings, particularly in crowded places.

Electricity: Italy operates on a 220V supply voltage and 50Hz. The power plugs and sockets are of type F and L.

Cities, Towns and Villages within Tuscany

As the capital of Tuscany, Florence is an incredible mix of art, history, and culture. It’s the birthplace of the Renaissance, and home to world-class museums such as the Uffizi Gallery and the Accademia Gallery, where you can admire Michelangelo’s David. The city also has a rich culinary scene, with countless trattorias serving classic Tuscan cuisine. Florence is an ideal base for day trips throughout the region, thanks to its central location and excellent transportation links.

Famous for its medieval cityscape and the historic Palio horse race, Siena is a must-visit. The city’s heart is the Piazza del Campo, a shell-shaped square that hosts the Palio twice every summer. The Siena Cathedral (Duomo di Siena) is another highlight, featuring intricate Gothic architecture. Siena’s historical center has been declared a UNESCO World Heritage Site for its preserved medieval city planning and architectural splendor.

RELATED: Top Small Towns in Italy to Visit Famous for Wine [Wineries & Wine Tour Options Included]

Known worldwide for its leaning tower, Pisa has much more to offer. The city hosts a wealth of historic sites, including the Piazza dei Miracoli, where you’ll find the Leaning Tower, the Pisa Cathedral, and the Baptistery. For an authentic Tuscan experience, visit during June when the city celebrates the Luminara di San Ranieri festival with thousands of candles lighting up the riverside.

Enclosed by well-preserved Renaissance walls, Lucca is a charming town ideal for leisurely exploration. Its cobblestone streets, beautiful piazzas, and numerous churches, including the Lucca Cathedral, offer a snapshot of its rich history. One fun fact is that the town’s intact city walls have been transformed into a pedestrian promenade, perfect for biking or a leisurely walk.

San Gimignano

Known as the “Town of Fine Towers”, San Gimignano is famed for its 14 medieval towers that dominate the skyline. This UNESCO World Heritage Site offers fantastic art, great dining, and world-class gelato at the Gelateria Dondoli, a two-time champion of the Gelato World Cup. Its proximity to Chianti makes it an excellent stop on a Tuscan wine tour.

Montepulciano

This medieval and Renaissance hill town is known for its Vino Nobile wines. Stroll along the Corso, a grand avenue packed with Renaissance palazzi and churches, or visit the impressive Tempio di San Biagio. The town also offers panoramic views over the surrounding vineyards and Val d’Orcia.

Best known for its Brunello di Montalcino wines, this hilltop town is a favorite among wine lovers. Besides its wine, the town boasts a stunning fortress offering panoramic views, a charming historical center, and the beautiful Romanesque Abbey of Sant’Antimo.

RELATED: Read Recent Articles and Travel Guides for Exploring Italy

A true hidden gem, Volterra offers Etruscan, Roman, and medieval sites, including the Roman Theatre and the Etruscan Acropolis. Volterra is also renowned for its alabaster craftsmanship, a tradition that dates back to the Etruscan period.

Set on a hill overlooking Lake Trasimeno, Cortona is one of Tuscany’s oldest towns with a history dating back to the Etruscans. Visit the Museo dell’Accademia Etrusca, or explore the town’s charming narrow streets and squares. The town is also known from the book and movie “Under the Tuscan Sun.”

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Frequently Asked Questions about Wine Tours in Tuscany

What kinds of tuscany wine tours and wine tasting experiences are there.

Tuscany offers a rich variety of wine tours and tastings that cater to all tastes and preferences. For instance, there are full day private tours from Florence, led by a knowledgeable sommelier, offering the chance to visit three different wineries and enjoy an authentic Tuscan lunch. For those looking to combine scenic drives with wine, consider the excursion that pairs a Fiat 500 tour with a visit to a 15th-century wine estate. Alternatively, you can delve into Siena’s surrounding vineyards on a small group tasting tour that educates your palate with the help of a sommelier. For those seeking a unique countryside experience, a horseback riding tour in the Tuscan countryside lets you unwind at a country resort with a full Tuscan lunch and local Chianti wine. These are just a few examples of the range of experiences Tuscany has to offer. Each tour provides a unique way to explore the region’s world-renowned wine culture. To learn more and book a wine tour that suits your preference, please check our detailed guide.

When is the best time of year for a wine tour in Tuscany?

The best time to visit Tuscany for a wine tour largely depends on your personal preferences, but there are a few peak periods that are particularly popular. Spring (April to June) and Fall (September and October) are often considered the ideal times for a Tuscan wine tour. The weather during these seasons is typically mild and pleasant, and the landscape is at its most vibrant – with blooming flowers in spring, and changing leaves in the fall. Fall is also the time of the grape harvest (known as “vendemmia”), which can be a fascinating process to witness. Some wineries even allow visitors to participate in the harvest. Summer (July and August) in Tuscany can be quite hot, and many Italians go on vacation in August, which means some wineries might be closed. However, the region is still beautiful during this time and the wine tours are certainly still operational. Winter (November to March) is the low tourist season in Tuscany. While the weather can be cooler and wetter, there are fewer tourists, making it a good time to visit if you prefer to avoid crowds. Regardless of when you choose to visit, it’s always a good idea to check with individual wineries or tour companies in advance for their operating hours and to book your tour.

What is the main wine region in Tuscany?

The most renowned wine region in Tuscany is the Chianti region, famous for producing Chianti and Chianti Classico wines. It’s characterized by its idyllic rolling hills, historic vineyards, and scenic villages. The Chianti region is situated between Florence and Siena, making it conveniently accessible for tourists and wine lovers. However, Tuscany boasts several other notable wine-producing areas. For example, Montalcino, located south of the Chianti region, is renowned for its Brunello di Montalcino wines. Nearby, Montepulciano produces the famous Vino Nobile di Montepulciano. Further west towards the coast, you’ll find the Bolgheri region, known for its superb “Super Tuscan” wines, a term referring to high-quality wines that don’t adhere to traditional Italian wine regulations but have nonetheless achieved worldwide recognition. Each of these areas offers unique variations in climate, soil, and winemaking traditions, contributing to the diversity and richness of Tuscan wines.

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A Tuscan Food & Wine Tour in Florence (the Perfect Dinner Experience)

I f you’re looking for a unique experience in Florence, far from the maddening crowds of the Duomo, you’ll find exploring the charming cobblestone streets of a lively Florentine neighborhood on a Tuscan food and wine tour a highlight on your trip!

Travel is not just checking of bucket list items – although one cannot miss the magnificence of the Statue of David – it’s also about diving into the heart of local culture through its culinary delights.

If you’re not familiar with Tuscany’s food and wine, then don’t try and do it all on your own. At least carve out a few hours of your time in Florence to join a food walking tour so you can really learn to understand the importance of Tuscan cuisine and wine and how it’s evolved from the food of the poor to one of the most sought-after cuisines in the world!

We had done a previous food tour in Paris and street food tour in Rome, which involved lots of walking and many short food stops.

However, the sunset food and wine tour in the Oltrarno neighborhood in Florence was at a more relaxed pace.

We had fewer stops, more time to chat over Florentine steak and glasses of Chianti ( which this region of Italy is well-known for) and learned so much from our knowledgeable tour guide.

I loved it just as much as our other food walking tours and I was so glad we had the opportunity to see this side of Florence.

But if you’re thinking about dining out Florentine style but you’re not sure what to expect, this guide will tell you all about our experience on a Tuscan food & wine tour and how you can go about one yourself.

We joined the Oltrano food and wine tasting tour in Florence. You can check prices, availability, and more reviews by clicking this link.

Where To Do A Tuscan Food and Wine Tour? The Oltrarno Neighborhood of Florence

What to expect on a tuscan food and wine tour, about our local florentine guide on food tour in florence, 1: wine tasting and florentine focaccias, 2: the famous wine windows, 3: wine and cured meats , 4: florentine steak & vin santo at trattoria bbq, 5: original gelato at gelateria artigianale la sorbettiera, is this food and wine tour in florence suitable for kids, is this suitable for those with dietary requirements, where does this food and wine tour of florence meet, do you visit the wine cellars on a food and wine tour in tuscany.

Before we jump into what you can expect from the tour, let’s quickly introduce you to the foodie neighborhood. The Oltrarno neighborhood is just over the Arno River, south of Florence city center. Its name actually means, “on the other side of the Arno.”

It’s gaining popularity lately as a place to visit on your Florence trip for a more local and quieter experience. And it’s known to be one of Florence’s liveliest and most authentic neighborhoods, a little similar to Trastevere in Rome, although possibly not as busy.

In this neighborhood you’ll find craft shops, antique stores, tranquil squares, great restaurants, wine bars (enotecas) and other wonderful attractions like Pitti Palace, Boboli Gardens and Villa Bardini. And it’s where many come for spectacular sunset views from Piazzale Michelangelo. This post on how to spend a day in Oltrarno will help you plan for these amazing experiences. We loved dedicatitng almost an entire day in Oltarno on our Florence two day itinerary.

But we weren’t experiencing those Florence attractions on this tour; we were here just for the food and the wine.

Although we only visited five stops on this food tour, we had over eight food tastings and four drinks on our food and wine tour. Not only that, but we visited only family-run, small businesses, so we felt good about contributing to the local economy.

We had not only Florentine Steak, but aperitifs and dessert, so our bellies were full come the end.

As well as savouring the delights of Tuscan food and wine, you can also expect to learn a lot about Tuscan eating habits, traditions, history, and where the food and wine comes from.

We didn’t do any winery visits on this tour, but we did sample plenty of wines!

We met with Chiara, our guide who is a born and bred Florentine in the Piazza Santo Spirito, an area popular with locals for socializing during aperitivo hour under the shade of the beautiful church.

Chiara brought together our small group of ten under the one term of “family.”

“ Okay family it’s time to eat. Allora family, let me tell you about…. “

I loved how one word made us feel like we were a part of something special. I’ve found myself saying it several times to my own family as we continued our travels across Italy.

Chiara has been a guide for several years and understands well the importance of Tuscan food and how it is different to the rest of Italy.

As we learned on our food tour of Rome , there aren’t really national dishes in Italy, as each region has had a long history of their own style of cuisine using regional ingredients long before Italy became the country that it is now.

Chiari also began by having us introduce yourself and share our favorite food in Italy (another cool way to help us connect on this more social tour)

We weren’t allowed to say all of it, but all of us had some version of pizza or pasta – none of which come from Tuscany!

Tuscan food is based on bread and meat, not pastas and pizza so common across Italy. (This doesn’t mean you won’t find it in the restaurant in Florence!) And with that we were ready to begin this unique dinner experience in Florence.

Stops on The Food and Wine Tour in Florence

As is typical of a Devour food tour , we were visiting local family run establishments – five stops including Florentine Steak and enotecas, which is Italian for wine. 

Chiara then moved us to our first stop with a simple, “Andiamo Family” – Let’s go!

We didn’t have far to walk, just around the corner to a small enoteca, or wine bar where we crowded around a small table for Chianti wine and Florentine focaccias topped creamy Stracciatella cheese with truffle; bruschetta; and onion and rosemary.

Chiara was very accommodating to my gluten free requirements, bringing me out gluten free crackers and a plate of pecorino cheese with honey and marmalade.

Our first wine for the tour was a 2020 Le Ginestre Sangiovese.

She pointed out the black rooster on the bottle of red wine, which lets you know this is a Chianti classico, which is the original wine from the Tuscany region of Italy between Florence and Siena .

It was declared a wine region in 1716 by Cosimo III de’ Medici, the Grand Duke of Tuscany. 

120 years later, five more chianti areas have been declared. For a wine to label itself with the Chianti DOCG it must contain at least 70% Sangiovese grape, along with small percentages of other varieties.

Tow other popular wines from the Tuscany region are Brunello di Montalcino and Vino Nobile di Montepulciano, which are also made from the same grapes, but we stuck with the Chianti on this tour.

As we learned on this first stop on this Tuscany wine tour, wine in Tuscany is part of the meal. You should never drink Sangiovese outside of meal hours.

To demonstrate this Chiara had us first sip the glass of Chianti classico before we ate anything. Then we had another taste after some of the food.

It was quite remarkable how the flavor profile changed, and the wine tasted better with the food. The oil ingredients of the food balance the acidity of the wine so it bites less. Without food your mouth turns dry.

Without realizing it, this is what I noticed eating at our local restaurant, Giorgio Pizza in Raleigh , when I wrote “The ragu elevated the Sangiovese to another level.”

Ciara told us to “ Mangia mangia” – eat that plate clean – while she told us more about the history of Florence, including the powerful Medici family of Tuscany, and the importance of extra virgin olive oil and how it’s put on everything except cappuccinos.

Once our plates were cleaned, we stood up for our next stop!

I’m sure if you’ve been searching for things to do in Florence , you may have come across wine windows.

Buchette del vino, wine windows are unique to Florence and now a tourist attraction, possibly made famous by all the people sharing the experience on the Gram.

You may have heard lots of versions of how they came about, including because of the plague – and people still need their wine! Sounds like they would have been a perfect fit for COVID. (In fact, I do think they were used for both reasons mentioned, but not their original intention.)

It all began in the 16th Century with the noble families who had vineyards in the Tuscan countrysid e. They saved their good wine for family and friends.

The bad vino? They sold them through these palace windows to commoners in Tuscan fiascos, which are pear-shaped flasks covered in straw. These wine windows saved them from having to open up a shop or pay taxes.

Most wine windows in Florence are about twelve inches high and eight inches wide and with a similar dome shape. There were once about two hundred of them but now there are only a handful operational in Florence. I smell opportunity and wonder why there aren’t more wine windows open for business!

We visited the cute yellow wine window attached to the equally cute and charming Babae restaurant , which was once the palace entry way. There was a lengthy line of tourists, and thankfully being on a guided food tour, you get priority so less waiting time.

It was fun to step up and order, red or white and receive your glass from a hand slowly coming out. The girls got water instead of wine!

We then stood around on the streets soaking up the atmosphere while we chatted more to our fellow travelers, drank a fresh, crisp Tuscan white, and listened to Ciara share more interesting history about the wine windows and noble families.

I’m glad we did this wine window on a tour as I wouldn’t line up for it otherwise – a bit too touristy. We passed by it earlier in the day, around 1pm and there was a line even then.

And Craig and I attempted another wine window near our hotel but left quickly as we couldn’t be bothered lining up that long for a glass of wine. I know I should probably care better, considering we’re travel bloggers, and you know… the gram!

But we’re a little different in that we don’t care more about enjoying the present moment than a chance to go viral. Basically, great at life, not so much at Instagram!

And I really don’t want to increase the waiting time for people behind me by hogging the limelight to get a gramworthy shot. 

As it’s a food and wine tour, it makes sense our next stop was another family-owned small enoteca or wineries. Again, we were following Tuscan rules by drinking wine with our food. This time it was a plate of cured meats.

We had Tuscan salami and prosciutto , which was saltier than others, Tuscan salami with black pepper seeds and Tuscan salami with fennel seeds.

Then an interesting new taste white salami, or Lardo, which is pork fat seasoned with black pepper, juniper sage, and rosemary and six months seasoned so it comes out softer and nicer.

I’m not sure how I felt about this one. I enjoyed trying it, but not sure I’d eat a lot of it.

At this stop on our Florence food tour, we had a glass of white wine which is refreshing for cheers – Salute in Italian , which means good health for yourself and family.

Followed by a 100% Sangiovese grown in the chianti region, but aged less than one year. To be a classico, it must be aged for at least one year.

This Sangiovese is even sharper than the other if drunk on its own, and this Tuscan red tastes better with cured meats.

For this wine tasting exercise, Chiara told us not to eat fennel salami before tasting the wine as fennel seeds change your palette. Serving fennel first was once a sneaky trick used to disguise bad tasting wine, as you won’t taste it!!

But now the secret is out.

That’s a way for you to stomach any bad red wine you may get as a gift or accidentally buy at the store!

As we ate, Chiara shared more about this formerly working-class neighborhood we were sitting in and an exciting event happening the weekend following our visit.

Florence was once divided into four church districts , each represented by a color, and every year they districts play each other in a local sport called Calcio Storico.

This unusual football match is a mix of soccer, wrestling, American football and rugby.

The final is always played on June 24 , Florence’s patron saint’s feast day for St John the Baptist and this year, red (Chiara’s team) were playing blue.

The game originated in the 16th century and is recreated every year including the dirt floor arena in front of Santa Croce.

This is one of the main events of the year in Florence and crowds come out to watch the game, and teams’ parade around in historical costumes and fireworks at night. 

Apart from the wine, we were most looking forward to eating Florentine steak. We were thrilled when we saw it was on the menu. Florentine steak can be expensive, so I was grateful to try it on this food tour!

Chiara led us to the beautiful outdoor seating at Trattoria BBQ . The sun was starting to go down so temperatures were ideal for sitting outside. 

Passionate Florentine, Chiara made sure to let us know the etiquette and laws around cooking and eating Florentine Steak. Like French pastries and wine, this is serious business.

Florentine steak is a T-Bone steak and by law must be 3 – 4 fingers thick and cooked rare or medium rare to about 55°C / 135°F in the middle.

You must not spoil the steak by eating any starters and show up to the table hungry. You can have sides but make them simple. Usually, you’ll share the steak with another person, but if not, drop the sides.

Season the steak only with salt and pepper and cook for one minute on the bottom and top, 6 or 7 minutes on side and then 1 minute standing on top to let the juices flow.

Absolutely no sauces. Chiari feels visibly sick thinking about ketchup on Florentine steak and she asks that you do not offend Florentines by not following her instructions.

I was happy to let the steak do the flavor talking!

Chiara gave us a demonstration of how to eat it by drizzling olive oil on the plate and adding salt and pepper to it. Then you take your pieces of steak and dip it in.

You can pair the steak with Tuscan bread, and most importantly, red wine. Even better if served in a Tuscan fiasco.

Sitting around the table eating delicious Florentine steak, drinking Tuscan red wine, and chatting about life, travel, and more with the other guests on the tour was a highlight. Chiara then bought out a surprise for our group:

A glass of Vin Santo paired with an almond-studded biscotti and a small glass of Vin Santo. Craig and I had some of this dessert wine at our Tuscan farm stay the evening before and I was not jumping out of my skin to have more.

On their own, both are pretty gross – the wine super sweet and the bread biscotti dry and hard.

But together it’s a miraculous example of how two uglies can become beautiful when married at the same time.

I didn’t try the sweet wine with the biscotti during our farm stay. This time, I decided to try just a little bit with the biscotti to see what this was really about (I am gluten free so a little was all I could spare).

I really did enjoy how sweetly moist the biscotti came after a few seconds dipped in the sweet dessert wine. It was actually quite moorish and I had to stop myself from continually dipping.

This is a traditional Tuscan dessert and known as the last drink of the meal. Alora. So with that we moved to end the food tour in another Tuscan way.

Gelato did originate in Florence during the 1500s Italian Renaissance . Gelato was officially developed by famous artist and architect Bernardo Buontalenti although some will claim alchemist Cosimo Ruggieri created the first-ever gelato (fior di latte) at the court of Catherine de’ Medici as part of a courtly cooking contest.

Nothing like a good story passed through centuries to change a little! 

We were now experts on finding good gelato, thanks to the tips we received on our street food tour of Rome , which Chiara reiterated on this tour. 

Earlier in the day, I had eaten the best gelato of my life, coincidentally also from Oltrarno. A month later I can still taste those melting bits of hazelnut chocolate inside the Stracciatella. (same with a gelato in Siena Tuscany )

Thank God for Florence. Chiara told us about 95% of the gelatos in Florence are good and the real deal. 

Gelateria Artigianale La Sorbettiera was founded in 2007. They continue to make authentic artisanal gelato paying attention to tradition but also emerging trends AND the dietary requirements of their customers. 

Chiara patiently told us all the flavors, as they were written in Italian, and helped us choose any combination of two flavors. 

At this gelateria you can taste what was the original recipe for gelato. It’s creamy and delicious, kind of like vanilla but without the vanilla. You’ll understand when you try it. 

What a sweet end to an exceptional food and wine tour in Florence. 

FAQs About Florence Food & Wine Tours

Below is what people ask us about food tours in Florence…

Well, ours joined us on our food and wine tour in Oltrarno! While all the stops involved wine, kids can have soda or juice. And each stop comes with food!

I think people from good food cultures like Italy and France , who are so seriously dedicated and passionate about good food, were raised embracing food culture like we experienced on this tour.

So that in itself is a positive reason for taking kids on a food tour. Especially since they are growing up in a fast food, eat-on-the-run kinda lifestyle, giving them the first-hand experience of slowing down to eat with a group of people and thinking about how food should be eaten and paired with what drinks is very valuable.

I do recommend this tour for older kids. There was another family with a 17-year-old, he was loving it.

It just depends on the ages and food-interest level of your kids. You may not want to spend that money a food and wine tour with kids. We joined the tour so we could write about it and share so our kids obviously came along!

As mentioned, I’m gluten free and could eat almost everything on the food tour. What I couldn’t was substituted for gluten free. If you have celiacs disease, you may not want to risk it. The tour is also adaptable for vegetarians and dairy free, but probably not for vegans. Note any requirements when booking. It was also one of the first things Chiara asked us at the start of the tour!

At the beautiful Piazza Santo Spirito by the statue of Cosimo Ridolfi in Oltrarno at 4:45pm Why not come earlier to soak up the atmosphere here? It’s also close to Pittie Plaza and the Boboli Gardens if you want to visit them before the tour. We did!

No, you don’t get to see the cellars or where the wine is produced on a food and wine tour of Tuscany, you just visit some of the best wineries, wine bars and restaurants where you can try the local wines.

In Conclusion

Because of this tour I was able to experience the deliciousness of Florentine steak, understand why I’ve not loved drinking Chianti before (it’s all about the missing food), and appreciate the sweet goodness of biscotti dipped in Vin Santo.

As always with Devour food tours, this was made even better by a friendly, informative local guide who shared much about Florentine history and culture.

I love the focus of these tours on local and tradition. It’s where you’ll find the best flavors and the best stories. 

As the sun was setting our small group dispersed, some going for a walk, some going home and others going to nearby rooftop bars for tangerine sky views over the lush landscapes. I don’t think any of us were planning to eat more food.

We walked along the river enjoying the setting home before dropping the girls off to our hotel (they were ready for Facetime with friends) so Craig and I went around the corner for one more glass of Tuscan red in yet another Enoteca.

I’m getting quite addicted to the Italian lifestyle: espressos, cappuccinos, aperitivos, and gelato to last the whole day! You may also want to see what other top things there are to do in Florence and this best of Florence walking tour which we enjoyed!

Click here to read more reviews and availability for the Oltrano food and wine tasting tour in Florence.