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16-Day Italy and Sicily Tour

tours to italy and sicily

The Italy and Sicily tour package is a magnificent all inclusive journey through seven Italian regions, including the island of Sicily plus Calabria, Campania, Lazio, Tuscany, Umbria and Veneto. 

The all-inclusive Italy and Sicily trip itinerary visits many of Italy’s UNESCO sightseeing highlights .  This escorted tour of Italy’s UNESCO Heritage sites travels Italy south to north, from Palermo to Venice.

tours to italy and sicily

Italy and Sicily Tours Sightseeing Highlights

  • PALERMO – Guided sightseeing, visit the Norman cathedral in Monreale
  • AGRIGENTO – Guided walking tour of the Valley of Temples
  • TAORMINA – Enjoy a walk along Corso Umberto.
  • POMPEII – Guided walking tour of the excavations
  • CAPRI – Funicular ride, guided sightseeing, visit the Gardens of Augustus
  • VENICE ISLAND – Private boat ride; guided walking tour, visit St. Mark’s Square and Basilica, Doges’ Palace, and the Bridge of Sighs; glass blower demonstration
  • FLORENCE – Guided walking tour, visit Michelangelo’s David and Signoria Square; dinner at a local restaurant
  • MONTERIGGIONI – Visit the medieval town and walk on its ramparts
  • ROME – Guided sightseeing, visit the Vatican Museums and Sistine Chapel, St. Peter’s Square and Basilica, and the Colosseum
  • CASTEL GANDOLFO – Guided visit of the Papal Palace and Barberini Gardens
  • CEFALÙ – Visit the seaside town; granita tasting

Italy and Sicily tour includes first-class accommodations .

To review the Italy and Sicily tour daily itinerary click here .

Accommodations

4-star italy and sicily vacation accommodations, palermo 2 nights – mercure centro, agrigento 1 night – dioscuri bay palace, taormina 2 nights – caesar palace giardini naxos, sorrento 2 nights – grand parco del sole, rome 2 nights – il cantico, assisi 1 night – cenacolo, la spezia 1 night – nh la spezia, florence 1 night – grand mediterraneo, venice 2 nights – le boulevard lido.

The Optionals and pricing listed here are a guideline only and subject to change.

Palermo Day 3

Sferracavallo with dinner – 60 euro.

Join us for a drive to the coast of Sicily, where we’ll arrive at the quaint fishing village of Sferracavallo. You’ll have the chance to sample Palermitano specialities, accompanied by wine and soft drinks.

A Visit To Cefalu – 36 Euro

Take a drive along the blue coastal highway to the quaint medieval village of Cefalu. You’ll have the chance to stroll from the long golden beaches into the winding Arab streets with your Local Specialist.

Taormina Day 5

Sicilian dinner and entertainment – 64 euro.

A fantastic Sicilian evening, you’ll enjoy a dinner of Southern Italian specialities with musical entertainment. Adult Price: EUR64.0*

Dinner in Castelmola – 75 Euro

Climb by minibus to the heights of Castelmola, above Taormina, to enjoy a tasty Sicilian Dinner with wine and musical entertainment in a characteristic restaurant with some of the best views of this magical part of the island.

Taormina Day 6

Mt etna, savoca and the godfather – 56 euro.

Discover rustic village life with your Local Specialist as we visit Savoca, the Sicilian setting for ‘The Godfather’. Enjoy the stunning views before a visit to Vitelli’s bar, featured in the film and famous for ‘granita di limone’. Later, you’ll journey up Mt Etna, one of the most intriguing volcanoes in the world.

Sorrento Day 8 – 42 Euro

Discover the isle of capri.

Experience Capri’s spectacular cliffs, famous turquoise waters and white grotto the best way – by boat! Enjoy a first­class view of this unique coastline. After the cruise, we ascend to Capri town, where there is time to take a stroll in this jet set haven and enjoy a local treat. In case of inclement weather, we’ll take you on a mini bus tour of the island to Anacapri, and visit Villa San Michele.

Neapolitan Dinner and Dance – 60 Euro

Join us for an evening of Neapolitan specialities at one of our favourite family ­run restaurants. While you’re wined and dined, enjoy a cultural experience performed by local artists who’ll take centre stage and demonstrate the famous Tarantella dance.

Sorrento Countryside and Farmhouse Meal – 50 Euro

Enjoy a beautiful drive into the Sorrentino countryside, where you’ll explore the gardens of a traditional local farm. During a tour of its lemon, orange and olive groves, your hosts will show you how mozzarella and other cheeses of the region are made. Then you’ll get to try cheeses, salamis and marinated vegetables, washed down with local wine and homemade bread.

Amalfi Coast Day 9

Amalfi coast and positano.

Come with us for a drive along the famous Amalfi Coast. You’ll have a chance to visit the exclusive artists’ paradise of Positano, which is magnificently positioned on the Mediterranean coast.

Rome Day 10

Piazzas and fountains of rome – 33 euro.

Discover the most charming areas in the city with a Local Specialist. Wander through the labyrinth of narrow streets and beautiful squares of Rome’s historic centre, leading to highlights such as the Trevi Fountain and the Pantheon, as well as hidden corners of the Eternal City.

Roman Evening with Dinner – 62 Euro

On this easy-going evening in Rome we visit one of our favourite restaurants, where you’ll enjoy a warm welcome and delicious dinner of local cuisine with drinks and music.

La Spezia Day 12

Sarzana dinner and drive – 63 euro.

Tonight we’ll go off the beaten track to the alluring medieval town of Sarzana , a hidden gem. We’ve chosen an elegant dinner venue where you’ll step into an atmosphere brimming with charm and unique character. It’s distinctive ambiance and culinary delights make it a firm favourite with the locals.

Florence Day 13

Dinner and wine in the tuscan hills – 65 euro.

This evening we’ll take a scenic drive to experience a fun and relaxed evening at a friendly, typical restaurant in the countryside. The chef will delight our senses with regional dishes, made with freshly-bought ingredients from the local farmers’ markets. Your delicious meal will be accompanied by excellent wines from the vineyards for which this area is so well known. In short, a Tuscan dream come true in an authentic setting.

Tuscan Dinner at Villa Machiavelli – 68 Euro

Through the Chianti hills, we’ll drive past vineyards to a delightful hamlet. Our destination is the ancient stone house of Machiavelli, where the great political theorist wrote his immortal work, ‘The Prince’. After a welcome drink and a visit of the villa and its wine-cellars, we’ll enjoy the best of Tuscan cuisine accompanied by great music and drinks, including of course, Chianti from the Villa’s own vines.

Venice Day 14 – 76 Euro

Gondolas and the grand canal.

Join us for a breathtaking cruise by private water taxi along Venice’s Grand Canal. You’ll admire the magnificent palazzi, as well as catching a glimpse of the Rialto Bridge and St. Mark’s Square. Later on, you’ll glide gracefully on a gondola along Venice’s dreamy, narrow waterways.

Venice Day 15 – 38 Euro

Venice’s secrets and st. mark’s basilica.

Explore the hidden maze of streets which make up this unique city as your Local Specialist gives you a fascinating insight into Venice’s past and present. You’ll visit the majestic Basilica of St Mark, where you’ll have a chance to view some of the prized trophies looted by the Venetians in their rise to power.

16-Day Italy and Sicily Tour Package Price

Check the box next to the Italy and Sicily escorted tour you would like to join.

  • Land with Air
  • Preferred Airport *
  • Apr 10, 2024 $4,995
  • Apr 17, 2024 Sold Out
  • Apr 24, 2024 Sold Out
  • May 01, 2024 $5,050
  • May 08, 2024 $5,050
  • May 15, 2024 Sold Out
  • May 22, 2024 $5,050
  • May 29, 2024 $5,050
  • Jun 05, 2024 $5,050
  • Jun 12, 2024 $5,050
  • Jun 19, 2024 $5,050
  • Jun 26, 2024 $5,025
  • Jul 10, 2024 $5,025
  • Jul 24, 2024 $4,995
  • Aug 07, 2024 $4,995
  • Aug 21, 2024 $5,025
  • Aug 28, 2024 $5,175
  • Sep 04, 2024 $5,175
  • Sep 11, 2024 Sold Out
  • Sep 18, 2024 $5,175
  • Sep 25, 2024 $5,175
  • Apr 09, 2025 $5,450
  • Apr 16, 2025 $5,450
  • Apr 23, 2025 $5,475
  • Apr 30, 2025 $5,495
  • May 07, 2025 $5,495
  • May 14, 2025 $5,495
  • May 21, 2025 $5,495
  • May 28, 2025 $5,495
  • Jun 04, 2025 $5,495
  • Jun 11, 2025 $5,495
  • Jun 18, 2025 $5,475
  • Jun 25, 2025 $5,475
  • Jul 02, 2025 $5,475
  • Jul 09, 2025 $5,475
  • Jul 23, 2025 $5,450
  • Aug 06, 2025 $5,450
  • Aug 20, 2025 $5,475
  • Aug 27, 2025 $5,525
  • Sep 03, 2025 $5,525
  • Sep 10, 2025 $5,525
  • Sep 17, 2025 $5,525
  • Travelers per room 1 2 3 4 5
  • Special Request
  • Name * First Last

Italy and Sicily Tours Itinerary

Tour Italy’s and Sicily’s UNESCO world heritage destinations including: Greek temples in Agrigento, the ancient Roman city Pompeii, Capri, Byzantine Mosaics in Monreale, Vatican City, Assisi, Cinque Terre, Florence, Rome, and Venice. 

Along your journey you will see two Italian volcanoes; Mt. Etna and Mt. Vesuvius. Tour Sicily’s highlights including Palermo and Taormina. Drive along the Amalfi Coast to the Bay of Naples resort town Sorrento. Cruise acriss the Bay of Naples by jet boat to the splendid island of Capri.

For the price of the Italy and Sicily tour with airfare included from your home city submit the form.

DAY 1 Depart the United States to fly to Sicily overnight

Board your flight and fly overnight to Palermo. The Italy and Sicily tour begins the evening of Day 2 in Palermo.

Day 2 Welcome to Palermo

The multicultural capital of Palermo launches your journey across Sicily and Italy. You’ll have some free time before meeting your Travel Director and fellow travellers for a Welcome Reception and orientation of the city’s attractions, so why not head straight out to explore its fascinating history on your own?

Day 3 Palermo and Monreale

Today begins in with a sightseeing tour of Palermo. Highlights include the beautiful opera house Teatro Massimo, and old ‘La Cala’ harbour.

Later, you’ll travel from Palermo to Monreale. Monreale is located on the slopes of Monte Caputo. It overlooks almond, olive and orange groves of La Conca d’Oro. In Monreale you’ll visit the 12th ­century Norman Cathedral, dedicated to the Assumption of the Virgin Mary. The cathedral is famous for its mosaics.

Meals: Breakfast

Optional Tours: Cefalu and Sferracavallo dinner .

Day 4 Travel across Sicily from Palermo to Agrigento

Today the Sicily and Italy tour continues first to Mondello. Here enjoy some time around this pretty resort town. Afterward, journey to Agrigento. There you’ll tour the impressive Greek Valley of the Temples, which date to the Magna Grecia era in the 6th century BC. This evening dinner is included at the hotel.

Meals: Breakfast and Dinner

Day 5 Travel from Agrigento to Taormina

Travel through the vineyards of the southern hills towards the seaside resort of Taormina, your home for the next two nights. Enjoy spectacular vistas and a taste of la dolce vita in this hillside town, with some free time on arrival.

Day 6 Taormina

Spend the day relaxing at your chic Sicilian resort. Dive into the warm Mediterranean waters, shop for exquisite hand-painted ceramics on Corso Umberto or indulge in a mulberry granita. Consider joining an Optional Experience to Savoca, the village made famous by ‘The Godfather’, or Europe’s most active volcano, Mount Etna. This evening, Connect With Locals over dinner at a Be My Guest experience hosted in the Jewish village of Castiglione di Sicilia as you roll up your sleeves to try your hand at making macaroni and end the day with a traditional Sicilian feast dining with the village locals.

Optional Tour: Mt Etna, Savoca And The Godfather .

Day 7 Travel from Sicily to Sorrento with Pompeii Tour

Today your Sicily and Italy tour continues by crossing the Strait of Messina by ferry boat to Italy’s mainland. Then, you’ll trael north through southern Italy’s Calabria region to Pompeii.

Pompeii is a UNESCO world heritage site. The ancient Roman city was covered by volcanic ash by the eruption of Mt. Vesuvius in 65 A.D. For centuries, the city was lost to the world – its rediscovery in the 18th century revealed a time capsule of well­-preserved ruins that provide insight into the Ancient Roman lifestyle. In Pompeii you’ll by joined by a local specialist for a walking tour of the ancient city.

Afterward, the tour continues to Sorrento where we’ll spend the next two nights.

Day 8 Isle of Capri

Today you’ll travel by jet boat across the Bay of Naples to the Isle of Capri. Upon arrival, you’ll enjoy a guided walking tour of Capri’s charming town. Then, you’ll have time to windowship the equisite made in Italy boutiques. or, spend your time sipping an apertif, indulging in a gelato, while people watching from a cafe in Capri’s center piazzetta. You may also join an optional tour to discover more of Capri .

Afterward, you’ll return to Sorrento. This evening is free to spend at leisure. Perhaps indulge in a local pizza and authentic limoncello in one of the town’s many cafés. Alternatively, there are two optional dinner excursions you may wish to join .

Optionals: Optional Tour: Discover Capri and two dinner options .

This morning wake up at leisure. Take a stroll around Sorrento.

You may also choose to join an optional tour down the Amalfi Coast to Positano .

Then, depart southern Italy and travel north to the ‘Eternal City’ Rome.

This evening, you will dive into the local Roman culture with an al fresco dinner against the spectacular backdrop of St. Peter’s in Rome. Marvel at Michelangelo’s magnificent 16th­ century frescoed ceiling in the Sistine Chapel and see the array of exquisite artefacts at the Museo Gregoriano Profano, founded in the Lateran Apostolic Palace at the behest of Gregory XVI Cappellari in 1844.

Optionals: Amalfi Coast drive to Positano .

Day 10 Rome – Vatican City and Ancient Roman Colosseum

Rome was once the capital of the world and is a city with an irresistible verve. Join your Local Specialist for a sightseeing tour to admire the city’s iconic and unexpected highlights.

First, head to the Vatican and see Michelangelo’s magnificent Pietà inside St. Peter’s Basilica.

Then, your next stop is Ancient Rome, where you’ll see Circus Maximus and visit the Colosseum where gladiators and slaves once fought to their deaths.

Spend the rest of the day exploring Rome at leisure. There is also an optional tour of Rome’s piazzas and fountains and an optional dinner with entertainment.

Optionals: Piazzas and Fountains of Rome and Dinner with Entertainment .

Day 11 Assisi

Today, you’ll depart Rome driving north to the Umbria region, often called Italy’s green heart. There, you’ll visit Assisi, the birthplace of St. Francis of Assisi. Assisi is a classic medieval hilltop town. Umbria is known for its medieval towns surrounded by fields of flowers.

In Assisi you be joined by a local specialist who will give you a tour of the Basilica of St. Francis. Inside, you’ll view its magnificent frescoes painted by Giotto. Tonight, you’ll stay in a fully renovated old Franciscan monastery.

Day 12 Pisa and La Spezia

Today you’ll travel north from Umbria into Tuscany. The first stop is Pisa. Upon arrival in Pisa you’ll visit the Field of Miracles. There you’ll see its most famous sight and iconic image, Leaning Tower of Pisa.

Afterward, you’ll take a short drive north to La Spezia. Located in Liguria on the coast, it is sometimes called ‘Pearl of the Tyrrhenian Sea’. This evening you have time at leisure to stroll around the town and enjoy the authentic Ligurian cuisine. Alternatively, join a n optional dinner excursion to Sarzana .

Optionals: Dinner excursion to Sarzana

Day 13 Cinque Terre and Florence

Today begins with an excursion to the Cinque Terre. The Cinque Terre is a series of five centuries-old seaside villages. The towns cling to rugged cliffs that plunge into the Ligurian Sea.

Afterward, continue to Florence, the birthplace of the Renaissance. Florence as a vibrant republic under the rule of the dynamic Medici family. Their love for art and antiquities created one of the world’s most cultural cities.

Upon arrival in Florence you have leisure time to see the sights on your own. Florence is also famous for its authentic Tuscan cuisine. Alternatively, you have the option to join one of two optional excursions to the Tuscan hills for dinner .

Optionals: Dinner and Wine in the Tuscan Hills or Tuscan Dinner at Villa Machiavelli

Day 14 Florence and travel to Venice

This morning you’ll enjoy a walking tour Florence’s historic center. Your local tour guide will take you to see Florence’s sightseeing highlights. The tour includes seeing the magnificent marble Duomo, Santa Croce Basilica, Ponte Vecchio and Piazza della Signoria. feature on your walking tour with a Local Specialist through Florence’s grand boulevards and narrow lanes.

Afterward head north from Florence to Venice, the ‘Queen of the Adriatic’. Upon arrival in Venice consider joining an optional excursion down the Grand Canal.

Optionals: Gondolas and Grand Canal Cruise

Day 15 Venice

Today’s Venice tour begins with an authentic glassblowing demonstration. The Venetian craftspeople are famous worldwide for their glassblowing art. You’ll watch how the master craftspeople shape the molten glass into the exquisite pieces that adorn homes all over the world.

Next, embark on an orientation cruise by private launch to the gateway of Venice, St. Mark’s Square, which Napoleon once called the ‘drawing room of Europe’. There you’ll see the Doge’s Palace, St. Mark’s Cathedral and the Bridge of Sighs, where prisoners would have one last look at their beloved city before facing imprisonment.

Afterward, you have the rest of the afternoon at leisure to explore more of Venice. Or, consider an optional experience, discovering the secrets of St Mark’s Basilica.

Tonight, you’ll join your fellow travelers for a Farewell Dinner and toast to shared memories that will linger long after the evening ends.

Day 16 Journey Home

Today your Sicily and Italy trip ends in Venice.

For more vacations to Italy and Sicily click  Sicily tours packages .

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Southern Italy & Sicily From $3,599 pp* Featuring Taormina, Matera and the Amalfi Coast

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Tour Activity Level

The activity level for this tour:

You’re a leisurely traveler. You typically take it easy and discover the energy of a new place by people-watching or soaking in the atmosphere at a local café. You can climb at least one flight of stairs, board a coach, and walk unassisted at a relaxed pace for up to 60 minutes without difficulty. You can easily handle altitudes up to 5,000 feet.

You like a balanced approach to travel. Walking two to three miles over the course of a day is no problem for you. You can partake in a two-hour leisurely walking tour, covering up to two miles (with included breaks). You can handle a variety of terrains, from cobblestone streets to moderate hills with relative ease and without assistance. You can climb two flights of stairs with ease. There may be 1 to 2 days on this tour when walking tours can cover 3 to 4 miles over uneven terrain. You can handle altitudes up to 6,000 feet.

You’re an on-the-go traveler. You don’t want to miss a thing, so walking and standing for longer periods of time (2-3 hours) isn’t a big deal. A moderately paced two-and-a-half-hour walking tour, covering several miles, hills, and uneven surfaces, is no problem for you. Walking four miles over the course of a day is very doable, as is climbing into and out of various modes of transportation (tuk-tuk, cable car, zodiac, etc.). You can climb three flights of stairs easily and handle altitudes between 6,000 and 9,000 feet. Expect some longer days balanced with free time to recharge or set out on your own adventure. This level is not a fit for travelers who require mobility assistance devices.

You’re ready to seize the day, whatever it may bring. You lead an active life at home (walking, biking, and half or full day hikes are things you may enjoy) and 10,000 steps a day is normal for you. You can handle longer walking tours (more than 3 hours covering 3+ miles at a steady clip) and activities that involve traversing uneven terrain, steep slopes, standing for periods of time, and varying altitudes and temperatures. You don’t mind being on the go with some early starts, late-nights, and full days. You can handle altitudes of 9,000 feet or higher with little to no issue. This level is not appropriate for travelers who use wheelchairs, walkers, and other mobility assistance devices.

Southern Italy & Sicily

Southern Italy & Sicily featuring Taormina, Matera and the Amalfi Coast

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Southern Italy & Sicily

With apulia & the amalfi coast.

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Delight in a special exploration of Italy’s southern climes, from striking Sicily and the breathtaking Amalfi Coast to unheralded Apulia, the alluring “boot heel” where a vivid history, unique architecture, and bountiful plains join the sun and sea in creating a prized (and crowd-free) region.  Add Italian hospitality, outstanding cuisine, and notable lodgings for la dolce vita , small-group style.

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Tour Details

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From $5,074

Small Group Highlights

  • Sicily’s intriguing cultural and historic heritage
  • “Valley of the Temples,” Agrigento
  • Mt. Etna excursion
  • Lunch at a working Sicilian farmhouse
  • Two Apulia UNESCO sites: cave dwellings of Matera and Alberobello’s medieval white-washed buildings
  • Neapolitan cooking demonstration and dinner
  • Lecce, the “Florence of the South”
  • Fascinating, uncrowded Apulia region
  • Stunning Amalfi Coast
  • Tour of ancient ruins at Pompeii (UNESCO site)
  • Day trip to Isle of Capri
  • Unique, well-located, small-group style hotels
  • Pleasing mix of touring and time at leisure

tours to italy and sicily

Day-by-Day Itinerary

Please note: We use a variety of distinctive hotels in Lecce, as listed below. For specific accommodations per departure date, click on the Reservation Request button in the Dates & Prices section below or call for more information.

tours to italy and sicily

The Eurostars Monte Tauro enjoys an incredible location in Taormina. The hotel cascades down a hillside at the edge of the town’s center, offering an easy walk to many shops and restaurants and also an unspoiled view across the sparkling Ionian Sea.  Amenities of this 98-room hotel include a restaurant and bar overlooking the water; outdoor swimming pool with water views, hydro-massage jets, and a lounge area; spa services; laundry and dry-cleaning services (for a fee); and complimentary Wi-Fi internet access.  Each air-conditioned guest room has a private deck overlooking the water and features private bath with hair dryer, minibar, in-room safe, TV, and phone.

tours to italy and sicily

The 32-room Locanda di San Martino offers guests the rare opportunity to stay in cave dwellings created thousands of years ago – but updated with contemporary comforts and modern amenities.  Passageways cut into the rock, external staircases, and elevators connect all four levels of the hotel.  The focus of our stay is the unique experience the hotel can offer in an area famous for this type of dwelling.  While your room is clean and comfortable, it will not be as luxurious as hotels on other parts of your tour.  Fresh local food is brought to the hotel for each meal because the hotel does not have a kitchen.  Locanda di San Martino is in the heart of Matera’s “ Sassi ” Historical District, very close to the city center.  The hotel has a bar and breakfast room; air-conditioned guest rooms have private bath with hair dryer, complimentary Wi-Fi internet access, and TV.  Please note that because of the historical nature of the hotel, room sizes and views vary, and you must pay attention to the stairs around the hotel and within your room.

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The 18-room Chiostro dei Domenicani is set within a 15th-century Dominican convent. The cultural and historical Italian charm remains today, with original Lecce stone structures, Doric-style columns, and detailed frescoes throughout. Along with spacious common areas and large, comfortable rooms, the hotel offers a seasonal outdoor swimming pool, garden, terrace, restaurant, wine bar, and complimentary Wi-Fi internet access. Air-conditioned guest rooms preserve the characteristic structure of the former convent with tasteful yet simple décor, and include private bath with hair dryer, minibar, tea- and coffee-making facilities, in-room safe, TV, and phone.

tours to italy and sicily

This 19 th -century mansion was once a private residence and today operates as a 41-room hotel that blends historical charm with modern comforts. Located inside the historic city center, Risorgimento Resort is just steps away from some of Lecce’s most iconic sites, such as the Cathedral of Maria Santissima Assunta and Sant’Oronzo, Piazza sant’Oronzo, and the Roman Amphitheatre. Hotel amenities include a restaurant, lounge bar, rooftop garden terrace with views of the bell tower of the Duomo, spa with massage services (for a fee), laundry service (for a fee), and complimentary Wi-Fi internet access. Air-conditioned guest rooms have private bath with hair dryer, minibar, in-room safe, TV, and phone.

tours to italy and sicily

This historic hotel sits in the heart of Sorrento on Piazza Tasso, the main square, close to shops and restaurants.  Amenities of the intimate 46-room Hotel Antiche Mura include an outdoor swimming pool, solarium, lovely gardens with a citrus grove (which supplies all of the oranges and lemons used by the hotel), lobby bar, outdoor snack bar, breakfast room, complimentary Wi-Fi internet access, and laundry and dry-cleaning services (for a fee).  Art nouveau-style guest rooms have private bath with hair dryer, in-room safe, minibar, TV, and phone.  Air conditioning is available from May through October; heat from November through April.

Tour Price Includes

  • Round-trip air transportation from listed cities
  • 13 nights’ accommodations in Superior First Class and First Class hotels
  • 26 meals: 13 breakfasts, 5 lunches, 8 dinners
  • Extensive sightseeing as described, including all entrance fees
  • Services of an Odysseys Unlimited Tour Director
  • Private motorcoach transportation throughout your trip
  • Luggage handling for one bag per person
  • Gratuities for local guides, dining room servers, airport and hotel porters, and all drivers
  • $100 frequent traveler credit towards your next Odysseys Unlimited tour ($200 after 3 tours; $300 after 10 tours)

tours to italy and sicily

Average Daily High by Month (°F )

Average temperature (°f ), dates & prices.

Airline upgrades (subject to availability; pricing subject to change) on round-trip Trans-Atlantic flight: Business Class – $3,795 per person in 2024; $3,995 per person in 2025. Premium Economy – $1,595 per person in 2024; $1,795 per person in 2025

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Post-Tour Extension

tours to italy and sicily

Rome – On Your Own

Explore the Eternal City at your leisure.

Post-Tour Extension Price Includes

  • Private transportation Sorrento/Rome
  • 3 nights’ accommodations at Monti Palace Hotel (Superior First Class)
  • 3 meals: 3 breakfasts
  • Transfer to airport

Pricing: $795 in 2024; $695 in 2025. Single Supplement: $295 in 2024; $245 in 2025

Accommodations

tours to italy and sicily

Sitting just a 10-minute walk from Rome’s famed Colosseum, the Monti Palace Hotel occupies a 19 th -century building in the heart of the Eternal City.  Amenities of this stylish and contemporary hotel include a rooftop bar with terrace overlooking the city, library bar and lounge, 24-hour fitness center, laundry services (for a fee), and complimentary Wi-Fi internet access.  Air-conditioned guest rooms have private bath with hair dryer, in-room safe, minibar, tea- and coffee-making facilities, TV, and phone.

tours to italy and sicily

Tour Directors

tours to italy and sicily

“Her knowledge was amazing, she was fun to be with, and built a real community among the travelers. You knew that each of us was the most important person in her life for those 14 days.”

Thomas & Mary Heyman Montclair, NJ

tours to italy and sicily

“Anna was THE BEST! Unfailingly patient, friendly, helpful, knowledgeable, warm, and a joy to be around. I cannot list enough positive descriptions for her. She is a gem!”

Henry & Susan Fradkin Dearborn, MI

tours to italy and sicily

“Daniela is an asset to your company. Her knowledge and love for her country are remarkable. She is simply 'Magnifico' and 'so Italien.'”

Cary Jane Miller Corona del Mar, CA

tours to italy and sicily

“Osh [was amazing]…He has a wonderful personality, and helped [the group] bond as a unit. We loved him also.”

Bonnie & Douglas Herr Williamstown, MA

tours to italy and sicily

"Arianna went way above her duties as a tour director. She was very knowledgeable, friendly, patient, [and] helpful."

Kathryn Barton Rochester, NY

tours to italy and sicily

"Ingrid’s warmth, courtesy, professionalism, and genuine concern made her an absolute pleasure to travel with. With infinite patience and gentle humor, she shared her knowledge and enthusiasm and made our travel stress-free."

Michael & Colleen Thompson The Woodlands, TX

tours to italy and sicily

“Katia was hands down the best tour director we have ever had! She was sweet, funny, intelligent, efficient, knowledgeable, and really went way beyond what she had to do…we loved her!”

Jim & Sue Sanders Plainwell, MI

tours to italy and sicily

“You are fortunate to have Sara on your staff. She is the greatest! Her energy, dedication, and professionalism are beyond anything we have seen.”

William Garro Boonton, NJ

tours to italy and sicily

“Best tour director ever! She went way above and beyond expectation.”

John & Jane Pratt Newbury, NH

tours to italy and sicily

Odysseys Unlimited Tour Director

tours to italy and sicily

“She was wonderful!”

Layton & Marsha Carr

tours to italy and sicily

“He did his homework and personally knew the other staff people on the ground.”

Cecilia & Francis Kelly Hartford, NC

tours to italy and sicily

"An excellent combination of steel and velvet: firm grasp on all logistics…combined with a caring attitude for each member of the group."

Stephen Rose & Patricia Midgette Virginia Beach, VA

tours to italy and sicily

“Andrea is a gem (diamond). His knowledge, enthusiasm, caring, and competence cannot be overstated. He’s an exceptional leader.”

Nancy Munno Montpelier, VT

tours to italy and sicily

“Maurizio is a treasure. What a fabulous tour director he is. His knowledge, stories, and wonderful personality made this tour even better. I could feel his love of Italy, his love for people and his love for his job. He is doing exactly what he is meant to do.”

Carol Kut Chepachet, RI

tours to italy and sicily

"On this, our 11 th Odysseys tour, we encountered a tour director who exceeded the high standards set elsewhere. Giulia was pure joy: warm, welcoming, with a great sense of humor."

Roger & Donna Authers Charlottesville, VA

tours to italy and sicily

“Marina was outstanding. She was alert to individual needs and extremely helpful throughout the trip.”

John & Arleen Cooper Arvada, CO

tours to italy and sicily

"Elizabeth was beyond exceptional in all areas. Her attention to detail and individual needs was superb; her knowledge…of the areas outstanding; and her management of the group truly admirable."

Gale Wood & David Dewsnap Havertown, PA

tours to italy and sicily

“We could not have had a better tour director. Her information about olives, local fare, gelato, and the region was truly an asset to the trip… She is a real treasure!”

Kay & Sherman English Seattle, WA

tours to italy and sicily

“[Gaetano] was not only knowledgeable and efficient, but had a great personality and was very funny. The stories he told about his personal experiences greatly enhanced the overall tour. He was one of [the] best we have had.”

Steven & Royce Menkus Sherman Oaks, CA

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Physical Activity Level

  • Walk 2-4 miles per day, often on uneven terrain or cobblestones
  • Occasional long walks from motorcoach drop-off to sights and hotels
  • Uneven natural terrain at Mt. Etna and at Agrigento and Pompeii archaeological sites
  • Steep grades while walking in Taormina
  • Many stairs of varying height throughout the tour
  • Embarkation/disembarkation from multiple boats
  • Several long days of travel via motorcoach
  • Locanda di San Martino hotel (Matera) does not have an elevator that has access to each floor

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Country Roads of Southern Italy & Sicily

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Country Roads of Southern Italy and Sicily Guided Tour

2 countries

Country Roads

Learn the Secrets to Living 'la Dolce Vita' During This 2-Week Guided Tour of Italy

Indulge in Italy’s finest food and views during this 2-week guided tour. When in Rome, you will toss a coin into the Trevi Fountain during a walking tour with a Local Expert. At the Vatican Museums, get a behind-the-scenes look at the Bramante Staircase, a winding masterpiece normally closed to the public. In Sorrento, settle into a luxurious resort and take in the views of Mount Vesuvius, which buried Pompeii in a sea of lava in 79 A.D. A restaurant’s founder will share why he uses only organic ingredients that he grows himself — and you will indulge in those freshly picked vegetables during a farm-to-table dinner featuring fresh orecchiette pasta. In Palermo, a historian will take you through the old city, showing you its cathedral and the Palatine Chapel in the Palace of the Normans, where glittering 12th century mosaics will surely take your breath away.

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Start Rome, Italy. End Palermo, Italy.

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Our specialists can design a bespoke itinerary for you. You'll experience the Insight Difference with a passionate Travel Director, all tailored to your group's personal interests. 

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Travel knowing our 4-point climate action plan will ensure net-zero greenhouse gas emissions by 2050.

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Your your directly supports local communities by visiting family-run businesses, UNSECO sites and places of cultural significance.

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Italy Tour Packages 2024, 2025

Are you ready to explore the history and modern day marvels of Italy from a Protestant perspective? Join other Christian evangelicals in seeing sites of significant church history and places that inspired Paul’s letter to the Romans. See why Paul’s missionary journeys led him to Italy and how this has impacted the world. Enjoy excellent preserved archaeological ruins such as the Coliseum, stunning works of art at the Vatican in Rome and Academia Gallery in Florence, and architectural wonders such as the canals in Venice. Several tours combine Italy with Greece to hit several different cities that Paul visited.

Below is a list of various tour packages departing year-round.

Reserve your tour at least 6 months in advance for an early booking discount, groups and parties of 6 or more click here for special rates, scheduled 2024 & 2025 italy tours/cruises, italy tours: frequently asked questions.

What is the best month for an Italy tour?

You can book one of our Italy tours during any time of the year, but different seasons offer different benefits. Visiting during the summer means the weather will be sunny and warm, while winter visits can mean snow — especially in mountainous regions. Since the weather is great during the summer, it’s also the busiest season in terms of visitors. We offer Italy tour packages throughout the year, so you can find a tour that works for your schedule and includes all the destinations you want to see.

How many days do you need for an Italy tour?

The length of our Italy trip packages varies quite a bit. Our shortest Italy tours are 8 days long, while our longest tour lasts 23 days and gives you a chance to visit several countries. Our shorter tours allow you to choose where you want to go and what you want to see, or you can choose our Best of Italy tour to see some of the most popular spots. Our longest tour packages combine our Greece tours , Italy tours and others to give you a more well-rounded experience.

What is the dress code in Italy?

Italy doesn’t have an especially strict dress code, so you don’t have to worry about wearing traditional garments when you visit. That being said, Italy is a fashion-conscious country where many people dress well, so you’ll feel right at home if you like to dress up a bit. Like our Greece and Turkey tours , our tours of Italy may include visits to religious sites that have their own dress code. These dress codes usually involve dressing modestly, so make sure you pack more than shorts and tank tops.

Is there a lot of walking involved on an Italy Tour?

The amount of walking depends on which of our Sicily & Italy tours you choose. However, it’s always smart to pack a comfortable pair of shoes when you’re visiting another country. Walking shoes that provide support and cushioning are ideal because they help you avoid foot pain. If you’re concerned about how much you’ll need to walk during your tour, you can contact us before booking but we generally suggest that each day will involve several miles of walking on average.

What passport & visa information do I need for your Italy tours?

If you’re a U.S. citizen, you can visit Italy for up to 90 days for tourism or business purposes without worrying about getting a visa. However, you will need to have a valid passport to visit Italy. Since obtaining a passport can take several weeks — even with an expedited application — you should make sure you have you have applied for your passport at least 4 months before your trip.

What common languages will be spoken during the Italy tours?

Italian is the most commonly spoken language in Italy, with about 93% of the population being native speakers. The good news is that English is the second most common language in the country, so it’s usually easy to find someone you can communicate with at a shop or restaurant. We also have English-speaking tour guides who will accompany you on any of our Italy tours.

What currency can I use on an Italy tour?

The euro is the most commonly used currency in Italy, so you’ll need to exchange your money for euros before visiting. Whether you’re booking a trip to Sicily or Italy or one of our Britain and Scotland tours , we recommend visiting a currency exchange before your trip. If you have extra money left over, you can always exchange it for USD or keep it as a souvenir.

Do I need to bring a converter for the Italy tour?

Italy uses three different types of plugs: Type C, F and L. If you want to make sure you can plug your devices in wherever you go, make sure you have these three adapters. You can also find all-in-one adapters that work in any country, so you can use them for our Turkey or Germany tours after you’re done visiting Italy.

What is the time zone for your Italy tours?

The time zone used in Italy is called Central European Time (CET), which means Italy is 9 hours ahead of the western United States and 6 hours ahead of the eastern United States. You may experience jet lag when you visit Italy for the first time.

What climate should I expect during my Italy tour?

Unlike our Iceland tours which offer a more consistent climate year round, Sicily & Italy tours are great because you can experience vastly different types of weather during different seasons. The climate during the summer is warm and sunny without being overwhelming, while many parts of Italy get a significant amount of snow each winter.

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Rome and Sicily Itineraries & Tours

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Celebrate two distinctive regions of Italy that each host an iconic culture, cuisine, and history. Rome and Sicily stand as testaments to ancient and modern marvels, and their endless enchanting qualities are waiting for your discovery. Explore the variety of Italy with your Rome and Sicily itinerary from Zicasso.

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Vineyards in Sicily, Italy

8  Day Custom Tour

Dynamic pricing from  $2,859

Combine traditional flavor with ancient history, and Baroque charm with rich landscapes during your custom-tailored wine tour of Sicily for seniors. The indelible marks of ancient settlers gave rise to stunning culinary delights while elegant towns capture the grandeur of former kingdoms. Your immersive tour will highlight the treasured sunsets in Noto and luxurious coastline at Marzamemi, as well as the bountiful vineyards that spread across the foothills of Mount Etna. You will capture the spirit of the local markets that reveal customary recipes and explore the isolated islands that overflow with hidden splendors to shape your perfect blend of the past and present of Sicily.

View of the city of Taormina and Mount Etna, Sicily

7  Day Custom Tour

Dynamic pricing from  $2,501

Romance will be in the air during this 7-day couple’s vacation to the stunning island of Sicily. Explore the best parts of the island as you uncover the beauty, history, and delicious food of Italy’s largest island. Dinners for two and exclusive experiences will be yours to enjoy as you indulge in all Sicily has to offer during this remarkable and unforgettable vacation.

Amalfi Coast, Gulf of Solerno

14  Day Custom Tour

Dynamic pricing from  $5,007

While in Italy, you can sink into luxury and let the ancient world spring to life around you. Mosaics from Pompeii remain vibrant with lifelike images and exciting colors as Greek ruins rise out of the mountaintops and plains of Sicily. The Mediterranean Sea brushes at the beaches and boulders that line the Amalfi Coast. Hidden waterfalls feed abandoned paper mills and a treasure trove of artwork decorates the galleries of the Vatican Museums. Your custom tailored tour combines the wonders of the landscape and the splendors of history for a special expression of Southern Italy’s unforgettable and distinguished culture.

Young girl enjoying a gelato in Rome, Italy

10  Day Custom Tour

Dynamic pricing from  $3,575

Become gladiators, search for priceless paintings, and indulge in unforgettable adventures with a custom tailored family-friendly Italy itinerary. Relish a chance to blend fun and education with culture that the kids can touch. Knead handmade pasta dough under the guidance of a private chef and then wander through hidden corridors and along the labyrinthine Hypogeum in the Colosseum. Explore extinct volcanic craters and learn the art of making fresh gelato in a medieval town. Your private family Italy tour itinerary will offer flavorful delights, ancient marvels, and secret catacombs to create memories that will last a lifetime.

The coast of Sorrento in Italy

12  Day Custom Tour

Dynamic pricing from  $9,199

The wonders of Rome, the coastal Campania region, and Sicily come alive on this 11-day tour of Italy's southern half. From the Italian capital to the bustling port city of Palermo, enjoy a balanced itinerary that combines guided excursions, food tours, and ample free time to bask in all that is best of the regions you visit.

Couple at a luxury resort pool surrounded by vineyards in Selinunte, Sicily

9  Day Custom Tour

Dynamic pricing from  $3,217

Capture the romance of Italy during your custom-tailored Sicily wine tour for couples. Revel in the perfect mixture of seductive history and enchanting flavors with private tours that offer exclusive access to boutique vineyards from Palermo to Marsala. The art and artistry of tradition bring a deep well of heritage that spans the millennia and shapes the captivating ambiance in which you will find Byzantine mosaics, ancient Greek architecture, delicate olive oil, and complex wines. Relax in the beauty of seaside towns, indulge in the splendor of golden architecture, and embrace the immersive panoramas seen during your luxurious wine tour of Sicily.

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Sicily Small Group Tours

Uncover new and exciting adventures in Sicily by taking part in our small group tours. Go sightseeing at your own pace surrounded by travellers like you. Provided by top tour operators & travel companies, our small group tours in Sicily will offer you the perfect balance between spending time on your own and group activities. View all small group tours .

61 Sicily small group tours with 431 reviews

Small Group Tour of Sicily: Highlights (Maximum 8 Guests) Tour

  • In-depth Cultural
  • Food & Culinary
  • Hiking & Trekking

Small Group Tour of Sicily: Highlights (Maximum 8 Guests)

Great communication from beginning to end! We were provided the tour exactly how it was offered with knowledgeable guides and drivers. The hotels and meals were outstanding!
  • 10% deposit on some dates Some departure dates offer you the chance to book this tour with a lower deposit.

Small Group Sicily Food & Wine Tour (Maximum 8 Guests) Tour

Small Group Sicily Food & Wine Tour (Maximum 8 Guests)

Trip was excellent from beginning to end. Excellent itinerary and accommodations. Guides were very friendly and knowledgeable. Massimo and Graziana are extraordinary with their communication and availability. A pleasure to deal with persons like these! Highly recommend!

Sicilian Landscapes: Catania-Catania (8 days/7 nights) Tour

  • Coach / Bus

Sicilian Landscapes: Catania-Catania (8 days/7 nights)

It was one of the best tours I have ever been on. It was jam packed with excursions every day and our tour guide Angelo was very knowledgeable, friendly and couldn’t do enough for us.
  • €50 deposit on some dates Some departure dates offer you the chance to book this tour with a lower deposit.

Best of Sicily - 8 Days (Small Group Tour) Tour

Best of Sicily - 8 Days (Small Group Tour)

The tour was truly a taste to Sicily. The tour guides were knowledgeable and thorough from Taormina to Palermo. The hotels and the choice of meals were very good especially the wine tasting at Etna having the most inventive cuisine.

New Tour The Best of Sicily & Malta - 11 Days Tour

New Tour The Best of Sicily & Malta - 11 Days

Sicily tour was very good. Angelo-the tour guide is avery good guide and a very good person. I just recommend background i for to be brief or provide them during the bus drive so that we can have plenty of free time in each area. Malta trip is okay-except that the itinerary is not followed by the guide. In addition-it's too much detail in one location that shortens the time to see more and prevents having free time.

Sicily, From Palermo to Catania Private Tour Tour

Sicily, From Palermo to Catania Private Tour

Reasonable accomodation good drivers no guide support you are on your own . Though the tour is advertised as private guided tour Only accomodation and private car booked no guide support the driver is said to be driver and guide . He says his job is driving only . Please stop advertising as private guided tour it is not .

Charming Sicily Food & Wine Small Group Tour - 8 days Tour

  • Wine tasting

Charming Sicily Food & Wine Small Group Tour - 8 days

Overall our tour was wonderful. We had a great time. Denise, especially was a very good guide, very knowledgable and personable. The cooking class and our Palermo Street Food tour was, probably my favorites. A few areas that could have been improved upon: - A little more communication prior to the tour would have been reassuring. In this day of fraud it is a little unnerving to send all that money into the internet and not get much of a response. - The final communication, our itinerary, was a definite problem. We were told by Tour Radar that we would receive it 10-14 days before we left. The tour operator (ClickTours/Mossimo) told us we would receive it 8 days before we left. I finally called Tour Radar 6 days before we left

Sicilian Pearls: Palermo-Catania (5 days/4 nights) Tour

Sicilian Pearls: Palermo-Catania (5 days/4 nights)

Included destinations were a "must-see" for a comprehensive tour of Sicily. I feel it should have been more spread out by 1 or 2 days so as not to feel so rushed; some days with too many hours on the bus and too early a start in the day. Placido was a very good guide. His flluency in English was very good albeit sometimes difficult to understand ( pronunciation.) Also, perhaps too much detail in historical context for the casual (non-academic) tourist. The included dinner in Pallermo, by general consensus of the tour members, was not good. Many dinners left unfinished on the table...warm pasta with fish. The hotel in Agrigento was marvelous!

Charming Sicily - 2024 Tour

Charming Sicily - 2024

Highlights of Calabria & Sicily (including Aeolian Islands) Tour

Highlights of Calabria & Sicily (including Aeolian Islands)

Sicily Food Adventure Tour

Sicily Food Adventure

Well planned tour. Tour leader Rosario was the best. He made the tour very, very special. So very professional, caring and expert. Highly recommend this tour.

The Best Highlights 7 Day Sicily Tour 2024 - Max 7 people Tour

The Best Highlights 7 Day Sicily Tour 2024 - Max 7 people

The Best way to see Sicily is through the eyes of a true Sicilian and that is exactly what we got with HandiSicily. We got to experience the passion and love Paolo has for his home country. The rest of the tour was 5 stars all the way. The locations, History, the food and wine exceeded all expectations. Overall an unforgettable experience. Thank you HandiSicily.

Rome to Sicily (20 destinations) Tour

Rome to Sicily (20 destinations)

Premium Sicily Tour

Premium Sicily

Women\'s Adventures Tour

Women's Adventures

Reviews of small group tours to sicily.

The tour was wonderful. We had great guides, delicious food, and enjoyed the beauty of Sicily.
I can’t say enough good things about our experience in Sicily thanks to Mossimo and his team. Excellent, informative tour guides…Denise, Carlos, Antonio and Sem. The cooking class may have been the highlight, but all of the activities were fun and the pace of the tour, planned activities/free time mix was perfect. Will definitely recommend!
Generally speaking the tour was good. Hotels, foods, itinerary, tour guide were all satisfied. the only thing made me unhappy even panic was no taxi driver waiting at Catania airport arrivals although I booked in advance. It's about 22:30, I phoned the emergency number, the lady replied in Italian, we could not understand each other, so she shouted and put down phone. Then I asked an Italian for help. He made a call and got one can speak English. I was told the driver was in a airport bar, then I found the bar was closed and the driver was at outside of the bar, eventually he took me to the hotel, that was very late. The people responds emergency number cannot speak English?! The taxi driver 'with a sign with your surname on it' was not waiting at the arrivals as I was told. What was a shock for a person arrived in Catania first time at late evening and start a tour next morning?!
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Colours of Sicily Guided Tour

9 Day Sicily Sightseeing Tour

9 days, 1 country and 10 cities

Accommodation

8 Breakfasts, 4 Dinners

View day-by-day trip itinerary

Sicily’s vibrant palette of colors comes alive on this trip. Sip local wine on the slopes of Mount Etna, wander the chic streets of Taormina and meet the locals in colorful fishing villages. Top it all off with a sweet treat – all the Modican chocolate you can lay your hands on.

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Day by day itinerary

9 days itinerary trip from Palermo to Catania visiting 1 country and 10 cities

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About this trip

Sightseeing highlights.

Explore Palermo, Monreale, Valley of the Temples, Ragusa, Syracuse and Taormina with a Local Specialist

Discover Modica and Catania

Visit Monreale Norman Cathedral, Erice, Infersa Mill in Marsala, Valley of the Temples, the Syracuse Archaeological Museum, Ortygia and the Greek Theater in Taormina

View Mount Etna (optional)

Travel highlights

Specific transfer information can be found here:

Airport Transfers

An expert Travel Director and professional Driver

Cherry-picked hotels, all tried and trusted

All porterage and restaurant gratuities

All hotel tips, charges and local taxes

Breakfast daily and up to half of your evening meals

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AFAR

The 7 Best Italy Cruises to Book Now

Posted: October 8, 2023 | Last updated: October 8, 2023

<p>Visiting Sicily is a must on any Italy sailing.</p><p>Courtesy of Flo/Unsplash</p><p>When it comes to <a class="Link" href="https://www.afar.com/travel-guides/italy/guide">Italy</a> cruises, your best bet is to go with a small-ship sailing. Big ships tend to do the tried and true—<a class="Link" href="https://www.afar.com/travel-guides/italy/rome/guide">Rome</a>, <a class="Link" href="https://www.afar.com/travel-guides/italy/venice/guide">Venice</a>, <a class="Link" href="https://www.afar.com/travel-guides/italy/florence/guide">Florence</a>, Naples—not that there’s anything wrong with seeing the Colosseum, St. Mark’s Square, Michelangelo’s <i>David</i>, and the ruins of <a class="Link" href="https://www.afar.com/magazine/pompeiis-museum-reopens-to-display-ancient-excavations">Pompeii</a>. But on the best cruises around Italy, there’s opportunity to go deeper and at a slower pace.</p><p>You’ll often still be able to check off major marquee attractions, while at the same time admiring the pastel-colored villages and hairpin roadways along the Amalfi Coast, the unspoiled landscapes of Puglia, the drama of Sicily, or the dreamy Ligurian coast. In addition to visiting off-the-beaten-path places, small ships tend to linger in ports, with the best itineraries including late evening or overnight stays. That way, there’s time to sample the dining scene—key for cruisers like me who like to try the local pasta dish in every town.</p>

Visiting Sicily is a must on any Italy sailing.

Courtesy of Flo/Unsplash

When it comes to Italy cruises, your best bet is to go with a small-ship sailing. Big ships tend to do the tried and true— Rome , Venice , Florence , Naples—not that there’s anything wrong with seeing the Colosseum, St. Mark’s Square, Michelangelo’s David , and the ruins of Pompeii . But on the best cruises around Italy, there’s opportunity to go deeper and at a slower pace.

You’ll often still be able to check off major marquee attractions, while at the same time admiring the pastel-colored villages and hairpin roadways along the Amalfi Coast, the unspoiled landscapes of Puglia, the drama of Sicily, or the dreamy Ligurian coast. In addition to visiting off-the-beaten-path places, small ships tend to linger in ports, with the best itineraries including late evening or overnight stays. That way, there’s time to sample the dining scene—key for cruisers like me who like to try the local pasta dish in every town.

<p>When it comes to <a class="Link" href="https://www.afar.com/travel-guides/italy/guide">Italy</a> cruises, your best bet is to go with a small-ship sailing. Big ships tend to do the tried and true—<a class="Link" href="https://www.afar.com/travel-guides/italy/rome/guide">Rome</a>, <a class="Link" href="https://www.afar.com/travel-guides/italy/venice/guide">Venice</a>, <a class="Link" href="https://www.afar.com/travel-guides/italy/florence/guide">Florence</a>, Naples—not that there’s anything wrong with seeing the Colosseum, St. Mark’s Square, Michelangelo’s <i>David</i>, and the ruins of <a class="Link" href="https://www.afar.com/magazine/pompeiis-museum-reopens-to-display-ancient-excavations">Pompeii</a>. But on the best cruises around Italy, there’s opportunity to go deeper and at a slower pace.</p> <p>You’ll often still be able to check off major marquee attractions, while at the same time admiring the pastel-colored villages and hairpin roadways along the Amalfi Coast, the unspoiled landscapes of Puglia, the drama of Sicily, or the dreamy Ligurian coast. In addition to visiting off-the-beaten-path places, small ships tend to linger in ports, with the best itineraries including late evening or overnight stays. That way, there’s time to sample the dining scene—key for cruisers like me who like to try the local pasta dish in every town.</p> <h2>The best time for an Italy cruise</h2> <p>The main season for Italy cruises is April to October, coinciding with weather that increases the allure of beaches and outdoor attractions, even if visiting ancient ruins in the heat of summer may require some fortitude.</p> <h2>Where Italy cruises sail</h2>

The best time for an Italy cruise

The main season for Italy cruises is April to October, coinciding with weather that increases the allure of beaches and outdoor attractions, even if visiting ancient ruins in the heat of summer may require some fortitude.

Where Italy cruises sail

<h3>Amalfi Coast</h3> <p>Along the famed <a class="Link" href="https://www.afar.com/travel-guides/italy/amalfi-coast/guide">Amalfi Coast</a>, ships visit Sorrento, overlooking the bay of Naples, and colorful Amalfi, dramatically backed by steep cliffs. Some itineraries also including the strikingly beautiful Positano. Smaller yacht vessels may sail directly to the fancy island of Capri (otherwise there will be a shore excursion, as with the larger ships). Among other shore choices in this region is a visit to ancient Pompeii.</p> <p><b>Sicily</b></p> <p>Italy cruise itineraries often land at several ports on Sicily, and some itineraries circumnavigate the island. Each port has its own allure, including the city scene in Palermo; Syracuse, which showcases ancient attractions from when it was a prominent Greek city; Taormina, with its impressive hilltop location and Greek theater; and Lipari, which has a charming, tiny island ambience. In addition to striking landscapes, attractions include Roman and Greek ancient historic sights and views of Mount Etna, plus filming locations featured in <i>The Godfather</i> movies and in Season 2 of the HBO series <a class="Link" href="https://www.afar.com/magazine/white-lotus-season-2-filming-locations-you-can-visit"><i>The White Lotus</i></a>. If while cruising Sicily your ship ventures to Stromboli, with its famous volcano, it will be from a safe distance—and if you’re lucky, in the dark when you can witness the lava flowing.</p> <h3>Puglia</h3> <p>Increasingly popular on the cruise map are destinations in <a class="Link" href="https://www.afar.com/magazine/the-best-way-to-discover-italys-unspoiled-province">Puglia</a>, a region of olive groves and national parks. Small ships call in the city of Lecce and town of Gallipoli, with their impressive baroque architecture; Taranto, a bustling port city with a history dating back to the Spartans and known for its fresh seafood restaurants; the town of Otranto, where a chapel in the cathedral displays skulls of martyrs from a 15th-century Ottoman siege; and the scenic fishing town of Monopoli, with its beaches and castles.</p> <h3>Adriatic Coast and Sardinia</h3> <p>Small ships also visit Italy’s Adriatic Coast, including the historic Ancona, which has Roman ruins and beaches. Additional islands might appear on an Italy cruise itinerary, too, such as Sardinia, where the wild landscape affords hiking opportunities with views, and you can wander among medieval sights in the historic port city of Cagliari.</p> <h2>The best Italy cruises for every type of traveler</h2>

Amalfi Coast

Along the famed Amalfi Coast , ships visit Sorrento, overlooking the bay of Naples, and colorful Amalfi, dramatically backed by steep cliffs. Some itineraries also including the strikingly beautiful Positano. Smaller yacht vessels may sail directly to the fancy island of Capri (otherwise there will be a shore excursion, as with the larger ships). Among other shore choices in this region is a visit to ancient Pompeii.

Italy cruise itineraries often land at several ports on Sicily, and some itineraries circumnavigate the island. Each port has its own allure, including the city scene in Palermo; Syracuse, which showcases ancient attractions from when it was a prominent Greek city; Taormina, with its impressive hilltop location and Greek theater; and Lipari, which has a charming, tiny island ambience. In addition to striking landscapes, attractions include Roman and Greek ancient historic sights and views of Mount Etna, plus filming locations featured in The Godfather movies and in Season 2 of the HBO series The White Lotus . If while cruising Sicily your ship ventures to Stromboli, with its famous volcano, it will be from a safe distance—and if you’re lucky, in the dark when you can witness the lava flowing.

Increasingly popular on the cruise map are destinations in Puglia , a region of olive groves and national parks. Small ships call in the city of Lecce and town of Gallipoli, with their impressive baroque architecture; Taranto, a bustling port city with a history dating back to the Spartans and known for its fresh seafood restaurants; the town of Otranto, where a chapel in the cathedral displays skulls of martyrs from a 15th-century Ottoman siege; and the scenic fishing town of Monopoli, with its beaches and castles.

Adriatic Coast and Sardinia

Small ships also visit Italy’s Adriatic Coast, including the historic Ancona, which has Roman ruins and beaches. Additional islands might appear on an Italy cruise itinerary, too, such as Sardinia, where the wild landscape affords hiking opportunities with views, and you can wander among medieval sights in the historic port city of Cagliari.

The best Italy cruises for every type of traveler

<h3>Abercrombie & Kent</h3> <p><b>Itinerary: Hidden Treasures From Florence to Venice</b><br><b>Best for: Classic Italy cruise experience</b><br><b>Number of days: 11</b><br><b>Starting cost: $14,885 per person (including two hotel nights in Florence)</b></p> <p>Luxury tour company Abercrombie & Kent carefully curates its cruise itineraries with local guides on shore and with destination experts onboard. A&K has partnered with French line Ponant for a <a class="Link" href="https://fave.co/48LwNAn" rel="noopener">September Italy cruise</a> on Ponant’s diesel-electric ship <i>Le Bougainville</i>. This trip explores Florence, Rome, and Venice, stopping along the way on the islands of Sardinia and Sicily, and in Bari (the capitol of Puglia) and Ancona. Added bonus: a day on the French island of Corsica, the birthplace of Napoleon Bonaparte. The experience is limited to 148 guests, who can sip drinks with views in the ship’s underwater lounge.</p>

Abercrombie & Kent

Abercrombie & kent.

Itinerary: Hidden Treasures From Florence to Venice Best for: Classic Italy cruise experience Number of days: 11 Starting cost: $14,885 per person (including two hotel nights in Florence)

Luxury tour company Abercrombie & Kent carefully curates its cruise itineraries with local guides on shore and with destination experts onboard. A&K has partnered with French line Ponant for a September Italy cruise on Ponant’s diesel-electric ship Le Bougainville . This trip explores Florence, Rome, and Venice, stopping along the way on the islands of Sardinia and Sicily, and in Bari (the capitol of Puglia) and Ancona. Added bonus: a day on the French island of Corsica, the birthplace of Napoleon Bonaparte. The experience is limited to 148 guests, who can sip drinks with views in the ship’s underwater lounge.

<h3>Atlas Ocean Voyages</h3> <p><b>Itinerary: Valletta to Rome</b><br><b>Best for: food lovers</b><br><b>Number of days: 8</b><br><b>Starting cost: $3,499 per person</b></p> <p>Atlas Ocean Voyages, with its elegant small expedition ships, switches the focus from penguin-spotting in Antarctica to summer expedition cruises in Europe, including what the Portuguese-owned line calls “epicurean expeditions.” On the 196-passenger <i>World Traveller</i>, <a class="Link" href="https://fave.co/48FyoI2" rel="noopener">one such expedition from between Malta and Rome</a> adds the food angle to exploration of Sicily and the Amalfi Coast, with overnights in Positano, the dramatically positioned cliffside town with its labyrinth of staircases, and on the island of Capri. An expedition team will lead culinary explorations on the ship and ashore, such as visiting local markets and specialty tastings, culinary presentations, cooking demonstrations, and sampling wine.</p>

Atlas Ocean Voyages

Itinerary: Valletta to Rome Best for: food lovers Number of days: 8 Starting cost: $3,499 per person

Atlas Ocean Voyages, with its elegant small expedition ships, switches the focus from penguin-spotting in Antarctica to summer expedition cruises in Europe, including what the Portuguese-owned line calls “epicurean expeditions.” On the 196-passenger World Traveller , one such expedition from between Malta and Rome adds the food angle to exploration of Sicily and the Amalfi Coast, with overnights in Positano, the dramatically positioned cliffside town with its labyrinth of staircases, and on the island of Capri. An expedition team will lead culinary explorations on the ship and ashore, such as visiting local markets and specialty tastings, culinary presentations, cooking demonstrations, and sampling wine.

<h3>Azamara Cruises</h3> <p><b>Itinerary: Italy Intensive Voyage</b><br><b>Best for: More affordable Italy sailing</b><br><b>Number of days: 10</b><br><b>Starting cost: $2,320 per person</b></p> <p>Sailing round-trip from Venice on the upscale 684-passenger <i>Azamara Pursuit</i>, this “<a class="Link" href="https://fave.co/3ZKmyIt" rel="noopener">Italy Intensive Voyage</a>,” which sets sail in June 2024, takes passengers to Bologna, where optional excursions include a visit to the Ferrari Museum, and the historic Adriatic port city of Ancona, before cruising over to Kotor, Montenegro, with its impressive fjord approach and UNESCO-recognized Old Town. Heading south, you’ll stop by Taranto in Puglia and Sicily’s Giardini Naxos (near Taormina) and Palermo, before lingering in Amalfi, Sorrento, and Capri. There’s the bonus of a day in Rome (accessible from the port of Civitavecchia). It’s a packed itinerary and a great price.</p>

Azamara Cruises

Itinerary: Italy Intensive Voyage Best for: More affordable Italy sailing Number of days: 10 Starting cost: $2,320 per person

Sailing round-trip from Venice on the upscale 684-passenger Azamara Pursuit , this “ Italy Intensive Voyage ,” which sets sail in June 2024, takes passengers to Bologna, where optional excursions include a visit to the Ferrari Museum, and the historic Adriatic port city of Ancona, before cruising over to Kotor, Montenegro, with its impressive fjord approach and UNESCO-recognized Old Town. Heading south, you’ll stop by Taranto in Puglia and Sicily’s Giardini Naxos (near Taormina) and Palermo, before lingering in Amalfi, Sorrento, and Capri. There’s the bonus of a day in Rome (accessible from the port of Civitavecchia). It’s a packed itinerary and a great price.

<h3>Emerald Cruises</h3> <p><b>Itinerary: Highlights of Southern Italy</b><br><b>Best for: Intimate yacht experience</b><br><b>Number of days: 7</b><br><b>Starting cost: $6,120 per person</b></p> <p>Cruising with thousands or even hundreds of people is one thing; cruising around southern Italy on a luxury super yacht is something else completely. Sail on Emerald Cruises’ 100-passenger <i>Emerald Sakara</i> <a class="Link" href="https://fave.co/3ZOaAxM" rel="noopener">from Civitavecchia to Dubrovnik</a>, daydreaming in a designer daybed at the infinity pool when you’re not on shore exploring Sicily, the Amalfi Coast, Calabria (from the port city of Crotone) and Puglia. In Sorrento, an included guided tour of the city focuses on gelato. In Sicily’s Giardini Naxos, an optional excursion involves river tubing.</p>

Emerald Cruises

Itinerary: Highlights of Southern Italy Best for: Intimate yacht experience Number of days: 7 Starting cost: $6,120 per person

Cruising with thousands or even hundreds of people is one thing; cruising around southern Italy on a luxury super yacht is something else completely. Sail on Emerald Cruises’ 100-passenger Emerald Sakara from Civitavecchia to Dubrovnik , daydreaming in a designer daybed at the infinity pool when you’re not on shore exploring Sicily, the Amalfi Coast, Calabria (from the port city of Crotone) and Puglia. In Sorrento, an included guided tour of the city focuses on gelato. In Sicily’s Giardini Naxos, an optional excursion involves river tubing.

<h3>Lindblad Expeditions</h3> <p><b>Itinerary: Mediterranean Gems: Southern Italy and Sicily Aboard <i>Sea Cloud</i></b><br><b>Best for: Historic ship experience</b><br><b>Number of days: 10</b><br><b>Starting cost: $18,602 per person</b></p> <p>Passengers will immerse themselves in history as soon as they set foot on the 58-passenger <i>Sea Cloud</i> tall ship, built in 1931 for socialite Marjorie Merriweather Post and finance tycoon E.F. Hutton, and decorated with period antiques. Lindblad Expeditions is operating the vessel on several Mediterranean journeys in 2024, including this <a class="Link" href="https://fave.co/3LMPSZa" rel="noopener">Southern Italy and Sicily sailing</a>. There will be a Lindblad–National Geographic–certified photo instructor to help guests get perfect photos of the ship’s iconic sails and of the enchanting sights on an off-the-beaten-path itinerary to Puglia, Sicily, and the Amalfi Coast, sailing from Dubrovnik to Naples. Highlights include a private lunch at Castello degli Schiavi, an 18th-century castle used as a filming location in <i>The Godfather</i> movies.</p>

Lindblad Expeditions

Itinerary: Mediterranean Gems: Southern Italy and Sicily Aboard Sea Cloud Best for: Historic ship experience Number of days: 10 Starting cost: $18,602 per person

Passengers will immerse themselves in history as soon as they set foot on the 58-passenger Sea Cloud tall ship, built in 1931 for socialite Marjorie Merriweather Post and finance tycoon E.F. Hutton, and decorated with period antiques. Lindblad Expeditions is operating the vessel on several Mediterranean journeys in 2024, including this Southern Italy and Sicily sailing . There will be a Lindblad–National Geographic–certified photo instructor to help guests get perfect photos of the ship’s iconic sails and of the enchanting sights on an off-the-beaten-path itinerary to Puglia, Sicily, and the Amalfi Coast, sailing from Dubrovnik to Naples. Highlights include a private lunch at Castello degli Schiavi, an 18th-century castle used as a filming location in The Godfather movies.

<h3>The Ritz-Carlton Yacht Collection</h3> <p><b>Itinerary: Rome (Civitavecchia) to Valletta</b><br><b>Best for: Luxury experience</b><br><b>Number of days: 10</b><br><b>Starting cost: $10,600 per person</b></p> <p>You can be sure that the Ritz-Carlton Yacht Collection is going to deliver high-end resort cruising, and that’s certainly the case on the 298-passenger <i>Evrima</i>, where Moët & Chandon will flow freely as guests <a class="Link" href="https://fave.co/48FQ865" rel="noopener">sail from Rome to Malta</a>. Itinerary creativity is another bonus, as you explore the Amalfi Coast, Puglia, and Syracuse, the ship lingering in several ports so that you can go out on the town, with overnights in both Sorrento, where there is time to visit the emerald waters of the Grotta dello Smeraldo, and Taranto, with its white beaches and dolphin-spotting.</p>

The Ritz-Carlton Yacht Collection

Itinerary: Rome (Civitavecchia) to Valletta Best for: Luxury experience Number of days: 10 Starting cost: $10,600 per person

You can be sure that the Ritz-Carlton Yacht Collection is going to deliver high-end resort cruising, and that’s certainly the case on the 298-passenger Evrima , where Moët & Chandon will flow freely as guests sail from Rome to Malta . Itinerary creativity is another bonus, as you explore the Amalfi Coast, Puglia, and Syracuse, the ship lingering in several ports so that you can go out on the town, with overnights in both Sorrento, where there is time to visit the emerald waters of the Grotta dello Smeraldo, and Taranto, with its white beaches and dolphin-spotting.

<h3>Star Clippers</h3> <p><b>Itinerary: Amalfi & Sicily</b><br><b>Best for: Value</b><br><b>Number of days: 7</b><br><b>Starting cost: $1,930 per person</b></p> <p>Star Clippers’ Amalfi and Sicily itinerary on the 166-passenger <i>Star Flyer</i> sailing ship is the perfect combination of going with the wind and hitting key sights. The <a class="Link" href="https://fave.co/3F4i4D4" rel="noopener">itinerary is round trip from Civitavecchia</a> (near Rome), making this cruise a convenient and affordable add-on to your own exploration of Italy’s “Eternal City.” Set sail for Sicily (Messina and Lipari) and visit the Amalfi Coast (Sorrento and Amalfi). There’s the bonus of a port call in picturesque Ponza, an island in the Tyrrhenian Sea and very much not on the typical tourist path. When sailing, take in the breezes on the bowsprit.</p>

Star Clippers

Itinerary: Amalfi & Sicily Best for: Value Number of days: 7 Starting cost: $1,930 per person

Star Clippers’ Amalfi and Sicily itinerary on the 166-passenger Star Flyer sailing ship is the perfect combination of going with the wind and hitting key sights. The itinerary is round trip from Civitavecchia (near Rome), making this cruise a convenient and affordable add-on to your own exploration of Italy’s “Eternal City.” Set sail for Sicily (Messina and Lipari) and visit the Amalfi Coast (Sorrento and Amalfi). There’s the bonus of a port call in picturesque Ponza, an island in the Tyrrhenian Sea and very much not on the typical tourist path. When sailing, take in the breezes on the bowsprit.

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6 Sicilian hot spots you don’t want to miss

Consider this your go-to guide to the island’s cities..

Anna Staropoli

Sicily is having a moment, but where The White Lotus sparked curiosity, the island’s character keeps it alive. From Palermo to Catania , both heart and history infuse everything, from street corner stigghiole stands to centuries-old palaces. Every year or so, I visit Sicily: my grandfather’s and my past stomping grounds. Whenever the time comes to plan my trip, I’m torn between exploring new places in Italy and returning to my favorite island. But with boundless beaches, Baroque marvels, and all the arancine, Sicily—and its vast, varied cities—always wins.

Piazza dei Quattro Canti

Orient yourself in the Quattro Canti , which divides Palermo into four corners. In La Kalsa —my go-to neighborhood—artisan workshops, palaces-turned-museums, and Arab-Norman churches cluster. One standout, Palazzo Chiaromonte Steri , preserves the graffiti of Spanish Inquisition prisoners.

For postcard-perfect panoramas, the top of Palermo’s cathedral draws crowds, but I prefer the less-visited views from Santissimo Salvatore . When it comes to markets, however, the busier the better. You can’t miss lively, large Ballarò , though Vucciria beckons after the sun sets. I lived one street away and learned to sleep through the vibration of revelers, who turn the market into a communal, outdoor bar.

Where to eat: Start your day with a granita from Casa Stagnitta , or a tiramisu in Cioccolateria Lorenzo’s garden. Graze at the markets for lunch, but save room. Ai Bottai assembles a thorough pre-dinner apericena, where your drink comes with a platter of finger foods. For something heartier, Aja Mola serves fresh fish just a street away.

Hotel pick: Spend a night at the museum at Stanze al Genio —a bed and breakfast that houses nearly 5,000 majolica tiles. For a more traditional stay, consider Hotel Ambasciatori . The rooftop bar faces the mountains and makes my favorite Hugo spritz.

Tip: Base yourself in Palermo to swim at Mondello Beach ; gaze at Monreale ’s golden mosaics; and wander through Agrigento’s Valley of the Temples . You can also access Trapani—the gateway to Sicily’s Egadi Islands .

Pizza at Bastione & Costanza

Cefalù is only an hour from Palermo, but the romantic beach town begs to be savored, either in the water or while gazing at it. For the latter, head up La Rocca . The mountain trail intersects with ancient ruins and rewards hikers with coastline views—and the occasional clang of cowbell-clad goats.

Yet because my ideal day starts and ends along the beachfront promenade , I overlooked Cefalù’s cathedral until my third visit. Don’t make my mistake; the church contains some of Italy’s most significant, sparkling Byzantine mosaics.

Where to eat: As a beach town, Cefalù excels in small bites and large beers. For a more substantial meal, grab a table at Bastione and Costanza . I recommend any of the pizzas, which vary in dough thickness and toppings.

Hotel pick: Club Med Cefalù caters to activity-inclined travelers, with experiences that range from sailing trips to Vespa tours. Plus, the resort’s all-inclusive nature means you can sample Sicily’s full range of foods. If you’d rather make your own itinerary, book a room at B&B Agrodolce .

People walking outside the Ear of Dionysius at the Neopolis Archeological Park, Syracuse

In the Southeast, Syracuse is as Greek as Sicily gets. Of all the ruins, don’t miss the Neopolis Archeological Park ’s Ear of Dionysius . You can walk right inside the cave—which, indeed, resembles an ear—and listen to the echoes. Afterward, cross the bridge into Ortigia , Syracuse’s island center. Stroll along the edges of the city, but take the time to stop—or swim—at any of the seaside alcoves. When the sky turns golden, veer inland to linger in La Piazza Duomo .

Where to eat: Overlooking the Temple of Apollo , Caffè Apollo combines two of Sicily’s greatest prides in one perfect ricotta granita. Nearby, Caseificio Borderi makes mouthwatering sandwiches. Rather than design your own, give creative freedom to whoever's in charge.

Hotel pick: Sleep seaside at Algilà Ortigia Charme Hotel , a higher-end option with an interior as detailed as its facade. A less costly accommodation, B&B Marina di Ortigia has just four guest rooms and a rooftop terrace.

Val di Noto ’s Baroque towns

Noto Cathedral at sunset

Sicily’s major cities border the coast, but several UNESCO-recognized Baroque towns congregate inland in the southeast. My favorite, Ragusa , splinters into two cities of two elevations: the work of a 17th-century earthquake and rebuilding efforts. The descent from modern Ragusa Superiore to historic Ragusa Ibla suspends you above, then amongst, the hills.

Another golden city, Noto is as known for its Baroque architecture as its almond granita, made famous by institution Caffé Sicilia . (Yes, the granita alone warrants a visit.) If the cafe only just satisfies your sweet tooth, however, head to Modica —a chocolate wonderland masquerading as a town. Historic chocolate factory Antica Dolceria Bonajuto runs tours and tastings.

Where to eat: Although I could subsist on granita and chocolate, the area doesn’t skimp on the savory. Ragusa’s Taberna dei Cinque Sensi epitomizes Italy’s slow food movement. You can’t go wrong with any of the dishes, so long as you order a glass of Nero d’Avola.

Hotel pick: For a stay in historic Ragusa, the San Giorgio Palace Hotel provides easy access to the city. Yet for maximum serenity, drive straight for the hills, where Eremo della Giubiliana offers spa services and cooking classes.

Tip: If you’re not renting a car, Sicily’s public transit can prove unreliable, especially between smaller towns. Build some wiggle room into your itinerary for delays.

Close up of stalls at the Fish Market of Catania

In the shadow of Mount Etna, Catania is known as the “black city,” but through its dark architecture, a warmth emerges. I like to linger in Piazza Duomo , where the ornate basilica reflects the city’s grandeur. Just a few streets over, the open-air fish market bursts with energy and culture.

On a clear day, meander through Giardino Bellini for views of Etna. To see the volcano up close, consider an organized tour , which minimizes the stress of logistics. You can, alternatively, plan your own hike, or take a train around the volcano’s base.

Where to eat: With homemade noodles, La Pentolaccia makes my favorite pasta alla norma. I also suggest the horse meatball, a traditional—albeit controversial—food. Meanwhile, Pasticceria Savia is a one-stop shop for pastries, rice balls, and coffee.

Hotel pick : Airy bed and breakfast Il Leone Blu neighbors the Ursino Castle , while lower-priced B&B Liberty 900 ranks high in hospitality.

The Greek theatre and Mount Etna

Taormina is Sicily’s answer to luxury—best exemplified by the cable car descent to the Isola Bella , which translates to “beautiful island.” The city’s ancient theater maintains this theme of beauty; it’s notable not only for its ruins but also for its stunning Mount Etna backdrop.

In the evening, I love a passeggiata—a meandering stroll—along Corso Umberto , where the city hums with energy. As you walk, duck into nearby galleries, antique shops, and museums like Casa Cuseni . I own two watercolors from a Taormina street painter and have my eye on a map from art gallery L’Agorà .

Where to eat: On my last trip, I found myself at Arco Rosso three nights in a row. The cozy wine bar shines at aperitivo, with local wines and an assortment of bruschetta. For a fancier dinner, try Teatro 44 ’s pasta and seafood.

Hotel pick: If you want a mid-priced stay that doesn’t skimp on amenities, Hotel Ariston comes with a sprawling buffet breakfast—prosecco included—and outdoor pools. On the more lavish end, Hotel Villa Belvedere embraces all things serene and pristine.

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7 of the best small towns and villages to visit in Tuscany

Driving among the medieval towns dotted across the countryside is a quintessential tuscan experience, article bookmarked.

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Tuscany is famous for its rolling green hills

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Although Italy has no shortage of enchanting holiday destinations – the Amalfi Coast , Cinque Terre, Puglia and Sicily , to name just a few – there’s something particularly magical about Tuscany.

This is a region that often seems to be bathed in a soft golden light, with gently sloping hills and beautiful Italian villas nestled among olive groves, cypress trees and vineyards .

Although you could easily fill your days in the cities of Florence and Pisa, or exploring the narrow streets and central piazza of Siena, perhaps one of the greatest experiences in Tuscany is exploring the many medieval hilltop towns and villages that are scattered through the countryside.

From the famous towers of San Gimignano and charming Pienza to Greve in the wine-making region of Chianti, there are plenty of towns and villages to discover, all with their own unique charms and within easy driving distance of one another. Here are seven of our favourites.

San Gimignano

San Gimignano is one of the best known small towns in Tuscany – and for good reason. With its hilltop location, charmimg local restaurants and picture-perfect setting, it’s a favourite among tourists. Visitors can stroll through the medieval streets, stop in at one of the many small shops, gaze at the town’s impressive Duomo cathedral and visit the civic museum at the Palazzo del Popolo.

There’s a fun story behind San Gimignano’s famous towers. Between the 11th and the 13th centuries, the noble families who controlled the town believed their towers were a sign of wealth and power to their political and economic rivals, and so kept building more and more – it is believed that a total of 72 could be found in San Gimignano at its peak. Only 14 have survived, but they’re still rather impressive and give the town a palpable sense of history .

Read more on Italy travel :

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  • Palermo city guide: Best things to do and where to stay in the energetic yet charming capital of Sicily

Montalcino is an excellent choice for wine lovers – it’s well known for its brunello di montalcino and rosso di montalcino wines. The location in the hills of the Val d’Orcia gives it an even more rustic setting than other towns on this list. Visitors will find themselves surrounded by countryside dotted with cypress trees and flowers, as well as rolling olive groves and vineyards. Tourists can climb the fortress walls, amble through the winding streets and spend some time on the town’s Piazza del Popolo – but no visitor should miss the wine tastings which can be enjoyed in and around the town.

Pienza also lies in the Val d’Orcia, where gently rolling hills are populated by Renaissance towns, vineyards and medieval castles. The town itself is surrounded by medieval walls, inside of which is a maze of pretty cobbled streets lined with typical Tuscan houses. From the town you can enjoy amazing views over the hills and olive groves, and in the distance sits Mount Amiata.

All roads in this town lead to the Pio II plaza, with particularly picturesque streets including the Via dell’Amore and Via del Bacio. The town’s cathedral sits in this square, as does the Palazzo Piccolomini and Palazzo Borgia, which houses the town’s museum.

Greve in Chianti and Montefioralle

A visit to Tuscany is arguably not complete without a visit to Chianti, the region’s famous wine-producing area. Greve in Chianti is one of the more scenic towns in this part of Tuscany – it’s centred around the triangular Piazza Matteotti, the porticos of which hide vendors of various fresh produce.

In the foothills just below Greve in Chianti lies Montefioralle, one of the oldest villages in Tuscany. It’s still enclosed by its original defensive walls, and its (nearly) car-free centre is a great place for a relaxed stroll. The surrounding vineyards will likely be the focus of your visit, but be sure to climb up the hills to the highest point in the village where you can see the Santo Stefano church and take in a sweeping view of the vineyards, olive groves and cypress trees.

Volterra was once a mighty Etruscan city, but nowadays it is best known for Italian handicrafts and remnants of its medieval past. It is dominated by its Duomo along with the Palazzo dei Priori and 13th-century palazzo, though the 2,000-year-old Roman amphitheatre is another highlight. Remnants of its Etruscan past remain in the 5th-century Porta all’Arco walls and the Guarnacci Etruscan Museum, while the smaller Pinacoteca museum focuses on art from between the 14th and 17th century.

Pitigliano is located in the Maremma region near the Tuscan coast. It’s another hilltop town, and features rows of sandstone buildings built on top of volcanic red “tuff” stone. As well as enjoying wine tastings, tourists can amble through the mazy streets, stop for a drink or bite to eat around the lovely Piazza del Popolo, explore the palace-fortress of Palazzo Orsini (and its museum) and visit the Sette Cannelle fountain.

This town is also known as “Little Jerusalem” as a large Jewish population resided there until around the time of the Second World War, and there are several remnants of its religious history still present, from an old Jewish Quarter – now with a Jewish museum – to a gilded synagogue.

Pietrasanta

Pietrasanta still retains some of the artistic creativity that was associated with it in bygone times when artists such as Michelangelo frequented the town. Today it has one of the highest concentrations of art galleries in any Italian town, from the Favret Mosaici Artistici to the Flora Bigae gallery of contemporary art.

Pietrasanta is located very close to the coast, near upmarket resorts like Forte dei Marmi, and so is a town influenced by both local history and modern tourism. Away from the beaches, the highlights include the Duomo and the Rocca di Sala fortress, while an archaeological museum, marble quarry and yearly performing arts festival (named La Versiliana) are a little more off the beaten track.

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Old world sicily & malta, about this tour.

Explore Sicily and Malta – two island paradises nestled amongst the deep blue waves of the Mediterranean. Engage with Malta’s dynamic past on a leisurely 4-night stay. Explore Siracusa’s archeological heritage (UNESCO) with a guide. Spend three nights in Taormina, perched above the Ionian Sea. See Mount Etna from a different perspective on an off-road excursion. Discover how ancient traditions blend into modern society as you travel along timeless Italian and Maltese towns.

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10 Breakfasts

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While just about any month is great to visit Sicily and Malta, there are a few prime times of the year for the Old World Sicily & Malta tour. Here are some recommendations from our destination experts.

Winter: Malta’s winter climate ushers in balmy, days with little rainfall. In Sicily, it’s much milder than in other Italian cities this time of year, with the almond trees blooming in February.

Spring and Fall: Enjoy the perfectly mild climate of Malta outside the summer season and absent the crowds.

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Must-See Inclusions:

Explore Valletta (UNESCO), the capital of the Knights of Malta, a city “built by gentlemen for gentlemen.”

Pass by Baroque architecture and wrought iron balconies on a winding walking tour of Ragusa (UNESCO).

Spend three nights in Taormina (UNESCO) and explore its iconic Greek theater.

Cultural Experiences:

Soak up the island ambiance of Malta with a 4-night stay in Sliema.

Delve into Maltese culture during a tour of a traditional limestone village.

Ascend the sides of Mount Etna (UNESCO) in off-road vehicles.

Culinary Inclusions:

Explore the flavors of Maltese cuisine during a family-style dinner at a local band club.

Pause for a Sicilian cappuccino and pastry breakfast at a local “bar.”

Visit a family-owned organic herb farm and enjoy a lunch flavored with delicious aromatic plants.

  • Ferry to Sicily
  • Aromatic Herb Farm Tour
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  • Mount Etna Off-Road Excursion

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During your stay at the Lands End Urban Boutique Hotel in Sliema, you may choose to enjoy views of Marsamxett Harbour and Valletta by upgrading your accommodations to a sea view room. Upgrade available at the above cost per person, double. Please inquire about this upgrade at time of booking.

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Hotel-NH Collection Taormina

During your stay at the NH Collection Taormina you can choose to upgrade your room to a Deluxe Sea View with Spa access, providing the opportunity to enjoy views of Taormina's rooftops and the Mediterranean Sea. Upgrade available at the above cost per person, double. Please inquire at time of booking.

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Embark on a full day exploration of the isle of Gozo, the second largest island of the Maltese archipelago. A short ferry ride takes you to across to Malta’s greener neighbor, home to the Ggantija temple complex (UNESCO), which is older than Stonehenge. Uncover this UNESCO site with a local expert and learn about Gozo’s 7,000 years of history. Pause for lunch at a local restaurant before enjoying a panoramic drive highlighting the many captivating legends of Gozo. Discover for yourself why the great epic poet Homer identified Gozo as the home of the nymph Calypso who kept Ulysses captive here for seven years.

Spend your morning in Mdina, the Silent City. Your tour begins with an exploration of the site that is traditionally identified with Saint Paul’s Grotto, where legend holds that this is where Paul the Apostle stayed when he arrived on the island in 60 CE. Then, set off on foot through the narrow, winding streets of Mdina for an intimate look at Malta’s ancient capital, absconded in the countryside and protected for centuries before the arrival of the Knights of Malta.

Journey to Sicily’s Baroque Valley, known for its ornate historic architecture. Discover UNESCO World Heritage sites in Scicli and Modica. The town of Scicli dates back to the 3rd century BC, home to a number of centuries-old churches. Visit a local farm for brunch to learn about two local specialties: ricotta cheese and sausage. The hilly city of Modica, dating back to the 2nd century BC, is renowned for its baroque architecture and breathtakingly detailed facades. Taste Modica’s historically rooted artisanal chocolate, based on flavorful Aztec recipes of millennia ago. This tour will immerse you in the alluring culture and history of the Baroque Valley.

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