self guided tour of old san juan

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Self-Guided Walking Tour of Old San Juan

One of the best ways to see the city of Old San Juan, Puerto Rico is to walk. Stroll upon the blue cobblestone streets of this oldest city in America and see pastel-colored colonial architecture, historic forts, quaint museums, monuments, and charming plazas with cafes and restaurants.

The city is layered with hundreds of years of Spanish, Taino, and African influences. Take this self-guided walking tour of Old San Juan and immerse yourself in the culture and cuisine of this charming city.

Links to Google Maps are included to help you along your journey.

Welcome to Old San Juan!

Start your walking tour at calle marina.

This walking tour starts at Calle Marina , which is where the cruise ships dock. If you are driving into the city, there’s a reasonably priced parking garage on PR38 . Park in the garage and walk toward the waterfront. Enjoy the beautiful view of the bay!

Plaza Darsenas & Casita de Rones Bar

From the marina head west, with the bay on your left, to Calle Comercio. You will come upon Plaza Darsenas and the Casita de los Rones bar . It serves as a promotion center for the rums of Puerto Rico. Make a stop and grab a refreshing rum cocktail or a bite to eat.

Plaza de Hostos

Continue walking towards Plaza de Hostos . A bust of Eugenio María de Hostos stands proudly. Hostos was an avid supporter of the independence movement for Puerto Rico and Cuba. He dedicated his life to educational causes and advocating women’s is cbum natural rights to higher education.

What are the blue stones?

You may have noticed you’ve been walking on blue stones. Brought over on Spanish ships, they are adoquin , cast from furnace slag, and used as ballast on the ships. The characteristic blue color comes from age and moisture.

El Paseo de la Princesa

Continue strolling on the path toward San Juan’s most beautiful promenade, El Paseo de la Princesa . Originally created in 1853, the Paseo, features a broad brick walkway. It leads visitors through a pleasant tree-lined sculptural and garden showcase.

Look up and see the remains of the original city walls. La Muralla, a UNESCO World Heritage Site is nearly 400 years old. By 1873 masonry walls fully encircled the city and the fortification defended the entire islet. It was considered one of the best fortified cities in the Caribbean and consisted of lookouts and defensive positions.

On weekends, vendors sell local art, handmade jewelry, fried treats, and piragua , a shaved-ice made with tropical fruit syrup.

Puerto Rico Tourism Company

The Puerto Rico Tourism Company will be on your right. This building served as the prison from 1837 to 1960 and visitors can view the original jail cells located in the back courtyard.

Raices Fountain

Along with the lovely views of San Juan Bay you will see the beautiful Raíces or Roots Fountain . The fountain celebrates Puerto Rico’s rich cultural diversity and historical heritage. Sculpted by Spanish artist, Luis Sanguin, Amerindian, African, and Spanish peoples are represented.

Bacardi Factory

Look across the bay you’ll see a few wind turbines spinning. That’s the  Bacardi Rum Factory . To visit the Bacardi Factory from Old San Juan, ride the La Lancha Ferry on Pier 2 to Catano . Continue to the Bacardi Factory by taxi.

Crecimiento Sculptures

Follow the walkway as it bears to the right. A collection of bronze sculptures sit along the outside of the city walls called ‘Crecimiento.’ These are the creation of Carmen Inés Blondet in 1996 and represent the affirmation of life.

The shapes, rising from the ground, convey the idea that the fragility of growth is only an impression and what is truly important has to be eternal.

Queen Isabella Sculpture

Continue following the pathway and view the sculpture of Queen Isabella I of Spain in a courtyard next to the city wall. It’s shaded by a stately ficus tree.

La Puerta de San Juan

As you continue to follow the path you will come upon an immense red gate or La Puerta de San Juan . Build between 1634 and 1638, when the wall was built around the entire city, this massive door was closed at night to protect the city and its inhabitants.

Out of the three that were built, this is the only one that stands to this day. As you walk through the gate, notice the 15-feet thick walls.

A blessing, at the top of the gate, to all visitors as they pass through: “ Blessed is he who comes in the name of the Lord .”

Caleta San Juan

Walk through the gate and continue straight on San Juan Street or Caleta San Juan . Notice the colors and architecture of these 400-year old homes. The beautiful Moorish title and hidden courtyards make this my favorite street to take a stroll.

Cathedral de San Juan Bautista

At the top of San Juan Street is the graceful gothic Cathedral de San Juan Bautista   or the Cathedral of Saint John the Baptist. It is the second oldest church in the western hemisphere and oldest church on US soil. The history of the church begins in 1521 with the beginnings of the Spanish colonialization of the island.

The tomb of Ponce de Leon, the first governor of Puerto Rico is housed in this church. A Spanish conquistador, he led the first European expedition for gold to the Americas in addition to a small island to be later named, Puerto Rico. It was in 1509 he took office as the first Governor of Puerto Rico by appointment of the Spanish crown.

El Convento Hotel

El Convento Hotel is on the diagonal corner of the cathedral.

There have been numerous sightings of ghosts in the guest rooms over the years at El Convento Hotel. A Carmelite convent in the past, the popular ghost story revolves about Doña Ana de Lansos y Menéndez de Valdez, the founder.

Doña Ana was its first mother superior, and many say she never left. She and her nuns walk the halls, it has been reported. It is said that the swishing sound of their robes echoes through this hotel, even centuries after Doña Ana’s death.

El Bate bar

Head up the hill to Cristo Street or Calle de Cristo . If you’re thirsty, stop into El Bate , a little gem, with graffiti-covered walls and business cards hanging from the ceiling. Reasonably priced drinks, this place is a welcome respite from the heat.

San Jose Church

Continue walking up Calle Cristo and on the right is the oldest church in San Juan, the San Jose Church .

Built in 1532, it is one of the finest and oldest examples of Gothic influenced architecture built by the Spanish in the New World. It has recently been renovated.

Institute of Puerto Rican Culture

As the road bears to the left, the Institute of Puerto Rican Cultur e will be on the right. This museum houses the largest collection of Puerto Rican paintings from the eighteenth century to the 1960s.

El Totem Telurico & Plaza del Quinto Centario

Continue walking towards the left and you will see a plaza with a totem pole or El Totem Telurico .  This is Plaza del Quinto Centenario .

In 1992, to honor the 500 year anniversary of Columbus’ first voyage to the Americas, artist Jaime Suarez created this totem with clay. The clay is from different locations of the Americas, signifying the origins of the people .

Look out toward the ocean and you will see El Morro Fort in the distance.

El Morro Fort

A National Historic Site, completed in 1589, El Morro Fort is a stunning six-level fortress. It successfully protected the city from sea invaders.

The three flags waving at the top commemorate Puerto Rico, the US, and the Spanish military. Spectacular views and interesting historical items make this a fascinating place to visit. On weekends you’ll see families flying kites on the lawn.

The colorful neighborhood known as La Perla is located along the ocean to the right of El Morro. Community leaders have been making efforts toward the growth and development of what has for generations been one of the most underserved and economically disadvantaged sectors of San Juan.

This colorful barrio is where the filming for the pop hit “Despacito” took place. Please note that this is a local neighborhood, not a tourist attraction, so respect the privacy of those who live here.

Santa Maria Magdalena de Pazzis Cemetery

Before you reach El Morro, you will see the beautiful Santa Maria Magdalena de Pazzis Cemetery is the final resting place of many of Puerto Rico’s most prominent natives and residents ; artists, politicians, musicians, and painters.

If you plan to visit the cemetery it can be accessed by walking on Calle Norzagaray to the parking garage located underneath the Plaza del Quinto Centenario . Continue on Calle Del Cementerio and through the underground tunnel to reach the cemetery’s entrance.

Plaza de Beneficencia

In the plaza is a statue in honor of Eugenio Maria de Hostos. Importantly known as “The Great Citizen of the Americas” he was an advocate for Puerto Rico’s independence and an educator, lawyer, philosopher, sociologist, and writer.

Plaza de Ballaja & Museo de las Americas

To fully explore the attractions on this street, you’ll need about 2 hours if you were to visit both museums.

Museo de las Americas

Continue to the  Plaza de Ballaja  and see the  ballajá  or military barracks. Built in 1854 for the Spanish troops and their families. This building is home today of the Museo de las Americas containing pre-Columbian to modern art from the Americas.

Casa Blanca Museum

Continue walking and tucked on the southwest end of Calle Beneficencia and San Sebastian Street on the right, is Casa Blanca , built in 1521 for Juan Ponce de Leon and his family. It is the oldest house on the island. Visitors can tour the lovely gardens, mansion living spaces, a display of artifacts, and historic information.

Side Trip to La Factoria Bar

If you want to make a stop to the famous La Factoria Bar , don’t turn on Calle Sole just yet. Stay on San Sebastian Street and walk 2 blocks. La Factoria is rated as one of the worlds 50-best bars in North America. A labyrinth of six unique rooms, each with different menus and themes, cater to guests looking for a slightly different experience. 

From San Sebastian Street turn onto Calle Sol . Bursting with brightly painted houses and flowers, it’s a favorite of mine. A street that’s really a staircase. Now that’s unusual!

La Rogativa statue

At the bottom of Calle Sol, you’ll see  La Rogativa  statue, made by Lindsay Daen out of bronze. Rogativa means procession. This statue was created to celebrate a famous procession of faith in history.

When the British were about to attack the Spanish army in 1797, the Bishop and towns-women came up with a brilliant plan to protect the city. They held a procession, and s ubsequently, the British gave up the attack thinking the women were Spanish army reinforcements.

Across the street from La Rogativa, there’s a sign that says “limbers .” Next to it there is a small hallway and gated door. Run by a local family, they’ve been selling these sweet-fruit flavored ice treats for years. If no one is at the window, just knock loudly or call out a greeting.

Cristo & Forteleza Streets

Go up Las Monjas Street to Cristo Street . On Cristo Street, turn right. Cristo and Forteleza Streets are the main shopping areas. Outlet shops, Puerto Rican handcrafts, unique souvenirs, high-quality jewelry, and artwork can be found here.

La Forteleza

At the very end of La Forteleza Street, is the official residence of the Governor of Puerto Rico. La Forteleza , built to defend the harbor of San Juan is the oldest executive mansion in continuous use and a UNESCO World Heritage Site.

Capilla del Santo Cristo

Around the corner from La Forteleza, you’ll see the Capilla del Santo Cristo. Believers who come to the chapel seek miracles for physical illnesses.

The legend says that Baltazar Montanez, in 1753, took part in a traditional horse race, lost control, and plunged off the cliffs. The Spanish Secretary of Government, Don Mateo Pratts, cried out, “ Christ of Good Health, save him !” The young rider, lived. He was miraculously saved, they believed! That same year Montanez built the small chapel on the exact spot where Montanzez fell over the cliff.

Over the years believers have brought tiny silver ornaments, each one representing some ailing part of their body. These small “Milagros,” decorate the walls. They represent the cause of pain for the pilgrim. The church is open on Tuesdays and religious days. 

El Parque las Palomas

Next to the chapel on Calle de Tetuan, is Parque las Palomas or Pigeon Park. Here you can purchase bird food and feed the hundreds of pigeons that flock in the park.

You can choose to END your walking tour here, or continue to on to Fort de San Cristobal, which will put you near the parking garage on PR38.

Fort de San Cristobal

If you wish to visit Fort de San Cristobal , follow these directions from the Parque Las Palomas.

It should be noted that this fort is brilliantly constructed with a number of different units. Connected by tunnels, if one part is invaded, each unit is self-sufficient. In the dungeon, you can see some of the prisoner drawings on the walls. Be sure to take in the beautiful views of the Atlantic Ocean.

The self-guided walking tour of Old San Juan has come to an end.

We hope you enjoyed wandering the blue cobblestone streets with perhaps a piragua in hand. What did you think of the stunning architecture? Did you marvel at the 15-foot thick gate? Were you able to explore one of the incredible forts?

Old San Juan is a perfect place for a self-guided walking tour. With a myriad of historical sites and rich architecture, it’s a perfect way to spend the day.

More things to do in Old San Juan:

Take a sunset sail in old san juan bay.

Boulevards and Byways is a participant in the Amazon Services, LLC Associates, and Partner Viator Program s. T he affiliate advertising program provides a means to sustain this blog by linking to affiliate sites at no extra cost to you.

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Somto Seeks

Navigate the world with confidence

A Self-Guided Walking Tour of Old San Juan with Map

October 13, 2019 By Somto Ugwueze 8 Comments

Last updated on April 1, 2023

The streets of Old San Juan were practically built to be strolled for hours. With colorful, Spanish colonial architecture, picture-perfect corners, and mesmerizing views of the Caribbean Sea, you’re bound to have at least a few awe-inspiring moments during your tour of this historic city. Founded in 1521 by Spanish conquistadors, this port city has long been the cultural and commercial hub of Puerto Rico. It is home to some of the country’s most important landmarks, from fortresses to art galleries. Old San Juan is a charming neighborhood at the heart of the city with cobblestone streets, brightly-colored buildings, a plethora of bars and restaurants, and a whole lot of soul. This post will show you how to put together your own walking tour of Old San Juan and experience the must-see sites in the city. It includes a map so that you can follow along on your phone.

Disclosure: This post contains affiliate links, as explained in my disclosure policy

Time required for a tour of Old San Juan

Old San Juan is a compact area so this tour would take you about 60 minutes if you simply walked to each location without stopping. I would budget about 3-4 hours to give you enough time to take in the sites, tour the historic buildings, and enjoy the food. 

Items to bring with you

• Comfortable shoes – some parts of the tour are hilly so it’s a great idea to wear running shoes or something that won’t kill your feet after three hours of walking and climbing fortresses. This is completely up to you. I wore sandals and was mostly fine, except when it came to climbing steep concrete. Next time, I’ll wear definitely wear tennis shoes. 
• Water – stay hydrated, my friends!
• Snacks – pack some fruit, a granola bar, or my go-to travel snack, the WanderBar , a protein bar made specifically for travelers and frequent flyers. I can’t get enough of the Cocoa Crunch flavor.
• Map or GPS – Google maps, Apple maps, or whatever works best for you. Puerto Rico is a US territory so your phone service from any major US carrier should work just fine.
• Camera – you can use your phone camera, but a DSLR will capture those picturesque streets so much better! I always recommend the Nikon D3400 for beginners.

Old San Juan Walking Tour with Map for First-Time Visitors

The best sites to see, food to eat, and things to do in Old San Juan

Castillo San Cristobal

We’ll start at Castillo San Cristobal, the largest fortress that the Spanish built in the New World. A UNESCO World Heritage Site, this fortress is part of the San Juan National Historic Site , an area that includes fortresses, bastions, and the old city wall. Castillo San Cristobal was built in 1783 to protect the city from attacks when other European powers were trying to take over. 

You need a ticket to tour the inside of the fortress, but there’s an outside area with bastions overlooking the Caribbean Sea that anyone can visit. The ticket is $7 and is valid for two days to allow you to see other parts of the San Juan National Historic Site. 

There are three levels to this fortress: the lowest level, the main firing battery, and the observation deck at the top. To get into the fortress, you have to go through some dingy tunnels at the lowest level. Along the way, there are dimly lit rooms, including a dungeon where prisoners were kept for execution. It was creepy, to say the least. 

Once you get past the tunnels, then everything brightens up – literally. You arrive at the main firing battery with rooms on the periphery that overlook the city. There are plaques explaining what the rooms were used for. Lastly, there’s the top level of the fortress, with breathtaking views overlooking the city. I spent a lot of time here just taking in the scenery.

You can purchase your ticket at the San Juan National Historic Site office or call +1 787 729-6777 . The fortress is open every day of the week from 9 am to 6 pm.

Address : 501 Norzagaray Street San Juan, PR 00901 Hours : 9 am to 6 pm every day Price : $7

Calle de La Fortaleza

Calle Fortaleza is a shopping street in Old San Juan, located by the governor’s mansion. There are tons of little shops and restaurants here. This street used to be an Instagram hotspot when there were umbrellas floating at the top. When I visited San Juan in Old San Juan in July 2019, the umbrellas were unfortunately no longer there. The street was barricaded during my visit to San Juan because of protests against the government due to an political scandal. Not going to complain. People’s livelihoods are more important than my Instagram photos. That said, the umbrellas could be back again, as they are a major tourist attraction. I’ll have to confirm when I visit again.

Address : Calle de la Fortaleza San Juan, 00901, Puerto Rico Hours : 24 hours, 7 days a week Price : Free

La Fortaleza

La Fortaleza, also known as Palacio de Santa Catalina, is the official residence of the governor of Puerto Rico. Located at the base of Calle de La Fortaleza, it is the oldest, continuously used governor’s mansion in the western hemisphere. This blue building sits on a fortification by the Caribbean Sea that was built by the Spanish in the 16th century to protect the city against foreign attacks. You can take a free 30-minute tour of the interior, courtyards, and gardens every weekday from 9 am to 4 pm. To book a tour of La Fortaleza before you arrive in San Juan, you can email [email protected] or call +1 (787) 721-7000. Just can also arrive in person at the tourist office next to the mansion and book your tour, although same-day availability is not guaranteed. I didn’t know you could tour this building when I visited so I’m bummed! Now you know. 

Address : 54 Calle Fortaleza Edificio de la Real Audiencia San Juan, PR, 00901 Requirements : Must be at least 21 years and have a valid photo ID Hours : 9 am to 4 pm Price : Free

El Batey Bar

I was looking for some cheap mojitos and found this place on Yelp. When I walked in, I felt like I had stepped into some kind of punk rock tattoo parlor. That’s the vibe of this place – dimly-lit and dingy. With the somewhat pretentious writings on the wall, like ‘Prohibido Joder,’ and “Donald Eres Un Pendejo,” (not that I disagree with this statement), I didn’t have a good feeling about the place at first. 

But it turns out the mojitos were good and cheap. Also, the bartender, Javier, engaged me in a conversation for like an hour. Then, I ended up chatting with some locals at the bar, too. So I ended up liking this bar after all. It’s a great place to unwind and maybe meet new people.  El Batey is known for its casual atmosphere, politically incorrect posters, and affordable drinks.

Address : 101 Calle del Cristo, San Juan, 00901, Puerto Rico Requirements : Must be at least 21 years and have a valid photo ID Hours : 3 pm to 12 am every day Price : $3-$10

San Se Marisquería Bar de Tapas

San Se Marisqueria is a tapas bar-restaurant located down the street from the co-living community, Outsite San Juan, on Calle San Sebastian, from which it gets its name. This is by far the best restaurant in Old San Juan where I had the privilege of dining. I would recommend their Mofongo , a signature Puerto Rican dish consisting of mashed plantains, and their impeccably-seasoned Pulpo , or octopus (shown above). They are both unbelievably delicious! I’m sure the other items on the menu are equally so.

There is also a bar area serving cheap piňa coladas, mojitos, and other cocktails, which are around the same prices as other San Juan establishments. The food, though, is more expensive than at your average Old San Juan restaurant, but I think this place is definitely worth a visit. You can order takeout, but there’s no delivery.

Address : 152 Calle de San Sebastián, San Juan, 00901, Puerto Rico Hours : 3 pm to 2 am every day except Tuesday, when it’s closed Price : $3-$10

Calle Imperial

Calle Imperial is one of the iconic streets in Old San Juan with a flag of Puerto Rico on the wall. This flag is no ordinary mural; it has cultural significance. Known as Callejon de la Puerta Bandera, it is a symbol of Puerto Rican identity and pride and one of two flag murals in Old San Juan. The other one, located on Calle San Jose, is black and white. Calle Imperial is one of the most iconic places to snap a photo in San Juan. I wanted to get a photo of myself here and waited for someone to walk by. No one did so I just took a photo of the wall. The struggles of solo travel. Next time, I’ll be sure to take a tripod!

Address : Calle Imperial San Juan, 00901, Puerto Rico Hours : 24 hours, 7 days a week Price : Free

Castillo Felipe del Morro

Further west of Castillo San Cristobal is another fort called Castillo Felipe del Morro, simply known as El Morro. This fortress is also part of the San Juan National Historic Center. It has six levels which were built over the course of 200 years, starting in the 1500s.  This place has so much history, it will take you at least 90 minutes to fully tour and appreciate all the parts, from the dungeons in the lower level to the narrow stairwell that leads to the top level to the canons on the roof.

El Morro was one of the original fortifications built by the Spanish to protect San Juan from foreign invaders. Today, it’s popular among locals and tourists alike. The different levels, particularly the higher ones, offer incredible views of the Caribbean Sea and the entire city of San Juan. All around the structure, you’ll find many garitas , or guard posts, which are a great place to snap a photo. 

The best way to experience El Morro is to do a guided tour, like this guided tour of El Morro with an entry ticket that includes stops at other must-see places in Old San Juan. This tour is organized by Get Your Guide, a tour operator I’ve been using since 2016. I love how deeply informative and engaging their tours are, from Spain to China. I always leave their tours with tons of notes on my phone. The local tour guides they employ are knowledgeable and friendly.

Address : 501 Calle Norzagaray, San Juan, 00901, Puerto Rico Hours : 9 am – 5 pm every day Price : $10

Paseo de la Princesa

Paseo de la Princesa, which translates to Princess Promenade, is a pedestrian walkway by the San Juan Bay. Located in the historic district of Old San Juan, this picturesque promenade was built in 1853. It has undergone various renovations since then. You’ll take in breathtaking views of the San Juan Bay on one side, with the waves from the Caribbean Sea crashing against the shores. On the other side, you’ll get a good look at the majestic fortifications that were built centuries ago to protect the city from invasion.

Beyond the views, you’ll find a long line of street vendors selling everything from empanadas to handmade crafts to beaded jewelry. There is also an famous work of art, the Raíces Fountain, that features paintings of the different ethnic groups that make up Puerto Rican society – the African-descended people, the indigenous Taino people, and the Spanish conquistadors. This promenade is the perfect place to go for a stroll in the afternoon, people watch, and go souvenir shopping.

Address : Paseo de la Princesa, San Juan, 00901, Puerto Rico Hours : 24 hours, 7 days a week Price : Free

Catedral de San Bautista

Catedral of San Juan Bautista, also known as the Cathedral of Saint John the Baptist, is the second-oldest cathedral in the Americas. Completed in 1540, this Roman Catholic cathedral finest examples of Spanish colonial architecture. It features a mixture of Gothic and Baroque architecture, with an ornately-decorated altar made of gold. This towering cathedral has played a pivotal role in the cultural and spiritual life of Puerto Ricans for centuries, with many weddings, baptisms, and even state occasions taking place here. The Spanish explorer Juan Ponce de León is also buried at this cathedral. There are many churches in San Juan but Catedral de San Bautista is perhaps the most important. That makes it a must-see on your visit to Old San Juan, even if you’re not Catholic. The church is open to the public for free.

Address : 151 Calle del Cristo, San Juan, 00902, Puerto Rico Hours : 9 am – 4 pm every day Price : Free

Plaza de Armas

Plaza de Armas is the main plaza, or public square, in Old San Juan. Originally built as a training facility for the Spanish military, the plaza is now a a place of leisure. Tourists and locals alike gather here to enjoy concerts, festivals, and other cultural events. There are also a few notable structures at this plaza, including a a statue of the Spanish explorer, Juan Ponce de León and a statue of King Juan Carlos I of Spain. At the center, you’ll find a fountain with statues of religious and historical figures. This plaza is a great place to end your tour of San Juan. In the vicinity, you’ll find the San Juan City Hall and the Department of State building of Puerto Rico. You can sit down, relax, and bird watch before returning to your accomodation.

Address : FV8M+48H, San Juan, 00969, Puerto Rico Hours : 24 hours, 7 days a week Price : Free

Want to tour Old San Juan with a local guide?

While I’m a huge fan of self-guided walking tours, I also know the value of having a local guide show you around their city and explain what you are looking at. That’s why I’d recommend doing at least one guided tour of San Juan with a local operator in addition to your own self-guided tour.

One of the perks of doing a guided tour with my favorite tour operator, Get Your Guide, is being able to skip the long lines. If you wait until you arrive in San Juan to buy your tickets, you may be waiting for a long time, especially during the peak summer travel season. With a guided tour, you also get to learn directly from a local about the culture and history of San Juan, allowing you to better appreciate the sites, food, and other attractions. Below are the Get Your Guide tours I’d recommend in Old San Juan.

First, we have a foodie walking tour of Old San Juan that will give you a taste of Puerto Rican cuisine. A local guide will take you to the must-try restaurants in Old San Juan, where you’ll sample 10 delicious bites. You’ll also participate in a culinary class, where you’ll learn how to make the classic mofongo . The 3-hour tour comes with a bonus rum cocktail so that you can try Puerto Rico’s specialty drink.

The second tour I’d recommend is a sunset walking tour of Old San Juan . The sunsets in San Juan are something special, and you’ll get epic photos of the city at this time of the day. During this tour, a local guide will take you to historic places that aren’t included in this self-guided walking tour, such as the iconic Plaza Colón, Plaza de la Barandilla, and the ancient Palacio de la Intendencia. You’ll also discover the urban legend and mystery behind a chapel known as Capilla del Santo Cristo de la Salud. This 2-hour tour will fully immerse you in Puerto Rican culture and history.

Last but not least, it’s a good idea to get off the island and take in the whole scenery from a sailboat! This 90-minute sailing tour of San Juan is one of the best ways to experience the city. You’ll board a topsail and cruise around Old San Juan, taking in the city from a different vantage point. The sailing adventure comes with complimentary drinks, including rum, of course, so that you can unwind while you spot El Morro, La Fortaleza, and other iconic structures in the city. This would be an epic way to conclude your visit to San Juan.

Travel Resources I Love

CabinZero 36L Backpack – this trusty backpack has has been my go-to luggage for both domestic and international trips since 2018. I’ve used dozens of backpacks over the years and keep coming back to this one. I almost never check in luggage so I need a carry-on bag that is spacious, sturdy, and comfortable, with a laptop compartment. The Cabin Zero 36 L fits the bill. The size makes it small enough for a weekend getaway and big enough for a month of backpacking in Europe. The bag also comes with a tracker in case it gets lost. How convenient! Check out my complete review of the backpack.

Travel WiFI Pocket WIFI Device  – With portable WiFi, you can say goodbye to ridiculous roaming charges and SIM cards for good. I’ve been using the Travel WiFi Portable Hostspot device for years and love the peace of mind it gives me. The device provides 3G-4G WiFi for at least 6 hours and works in 100+ countries. In my experience, it lasts 9 hours. It also works in a variety of landscapes and terrains. I even filmed a Facebook Live from a boat in the Atlantic Ocean using my device. I can also use Google Maps, request an Uber, call my mom, and do tons of other things I couldn’t do before. Quick tip: turn off the device when you’re not using it so that the battery can last longer.

Booking.com – Booking.com is my go-to website for booking discounted accommodations around the world.  What I love most about Booking.com is the variety of properties you can find, from luxury apartments to treehouses to university housing. It’s hard to beat the insanely low prices. The website also has a flexible cancellation policy, which is great if things come up or you change your mind. 

For more travel product recommendations, check out my travel essentials page .

One more thing: if you enjoyed this post, please share it!

Somto Ugwueze

Hi! I'm Somto. Two years ago, I stopped making excuses, ditched my indecisive friends, and started booking flights. Today, I'm a full-time solo traveler on a mission to inspire young women to seek new adventures.

@somtoseeks

Reader Interactions

January 10, 2020 at 12:43 pm

I just got back from Puerto Rico shortly before Christmas 2019. Visited beautiful Old San Juan, with it’s lovely blue cobblestone streets. You forgot to mention their love of gatos! The cats roam the area and are fed by those that live there. ❤️

July 19, 2020 at 9:51 pm

Hi Peggy, yes, I forgot to mention those gatos! I loved seeing all the cute cats roaming around.

February 3, 2020 at 4:15 pm

Isn’t there a walk outside the walls of the city?

March 9, 2021 at 1:18 am

This is AMAZING!!!! It’s absolutely perfect, exactly what I’ve been looking for! THANK YOU!!! I never ever ever write comments/reviews on websites, but I absolutely had to for this. I’m with a group of 11 friends who wanted to see Old San Juan but didn’t plan anything specific, and I didn’t want to waste the whole day going back and forth. Having this all set up in order is going to save our lives! Thank you!!!

April 23, 2021 at 5:04 pm

Hi Auria, I’m overwhelmed that you found this guide helpful. Keep visiting to find more useful content dedicated to travelers!

June 2, 2021 at 11:42 am

Thanks for creating this blog! It was just what I needed. I was asked to come to Puerto Rico at the last minute for work and decided to bring my 15,16, and 20-year old children. We knew we wanted to visit Old San Juan but didn’t know what to do. Your blog came in handy! We didn’t hit every spot but definitely enjoyed our time. As an update for anyone reading the comments, the tour tickets are now $10 for anyone over 15. 15 and younger are free! Also, there was a food truck near El Morro selling non-alcoholic piña coladas. My children said they were delicious! Keep inspiring us through your travels. You are appreciated!

May 1, 2022 at 8:33 am

Very informative article . Thank you for the order. Will be visiting these places ❤️

March 1, 2023 at 11:04 pm

Thank you for writing this blog!! Very helpful! I am planning a trip with my family. I can’t wait to visit Old San Juan and Puerto Rico! It’s our first time.

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A Self Guided Walking Tour of Old San Juan

If you’re looking for an Old San Juan self-guided walking tour itinerary, you’ve come to the right place! Old San Juan is one of the most interesting cities in the USA.

Many cities in the United States have old towns. These can loosely be defined as colonial era towns that have kept their historical charm. There are quite a few scattered around the US. But perhaps the most spectacular of these old towns can be found in the US territory of Puerto Rico.

Old San Juan is the oldest – and in my opinion most beautiful – of all the historic old cities in the US. Founded by the Spanish in 1521, it’s a walking museum. Here we will cover a full day’s self guided walking tour of Old San Juan! 

Old San Juan – What You Need to Know

A brief history of old san juan, puerto rico , your self-guided walking tour of old san juan, avoiding the crowds in old san juan, eat like a local, outside old san juan , old san juan – faqs.

Note: this article contains affiliate links, which means that should you purchase something or get a quote through them I may make a small commission at no additional cost to you. This helps keep the site running with up to date information. I do not represent GetYourGuide, Booking.com, or Rentalcars.com. This is information only and not a recommendation to buy the product mentioned in this article.

Where is Old San Juan?

San Juan is the capital of Puerto Rico and located on the central north coast of the island. Old San Juan is the historic part of town, on a peninsula that juts out into the Caribbean Sea. Puerto Rico is an island between the Dominican Republic and The Virgin Islands and it’s about a 2 hour flight to the nearest spot of the mainland US.

How to get there

There are a lot of domestic flights into San Juan and a few international flights. Most major US cities on the east coast fly to San Juan. If your city doesn’t have a direct flight you’ll likely layover in Miami or elsewhere on the east coast. From the airport you can take a bus , taxi, Uber, or rental car to the Old Town, which is about 12km (7.5 miles) from the airport. 

If you’re combining a visit to Old San Juan with other destinations around Puerto Rico, it’s beneficial to have a car. You can use the search bar below to find a great deal on a rental in San Juan.

Parking in Old San Juan

If you’ve got your own wheels then I suggest parking in La Puntilla Parking lot . It’s right outside the old city walls and only $3 per day. It’s closed at night but there is free street parking at night nearby. It’s the perfect place to start your self guided walking tour of Old San Juan.

If you’re staying in the Old Town, though, your hotel might have parking included so be sure to check with your accommodation for parking options.

Puerto Rico speaks Spanish, but in Old San Juan just about everyone will be bilingual and speak English too. If you get outside of San Juan then you start running into places where the locals don’t speak English. 

Puerto Rican Food

Puerto Rico has its own unique cuisine. See the section below on Eat Like a Local.

Puerto Rico is part of the United States and uses the US dollar. Cards are accepted just about everywhere and it’s really not necessary to carry any cash, other than for parking lots and street vendors. San Juan is more expensive than you’d expect. It’s on par with smaller US cities in terms of the cost of everything.

You’d think with the GDP of Puerto Rico being lower than US states that things would be a bit cheaper but that’s not the case. It’s not as expensive as New York or Washington DC, but expect similar prices to midwestern cities.

Since you’re still in the US tipping is still a thing. You will be expected to tip at restaurants in San Juan.

Puerto Rico operates sort of like a state, but it’s not. It is a US territory instead, which means that US federal laws still apply, such as federal minimum wage and social security taxes, but citizens who live in Puerto Rico have no representation in the federal government.

They can join the army and go to war and die for the country, yet can’t vote for president. In 2020 Puerto Ricans voted by a slim majority to become a state, but it remains to be seen if that will ever happen.  

Weather in Old San Juan

Puerto Rico has a tropical climate and it’s hot and humid year-round. Summers are a bit hotter and rainier. San Juan is usually clear while the interior mountains are cloudy. You can reasonably expect San Juan to be hot, humid and sunny. 

You can also reasonably expect to get some rain if you’re there for more than a few days, so be sure to bring an umbrella with you on your trip.

Where to stay

There aren’t really any major hotel brands in Old San Juan. You’ll find a Sheraton on the south coast, but that’s really it. Old San Juan is full of small boutique hotels and holiday rentals instead, which adds to the charm.

They won’t be that much more expensive than staying outside the Old Town in one of the major brand hotels, but there are definitely more options and larger hotels outside. We stayed at Aloft San Juan but don’t recommend it due to loud music from the mall next door till well after midnight. 

Within the old town consider the 352 Guest House Hotel Boutique or the Casa Sol bed and Breakfast . Outside of the old town I like the Hyatt House or the Hyatt Place . They are right next to each other and It’s easy to get to the old town from there. Or check out all the listings on booking.com to find another great option!

Time of year to go

The peak tourist season runs from December to May. The weather is a bit cooler and drier. The summer months are the hottest and wettest but offer an experience with fewer tourists. The ideal time might be late spring to early summer. 

Just be mindful of when cruise ships stop in the port, because if you can avoid a cruise day that would be best. I explain how to avoid cruise days in a section below.

How long to stay in Old San Juan

It’s easy to see Old San Juan in one day. This self guided walking tour is structured around one day in the old town. A trip to San Juan should be combined with a beach vacation to Puerto Rico or a hike through the jungles of El Yunque National Forest, the only tropical rainforest in the US National Forest system.

Puerto Rico – “rich port” – was first settled in 1508 by the Spanish in a location outside San Juan’s city limits. A year later the settlement was moved to what is now San Juan and the name was officially added in 1521, which is the year the city is considered to be founded. Fortifications were built over the years and helped fend off numerous attacks, especially from the Dutch, French and English. 

For centuries it remained a small Spanish port city, never expanding beyond the original city walls. In 1898 the United States did what the Dutch never could and took Puerto Rico, thus ending the Spanish-American war. However, Puerto Rico did not become a territory until 19 years later. It has remained an American territory now for over 100 years. 

Over the years the colonial houses and buildings in Old San Juan degraded into a state of disarray. What you see today is the result of painstaking restoration of the old buildings that has taken place over the last 80 years. And they’ve done a hell of a job restoring the city to its original charm. These days Old San Juan is mainly a tourist destination. No more fending off invaders! 

If you’re curious what San Juan would have turned into had the Dutch taken over, then be sure to check out my complete guide to Amsterdam !

The Old Town is not large but there is a lot to see and do. Hitting all these spots will log 8-10 miles on your Fitbit. You can choose your own order of precedence, but hitting them in the order I have given below will make for happy feet. Check out the map below for the points of interest you’ll need to hit on this self guided walking tour of Old San Juan. 

The Colorful Streets 

Perhaps the main draw of Old San Juan is not one particular location, but the architecture of the city itself. The buildings are nearly all colonial-era Spanish architecture. The Caribbean has all sorts of old colonial-era cities, like the Zona Colonial in Santo Domingo or the Pietermaai district of Willemstad in Curaçao. But when it comes to colonial architecture, nothing beats San Juan.

This means cute balconies and colorful facades. All the streets are lined with charming houses of eclectic, bright colors. The old city itself is a UNESCO World Heritage Site. There is no single street to go for the best views. It depends on how many cars are parked and how crowded the city is. Rest assured there will be no shortage of photo ops on the streets of Old San Juan.

Castillo San Felipe del Moro 

Old San Juan’s most notable attraction is almost certainly Castillo San Felipe del Moro , the city’s original fort. This Spanish fortress was built over the centuries, starting in 1539. It’s an impressive structure and was used to fend off attacks, most notably from the Dutch in 1625.

These days the fort is part of San Juan National Historic Site, managed by the National Park Service. It was last used for military purposes during WW2 and since then has been solely a tourist site. It’s $10 per person to enter unless you have the NPS Interagency Pass or another yearly pass. 

The fort itself is an impressive structure. It rises seven stories from the water below and includes multiple fortifications and lookouts. It really reminded me of the beautiful ancient forts in Malta.

Allow at a bare minimum of an hour to visit the fort, but more if you want to walk along the coast along the promenade back to the Puerto de San Juan, the old city’s main entrance station. 

Castillo de San Cristóbal  

On the other side of Old San Juan lies another Spanish fort, Castillo de San Cristóbal . While not as well known, this fort is actually larger, the largest of its kind in the New World, i.e. the Western Hemisphere.

It was built about 100 years after San Felipe and meant to protect San Juan from land attacks. The two forts are connected by the old city wall that runs between them. 

Entrance to San Cristóbal is included with admission to San Felipe (and vice versa), so be sure to keep your receipt. It’s similar to San Felipe but has more viewpoints over land. This way the Puerto Ricans could see if the Dutch were gonna attack by landing somewhere else on the island and approaching on foot.

The two fortresses worked like a charm and Spain held on to Puerto Rico until it was surrendered to the United States in 1898. 

Catedral Basilica Menor de San Juan Bautista

The Catedral Basilica Menor de San Juan Bautista is the oldest church in the United States and the second oldest church in the Americas. While that might pale in comparison to some of the European gothic cathedrals, it’s still nearly 500 years old, dating back to 1540. I only admired it from the outside, but you’re free to walk in and have a look around. It’s not big and will only take a few minutes. 

Casa Blanca 

Casa Blanca is now a museum, but centuries ago this house belonged to famed Spanish explorer Ponce de Leon. It’s San Juan’s oldest house and contains many artifacts from the colonial days of the city. The house has some odd hours so consult the website linked above for the latest information. 

Puerta de San Juan 

Old San Juan’s original entry gate is found at Puerta de San Juan. It’s just an entryway in the city wall, but you can imagine old aristocrats arriving here hundreds of years ago. From here there is a lovely walk along the coast on the promenade. This takes you outside the city wall and eventually to the base of Castillo San Felipe de Moro. 

Situated outside the ancient city wall, La Perla is a former shantytown. Many years ago the slaves and lower class were forced to live outside the walls, thus La Perla was born. It’s full of colorful houses and right on the water, but you can tell the residents are not quite as rich as those inside the wall by one walk through the village.

It was also seriously damaged by hurricane Maria in 2017. Still cool to walk through though and your self guided walking tour of Old San Juan should definitely include a detour here. Just be careful at night, as there have been recent reports of violent crime aimed at tourists.

Musea de las Americas

If you’re into museums, or trying to beat the heat for a bit, pop into Musea de las Americas to learn a little bit about colonial life in Puerto Rico and see some artifacts from those days. 

Guided Tours

If you’d prefer to have a guide walk you around the city and add a bit of historic context onto your day in Old San Juan, then there are numerous short tours available with GetYourGuide , including walking tours as well as sunset cruises and sailing. You can even add on food tours, ziplining and all sorts of other adventurous activities. 

Make no mistake, Old San Juan can get pretty crowded. It’s not a huge area but it is an extremely popular place for American tourists. This is especially true on days when cruise ships dock at the port. The largest cruise ships can hold thousands of people. Now imagine all those people getting off at the same time and walking around Old San Juan.

If you’re not a part of one of these cruises then I highly recommend planning your trip to San Juan on a day where no cruise ships dock at the port. You can see which days have cruises using this link . About 500 cruise ships visit San Juan every year, and the vast majority visit between November and March.

In those months it’s very possible to have a day where three cruises stop at San Juan. And you absolutely do not want to be in town when three cruise ships are docked. So do yourself a favor and plan around the cruises. We were there on a summer day with no cruises and felt like we had the city to ourselves! 

For a small island, Puerto Rico has its own culinary culture. This isn’t intended to be a full rundown of Puerto Rican food but a quick synopsis on some of the main things to try. 

• Mofongo: the most Puerto Rican dish of them all. It’s essentially mashed fried  plantains served with some sort of meat. I’ve never seen it anywhere else in the world. It’s delicious. 
• Empanadas: Puerto Rican empanadas are fried and scrumptious. Don’t have too many though, as they are super unhealthy.
• Tostones and amarillos: deep fried green plantains and ripe plantains, respectively. 
• Arroz y habichuelas: red beans and white rice, served as a side with many meals. 
• Lechón asado: Puerto Rican succulent pig 
• Pastelon: Puerto Rican lasagna, made with plantains 
• Paella: this Spanish staple is found nearly everywhere in Puerto Rico 
• Flan: a vanilla custard cake. Simply amazing. 

Restaurants

There are tons of great restaurants in Old San Juan. Prices are in line with any large American city, and tipping is expected like anywhere else in the US. Most restaurants are indoors, as the narrow old streets don’t allow for much of a patio presence. You can find some rooftop bars and cafes though. 

To eat like a local, head to Cafe Manolin, a no frills ‘50s diner style restaurant with a huge menu. We had lunch there and dinner at Raices, which was recommended by the bartender at our hotel. It’s very popular and we waited over an hour for a table. But the stuffed avocado was excellent and worth the wait. The flan was also to die for. 

Some other restaurants that were recommended to us were Cayo Caribe, Cafe El Punto, and El Patio de Sam. Lastly, if you want to try the original pina colada, head over to Barrachina, where the drink was invented by bartender Ramon Portas Mingot in 1963. 

If you have longer in San Juan there are some more areas of the city that are worth checking out. Though I would say that I don’t recommend a beach vacation in San Juan city – even though there are plenty of beach resorts – due to the possibility of smoggy skies. It’s a big, dense city and you’re likely to get more beautiful skies further outside the city. 

Condado is the main beach area for San Juan. It’s lined with hotels and restaurants and worth a stop if you have a few days in San Juan. Pinky’s is a great spot for breakfast if you are in Condado.

In the Isla Grande region you will find a lot of new hotels (this is where we stayed) and a huge mall that has DJs every night in a common courtyard. Parque Isla Verde contains the airport and a long stretch of beach, as well as many 4 and 5-star hotels. 

The best beaches in Puerto Rico are well outside of San Juan. If you really want to see some amazing sand and water, take a day cruise to Icacos Beach on Cayo Icacos, a small island northwest of mainland Puerto Rico.

To get there you have to drive out of town quite a bit and take a boat to the island. There are tons of organized tours – like this one – so it’s not an issue getting there.

How long does it take to walk around Old San Juan?

Depending on your pace and how long you want to stop at the various sites, it could take anywhere from a few hours (no stops) to a few days if you stop to see everything. 

Do you need a tour guide for Old San Juan? 

No, you don’t need a tour guide for Old San Juan. This article explains how to do a self-guided walking tour of Old San Juan. If you want additional information on history and a knowledgeable local, having a tour guide can be beneficial though. 

Is one day in Old San Juan enough?

Yes, one day in Old San Juan is sufficient to see the highlights of the beautiful old city. 

Is it safe to walk around Old San Juan at night? 

Yes, it’s perfectly safe to walk around Old San Juan at night. It’s a happening place and there are people all over. Just see the next section about places to avoid. 

Where to avoid in Old San Juan?

After dark it’s best to avoid the La Perla neighborhood. Tourists have been known to get mugged and stabbed there in the wee hours of the morning. 

What is the difference between Old San Juan and San Juan? 

Old San Juan is a neighborhood of San Juan, a large city in Puerto Rico. “Old” comes from the fact that it was built in the Spanish colonial era. It’s the original San Juan. Since those days a sprawling metropolis has emerged from the old city, while the old city still retains all its colonial charm. 

Where do I park to access Old San Juan,

As discussed in the introduction, I suggest parking in the La Puntilla Parking lot when visiting Old San Juan. Cheap and right outside the city walls. 

Old San Juan is one of the most picturesque cities in the Americas. Walking the old cobblestone streets makes you think you’re in some historic European city. And if that wasn’t enough, the beautiful Spanish forts that protected the city for centuries really make you feel like you’ve landed in Europe. You’ll have a great time if you follow this Old San Juan self guided walking tour!

Chris Heckmann

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Old San Juan Walking Tour | One Day Puerto Rico Itinerary

Whether you’re visiting San Juan on a cruise or spending a few days in Puerto Rico, an Old San Juan walking tour should be at the top of your list of things to do!

As a former cruise ship worker , San Juan was one of my favorite ports to explore week after week.

One of the best decisions I ever made was taking myself on a self-guided walking tour of Viejo San Juan.

In just 3-4 hours, I was able to hit all of the major historical landmarks and popular photo-ops/ Instagram hotspots– and so can you!

Disclosure: This post contains affiliate links. By making a purchase through one of the links, I may receive a small commission at no extra cost to you. Thank you for your support and for helping me keep this blog up!

How to use this map: Click on the faded star next to the title to save this map, and click the square in the top left of the map before the title to view location details.

Self-Guided Walking Tour Suggested Routes

A self-guided tour through Old San Juan can be broken down into two main sections:

• The coastal perimeter (marked in black on the map)- Where most of the historical landmarks are located
• The interior streets (marked in burgundy on the map)- Where most of the photo spots, restaurants, and shops are found

If you want to hit all the locations listed on this free Old San Juan walking tour, I recommend breaking down your route into the two sections like I did and doing one after the other (in any order).

For those arriving from the cruise ship port, it may make more sense to walk around the exterior first and then end the day perusing the downtown streets.

I began this tour in the interior section as I took an Uber to Plaza Colon. After walking all the way down to the Umbrella Street, I then made my way clockwise to the listed destinations.

The Coastal Perimeter

Paseo de la princesa.

Paseo de la Princesa is a beautiful promenade lined with fountains, lamp posts, and trees— all accompanied with stunning views of the San Juan Bay.

On this picturesque boardwalk, you’ll find street vendors, art exhibits and shops, restaurants, bars, and even live music.

Address: 54 C. de la Fortaleza, San Juan

Where to stay in Old San Juan: Old San Juan Guest House , El Colonial Adults Only , Casa Sol Bed and Breakfast , Fortel Hostel

La Fortaleza

National Historic Landmark La Fortaleza (The Fortress) was built in the mid-1500s for military defense.

Since its establishment, it has served a number of purposes in addition to a fortress, including a prison, arsenal, and its current function as the governor’s residence.

Because the building is still an active government building, those interested in looking inside can only do so through official guided tours. These 30-minute tours are offered throughout the weekdays.

La Fortaleza can be seen from a distance while on the Paseo de La Princesa as well as at the end of the Umbrella Street (Calle Fortaleza).

Address: 63 C. de la Fortaleza, San Juan

Puerta de San Juan

Puerta de San Juan is the city’s iconic colorful gate that’s found at the northern end of Paseo de la Princesa.

It’s a historical landmark that was previously used to protect the city during colonial times. 

Standing 16 feet tall, the gate is also inscribed with the phrase, “ Benedictus Oui Venit In Nomine Domini ,” which means, “Welcome those who come in the name of God.”

Address: Cll Caleta De San Juan, San Juan

Museo de las Americas (Museum of the Americas)

The Museo de las Americas promotes the history and culture of the Americas through permanent and seasonal exhibits.

Visitors can learn about the indigenous, African, and European influences that shaped the Americas into the multi-faceted countries that they are today due to colonization and modern development.

The museum is actually inside what used to be the military’s barracks (Cuartel de Ballajá) during the colonial period. The beautiful courtyard is definitely a sight to take in!

You can also find unique, local folk art during the museum’s Domingo de Artesanos , which is an art showcase on the first Sunday of every month.

Address: Calle Beneficencia, San Juan

Website: museolasamericas.org

Hours: Thursday- Sunday 11 a.m.- 4 p.m.

Price: General Admission- $6; Under 12 and over 65 years old- $4

Need to rent a car while in Puerto Rico? Get a quote from Discover Cars here

Castillo San Felipe del Morro (“El Morro”)

Castillo San Felipe del Morro (also known as “El Morro” for short) is the island’s trademark fortification built at the tip of the San Juan Bay. 

Completed in 1790, the six-level fortress was strapped with a cannon, and together with another yet smaller fort, Fortín San Juan de la Cruz (“El Cañuelo”), the two structures produced a crossfire that would protect the bay’s entrance from intruders.

There’s so much to explore inside the fortress, from barracks and batteries to panoramic views of the bay.

El Morro’s presence domineers over everything in nearby site.

The vast green lawn that leads up to the fort’s entrance is the perfect location for a picnic, sunbathing session, or just a short break during your walking tour.

Although there are always groups of people hanging out, the area is so spread out that you’ll have no problem finding space for yourself away from others.

Tip: Keep your receipt! El Morro and Castillo San Cristóbal only require one entrance fee for both locations, so you’ll be able to get a 2-for-1 deal as long as your receipt shows that you’ve already paid for one ticket.

Address: Calle del Morro & Calle Norzagaray

Hours: Daily 9 a.m.- 6 p.m.

Price: General Admission- $7; Free for children under 15

Cementerio Santa Maria Magdalena de Pazzi

Just outside El Morro you’ll find the Santa María Magdalena de Pazzis Cemetery.

While it may seem strange that a cemetery is a landmark, the beautiful graveyard overlooking the Atlantic Ocean is definitely with a visit.

The cemetery’s location by the water was chosen as a way to symbolize a person’s spirit crossing over to the afterlife.

To this day, many of Puerto Rico’s most prominent citizens are laid to rest here.

If you don’t feel like going down and walking through the cemetery, it can easily be admired from the path leading to/from El Morro. 

Address: Calle Cementerio, San Juan

Cruising to San Juan? Book or plan your cruise with Cruise Critic — the industry’s top site for deck plans, cruise tips, ship details, and more!

Next to Cementario Santa Maria Magdalena de Pazzi and alongside the coast is La Perla, a historical shantytown.

The colorful neighborhood is most widely known recently as the filming location for the 2017 worldwide chart-topper “Despacito” by Puerto Rican artists Luis Fonsi and Daddy Yankee.

La Perla was first established as the location of a slaughterhouse as both slaughterhouses, cemeteries, and homes of former slaves and non-white servants were required to be outside of the main city center in the late 19th century.

Address: Calle Tiburcio Reyes + Calle Lucila Silva + Calle San Miguel + Calle Bajada Matadero

Castillo de San Cristóbal

Castillo de San Cristóbal is El Morro’s sister fortress that was build to protect the city from land attacks.

It’s the largest Spanish-built fortification built in the New World, spanning roughly 27 acres.

The fortress features several sentry boxes ( garitas) which are strategic lookout points that guards would use to keep an eye out for any potential threats.

Visitors can explore the different levels of the fortification as well as get a breathtaking panoramic view of Old San Juan and the bay.

Address: Calle Norzagaray & Route 25R (Avenida Luis Muñoz Rivera)

The Interior Streets

Plaza colón.

Plaza Colón is the land entrance to Old San Juan and can be recognized by its monument dedicated to Christopher Columbus.

The plaza is a good meeting or drop-off point if you’re taking a taxi or Uber to/from Viejo San Juan.

Address: C. de la Fortaleza & C. de O’Donnell

Insure your trip to San Juan with travel insurance. Get a quote with Insubuy here .

Plaza de Armas

Plaza de Armas is one of the city’s main plazas.

On the northern end lies San Juan City Hall, and on the west is the Department of State building.

At this plaza, you’ll find several statues, a fountain, benches, and street vendors selling local pastries and coffee.

Address: C. de San Francisco & Calle San José

Umbrella Street (Calle de la Fortaleza)

Perhaps one of the most Instagrammable locations in Old San Juan, Puerto Rico, Fortzaleza Street is home to the iconic and colorful hanging umbrellas.

The popular attraction is located at the end of Calle de la Fortaleza, just in front of La Fortaleza, where the governor resides.

It’s worth noting that the hanging decor changes periodically, so you might not always see vibrant umbrellas.

During one of my visits, the umbrellas were all camouflage patterned to represent the military.

In 2021, the umbrellas were replaced by a large banner with the Puerto Rican flag’s design.

Address: C. de Fortaleza, San Juan

Hotel El Convento

Hotel El Convento is a chic 4-star hotel with a rooftop pool that’s conveniently located in the middle of the city.

But more importantly, the few blocks around the area are absolutely gorgeous and worth checking out if you want some colorful pictures!

Address: 100 C. del Cristo, San Juan

Catedral Basilica Menor de San Juan Bautista

One block away from Hotel El Convento is the America’s second oldest cathedral, Catedral Basílica Metropolitana de San Juan Bautista, also known in English as the Metropolitan Cathedral Basilica of Saint John the Baptist.

Built in the mid 1500s, the cathedral is where the body of Ponce de Leon is entombed.

Address: 151 C. del Cristo, San Juan

La Puerta de la Bandera- Puerto Rican Flag Door

Any visitor will quickly see that Old San Juan is an oasis of art, from brightly painted buildings to beautiful murals on doors.

Another iconic photo spot in Puerto Rico is the Flag Door, or La Puerta de la Bandera from local artist Rosenda Álvarez.

Located at 51 Calle San José, a mural of the Puerto Rican flag is painted on the door of an abandoned historical building.

Address: 51 Calle San José, San Juan

Callejon de la Puerta Bandera- Flag Door Alley

Yet another popular Instagram photo location is also of the Puerto Rican flag on a door, but this time in an alley at the end of Calle Imperial.

I stumbled upon this mural without prior research as I was so immersed in the beautiful rainbow buildings in the neighboring streets.

If you have time (and enough energy), I definitely recommend spending a good half hour wandering through the area.

The streets are so colorful and perfect for photo ops.

You could even hire a Puerto Rico photographer for a fun and memorable photoshoot!

Address: Calle Imperial, San Juan

Where to Eat

A favorite restaurant among us cruise ship crew members is the Stuffed Avocado Shop .

While it’s not traditional or local eats by any means, it is the perfect option if you’re looking for a healthy meal with lots of fresh ingredients and greens– especially if you’re visiting San Juan on a cruise!

At this build-your-own-bowl eatery, patrons can choose from a wide and delicious selection of bases, protein, sauces, and toppings.

The menu also has a few “Signature Avocados,” with combinations already made for those unsure of what ingredients to put together.

From cauliflower rice and baby greens to pulled pork and mango tuna, the Stuffed Avocado is both tasty and healthy.

Address: 209 C. de San Francisco, San Juan

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Michelle is a freelance writer who has traveled to all seven continents and 60+ countries through various forms of employment. Over the last ten years, she’s worked as an ESL teacher in Japan, a youth counselor aboard cruise ships, and a hospitality manager in Antarctica.

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Self-Guided Walking Tour of Old San Juan - Puerto Rico Purple Guide

This Backpack and Snorkel Travel Guide (Puerto Rico Purple Guide) provides a self-guided walking tour of Old San Juan and ensures that you will be Making Memorable Moments on a relaxing vacation in Puerto Rico.

The information on this page and much more (google maps locations, more reviews, website links, etc.) is available in our Cruising the Caribbean Guide .

For Pinterest users, here are pins that you can use:

Plaza Colon 

Beautiful plaza in a trendy part of town with many restaurants and stores, and popular in the evenings.  The plaza is paved in marble and surrounds the statue of Christopher Columbus which was erected for the celebration of the fourth centennary of the Spanish rule in Puerto Rico.

Teatro Tapia 

South of the plaza is Teatro Alejandro Tapia y Rivera or short "Teatro Tapia" which is the oldest drama stage in San Juan.  It is named after the Puerto Rican poet and dramatist Alejandro Tapia y Rivera (1826-1882). It used to be the center of cultural life in San Juan for over one hundred years until it fell into neglect and was almost demolished.  It was restored in the late 1940s and again in 1976 and 1997 and now it shines in its old charm.  It is being used as a venue for musical theater, drama and other cultural events. 

La Casita de Rones 

Continue southwest until you get to La Casita de Rones, a flagship store of Rums of Puerto Rico which also houses two bars and a restaurant.  Stop by, relax, enjoy the water view, order a rum cocktail and have them some history with us about La Casita with you.

Paseo del Morro 

Now walk towards the water and make a right (north) on Paseo del Morro.  This path used to be a maintenance road for the city wall and is now a scenic and relaxing walk along the walls that once protected the city and a San Juan National Historic Site.  Consider coming here for a romantic sunset.

Aduana de San Juan (US Custom House) 

When you leave La Casita, look across the water to the southwest and enjoy a glimps of Aduana de San Juan, the US Custom House.   It is listed on the National Register of Historic Places and was established in the 18th century. The current building, however, was built in 1924 and the second story added in 1931.

Paseo de La Princesa 

Now walk to the northwest and pass the traffic curcle to get to Paseo de La Princesa. This street was named as “One of the Most Scenic Walkways in the World” and dates back to 1853.  It is a busy place for locals and visitors alike by day and night.  As you walk along the tree-lines street, you will see remains of the city wall which are part the San Juan National Historic Site.   On weekends you willf find live music, food stands, and crafts vendors.

La Princesa 

As you stroll along Paseo de La Princesa to the west, you will pass La Princesa, another one of many historic landmarks.  It used to be a prison in the past and now serves as the Puerto Rico Tourism Company’s headquarters.   La Princesa also houses the Puerto Rico art exhibit.

Self-Guided Walking Tour of Old San Juan ( see our Travel Guide )

The Old San Juan section of San Juan was declared a World Heritage Site by the United Nations in 1983 as the "San Juan National Historic Site".  It is beautifully restored and very walkable.  Visitors can either explore the city on foot or with the free tourist trolley  or by guided tour. Below is a free self-guided tour for you which brings you to the highlights of this beautiful city.  If you are looking for other things to see and do outside San Juan, then please check out my Puerto Rico Guide .

Start at Castillo San Cristobal 

Castillo de San Cristobal was completed in 1785 and is situated on 27 acres of land which makes it the largest fort in Puerto Rico.  It was built to protect Old San Juan against attacks from the east.  From here, the first shot of the Spanish-American War was fired in in 1898.  In 1942, oncrete pillboxes and an underground bunker control center were added by the US army. In 1961, the US army moved out and the US National Park Service took over the site.   In 1983, the "San Juan National Historic Site" encompassing the Old San Juan section of San Juan was declared a World Heritage Site by the United Nations.

Here are some more photos taken from various places inPuerto Rico

Are you interested in more white sand beaches and turquoise water destinations?

Check out my reviews of other Caribbean islands and Rudy's Cruise Guide .

Raices Fountain 

Keep walking to the west and you will come to the Raices Fountain which is considered to be one of the most romantic spots in Old San Juan.  Come here and/or Paseo del Morro to enjoy the sunset and sit on the terraced decks near the fountain. The Raíces Fountain was designed by architect Miguel Carlo to commemorate and celebrate the New World’s 500th anniversary and completed in May 1992. The bronze statues honor Puerto Rico’s mixed African, Spanish and Taino/Amerindian heritage.

Puerta de San Juan 

Puerta de San Juan was the main entrance to the city and one of five gates that allowed entrance into San Juan.

Plazuela La Rogativa 

Walk through Puerta de San Juan, turn left and up the steps to the "La Rogativa" bronze statue at Plazuela La Rogativa.  A Rogativa is a large procession of people that make a plea for help to God. The historic relevance is that British troops under Sir Abercrombie started a naval blockade of San Juan on April 30, 1797.  The desperate governor of San Juan ordered a “rogativa” and thus he and many women marched through the streets singing, praying and carrying torches.  Abercrombie believing that the sights and sounds were caused by reinforcements, thought that he would be outnumbered and retreated.

Escuela de Artes Plásticas y Diseño de Puerto Rico 

Follow the path up the hill until you reach the large grass area in front or the El Morro fort and then turn right to see beautiful yellow facade of the Escuela de Artes Plásticas y Diseño de Puerto Rico (=School of Plastic Arts and Design of Puerto Rico).

Castillo San Felipe del Morro - or short: El Morro 

Now walk across the grass area to what is likely going to be the highlight of your walking tour and, with more tha 2 million visitors each yea, the most popular historic site in all of Puerto Rico.  The El Morro fort. It was named in honor of King Philip II of Spain and was declared a World Heritage Site by the United Nations.  Itw as designed to guard the entrance to San Juan Bay. Construction started in 1539 and over the next 200 years, it was expanded and changed several times and it successfully averted several attacks.  Its last fight was in 1898 during the Spanish AMerican war in which Spain ceded ownership of Puerto Rico to the United States. El Morro's highest point is a lighthouse which reaches 180 feet (55 m) above sea level.  In 1961, the US army moved out an El Morro came under contro; of the US National Park Service. Wander through barracks, dungeons, passageways, and storerooms that El Morro has on six staggered levels and along its ramparts, where you can see multiple cannons, the domed garitas (sentry boxes) which have wonderful ocean views and which you have also seen at Castillo San Cristobal. 

Iglesia San Jose 

This church was constructed from 1532 to 1735 as part of the Saint Aquinas monastery and is the second oldest church in the Americas.  Puerto Rico's first governor, Juan Ponce de León, was buried in the crypt in 1559 but moved to the Cathedral of San Juan Bautista in 1836.  His coat of arms can still be seen near the altar.  A restoration project that was started in 2002 and is still ongoing revealed several painted murals including a mid-19th century depiction of the Battle of Lepanto.

San Juan Cathedral - Catedral Metropolitana Basílica de San Juan Bautista 

This Roman Catholic cathedral is one of the oldest buildings in San Juan, the oldest cathedral in the United States, and the second oldest cathedral in the Americas. The original building was constructed from wood in 1521.  After it was destroyed by a hurricane, it was rebuilt in 1540 and extended and modified several times over the next centuries.  The last remodel was in 1917. It contains the tomb of the Spanish explorer Juan Ponce de Leon and a shrine to the Blessed Carlos Manuel Rodríguez Santiago, the first Puerto Rican and Caribbean-born layperson in history to be beatified. The location of the cathedral was intentionally chosen.  As the cathedral is only a short walk away from the San Juan Gate, the first thing arriving sailors and travelers did was to walk from the gate to the cathedral to thank God for a safe voyage. Admission is free, but they ask for a donation.

That concludes the self-guided walking tour of Old Juan.

If you are interested in reading more about the best beaches, the US's only tropical rainforest, a bioluminescent bay, Bacardi manufacturing, and hotel reviews, then please check out my Puerto Rico Guide .

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Old San Juan Self-Guided Walking Tour: The Pearl of Puerto Rico

A perfect day: old san juan self-guided walking tour.

Old San Juan, the historical gem of Puerto Rico, is a vibrant showcase of colonial architecture, rich history, delectable cuisine, and a lively arts scene. This charming city is a must-visit on any trip to the Caribbean. Join us for an Old San Juan self-guided walking tour & see the very best of the city!

Why Old San Juan is an Unmissable Destination

Old San Juan is steeped in history and boasts a timeless beauty that transports you back to the days of Spanish rule. The city is characterized by its narrow cobblestone streets, vibrant facades, and impressive fortresses. You’ll also discover a thriving food scene, charming artisan shops, and a warm, welcoming culture that embodies the island’s spirit.

A Rich Tapestry of History

One of the oldest European-established cities in the Americas, Old San Juan is brimming with history. From the imposing fortresses of El Morro and La Fortaleza to the elegant architecture of colonial-era buildings, the city is a history buff’s paradise.

Vibrant Art and Culture

Old San Juan is a vibrant hub of Puerto Rican culture. Wander its charming streets and you’ll find an array of art galleries, museums, and independent boutiques selling locally made crafts. And of course, the city pulses with the rhythm of salsa, with music filling the air at night.

Embarking on Your Old San Juan Self-Guided Walking Tour

Walking is the best way to explore Old San Juan’s charms. With an easy-to-navigate grid layout, this city invites you to lose yourself in its vibrant streets and historic landmarks.

Must-Visit Sights

Start your tour at the Plaza de Armas, the city’s main square. Wander down Calle Cristo, passing iconic spots such as the San Juan Bautista Cathedral and the historic Hotel El Convento. From there, head to the imposing Castillo San Felipe del Morro, a 16th-century citadel offering breathtaking views over San Juan Bay.

Stroll along the Paseo de la Princesa promenade, lined with beautiful gardens, food vendors, and local artisans. Your walk will take you to the imposing gates of San Juan, the original main entry point to the walled city.

No self-guided walking tour would be complete without a visit to Calle Fortaleza, known for its vibrant umbrella-covered street and boutique shopping. Finish your tour at the colorful La Fortaleza Street, which leads to the governor’s mansion, offering a perfect photo opportunity.

Journeying to Old San Juan

Old San Juan is easily accessible from anywhere in Puerto Rico. If you’re staying in the capital, San Juan, it’s a short bus or taxi ride to the old city. For those coming from further afield, Luis Muñoz Marín International Airport is well-serviced by numerous international airlines. From there, it’s a short taxi or Uber ride to Old San Juan. Alternatively, many cruise lines dock in the city, making it an easy day trip.

Where to Stay in Old San Juan

Accommodations in Old San Juan range from charming boutique hotels in historic buildings to upscale resorts with stunning ocean views. For a truly unique experience, consider staying at Hotel El Convento, a former convent turned luxury hotel located in the heart of Old San Juan. No matter where you stay, you’ll be within walking distance of the city’s major attractions.

Prepare to immerse yourself in the historic charm and vibrant culture of Old San Juan. The city’s delightful mix of old-world beauty and modern Caribbean flair promises a memorable experience. Happy wandering!

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Best Things to do in Old San Juan, Puerto Rico: How to Go on a Self Guided Walking Tour

November 14, 2021 May 29, 2016 | Paroma

Last Updated on November 14, 2021 by Paroma

Looking to spend a few days in Puerto Rico and wondering what are the best things to do in Old San Juan? Then let this post answer all your burning questions on what to do in old San Juan with this fantastic self guided tour covering its best attractions! 

Disclaimer: This post may contain some affiliate links. Clicking on them may earn me a small commission at no extra cost to you for the product. Thank you for supporting free content on this site!

Table of Contents

WHY VISIT OLD SAN JUAN?

Puerto Rico , formerly a Spanish armed force and naval base, is an U.S. territory and a small island in the Atlantic Ocean, with tropical climate and beautiful, sun kissed beaches. Most people flock to this island to enjoy their time on the beach resorts in the newer Condado part of San Juan.

However for lovers of some old world charm will find solace in the beauty and vivacity of old town Puerto Rico which is a bridge and 10 min drive from the Condado/airport area. There are plenty of things to do in old San Juan during your Puerto Rico itinerary , which will mesmerize you with its beauty, colonial architecture, colorful houses and of course, a lot of history hanging on to its air like a musty cobweb. 

I have visited this city twice and have explored the old San Juan attractions simply by walking everywhere on its cobbled streets. So here is an account of my self-guided tour of old San Juan , which covers most of the sightseeing in old town if you have three days in hand.

This post includes tips on where to stay in San Juan, Puerto Rico, things to see in old San Juan, places to do some old San Juan shopping, and of course, tips on where to find some of the best restaurants in old San Juan.  

Best things to do in old San Juan

There are so many things to do in Old San Juan and the best way to explore them is by foot since the city is spread out like a grid and is thus very walkable. If you have semi-winged appendages, i.e. overly eager feet and are a  champion walker, you can explore the entire old town in two days.

If walking is really not your scene, take the free green trolley to the major attractions of old San Juan that have several stops all over town and the stops are clearly demarcated. Here are some of the top things to do when you are exploring old San Juan:

1) Admiring the colonial architecture

Old San Juan is indeed a beauty with her wares on full display, seeped in history starting from when Christopher Columbus first landed foot in 1492 to the modernities of today’s age reflected in the cafes, occasional fast food chains and other amenities jostling for space with the historic buildings.

The houses hark back to the Old Spanish colonial style, with dark wooden doors and windows that are slatted, beautiful pastel, neon and all other shades of colored walls and inner courtyards, very much in the Andalusian style. This website has a brief history of the Old San Juan architecture and its primary attractions and is a fun read for history aficionados.

Some of the best places to view colonial architecture in old San Juan are the following:

a) Calle de La Fortaleza: This is the artery of old San Juan and is flanked by beautiful, colorful homes on either side

b) The Casa Blanca (White house): this National Historic monument, built in  the 1520s for the Ponce de León, stands pristine on Calle San Sebastian and is home to a museum.

c) San Jose Church:  An excellent example of Spanish Gothic architecture, this beautiful church is located on Plaza de San Jose.

d) Palacio Rojo: This Baroque style building is on one end of Calle La Fortaleza and houses administrative offices

e) Palacio Episcopal: This continues to serve as the private residence of the Bishop of San Juan and is located on the Avenida de la Constitución.

2) Visiting the Spanish Forts

Old town boasts of the two Spanish fortresses Castillo Morro and Castillo Cristobal , two must visit World Heritage sites in San Juan that were built by the Spanish to protect this good port (i.e. Puerto Rico) from being invaded by other European forces (Dutch/French). These fortresses stand tall and proud on the north and east ends of the city and are must visits.

Castillo Cristobal was built in 1634 and was once considered the Gibraltar of the West Indies. This fort is one of the largest defenses ever built in the Americas and is currently a World Heritage and National Historic Site managed by the U.S. National Park Service.

Castillo Morro overlooks the San Juan Bay and is the labor of love of Spanish engineers over a period of 250 years (1539-1787). This was considered to be the grandest fortification built by the Spanish in the Caribbean.

Once atop the fort, you will get one of the best views in Puerto Rico of the old town shoreline along with a peek at the dotted white tombstones of the cemetery below. You can either walk along the guarded wall or adjacent paved way from one fort to the other or simply take the trolley.

3) Exploring Old San Juan museums

I) museo de americas.

San Juan is home to a few small, yet lovely museums hosting exhibits that you will not find elsewhere in USA, thanks to it being a territory and not a state. If you are a history buff, I strongly suggest visiting the Museo de Americas during your old San Juan walking tour which is one of the most beautifully curated museums that I have ever visited and one of the hidden gems of Old San Juan .

At a ridiculous entry free of $6, you get to see painstakingly detailed exhibits spanning the history, origins and anthropology of Puerto Rico, the folk art of the island, the information on the original Taino people who inhabited the island, the  arrival of the Europeans and finally the advent of the African slaves. All three races have influenced the island’s checkered and often turbulent history and left their mark on its cuisine, culture and music.

There is an entire section  of this old San Juan attraction devoted to the horrors of slavery as a part of Puerto Ricans to understand their African heritage, and this is something you will not see anywhere in mainland USA. So prepare yourself to encounter a very vivid narrative of a very dark past of the Americans, that includes a display of the torture devices to punish the runaway slaves.

Although I pride myself on having an iron stomach for most atrocities in man’s history, this was something very difficult to accept visually. Some of the exhibits on the lighter side were paintings on modern day symbolism and holograms of famous personalities, showing two sides of a coin.

ii) Museo de San Juan

I also peeked into the Museo de San Juan , another one of the many things to do in old San Juan, which is a free one and had only two galleries, one of which was devoted to the different translations of Don Quixote, the famous book written by the Castilian author Miguel De Cervantes and is the most translated book in the world after the Holy Bible.

I managed to take photos of the books translated in Indian languages such as Hindi and Bengali, but apart from that the exhibit had nothing much to offer unless you are a true blue linguist.

4) Walking down Paseo de la Princesa

Paseo de la Princesa should definitely be on your self guided tour of old San Juan . This is a beautiful promenade towards the harborside where you can go on a tranquil evening walk to catch the last rays of the sun glistening on the waters of the Atlantic.

You will see the Governor’s palace, a beautiful garden with a small fountain (called fountain of youth), ships passing by and a trail that leads to the Castillo Morro. The red San Justo gate stands tall and proud at the point where the trail starts and it is considered to be the entry way for Spanish Officials into the island starting from the 1500s.

At the center of this old San Juan point of interest stands a statue made of several figurines that depict the spirit of Puerto Rico, its people, its origins and its hopes and aspirations. A fountain caresses this statue which was unveiled to coincide with 500 years of Columbus’s arrival on this island.

There are several other statues found in the plaza (called Plaza of the Heritage of the Americas) nearby which were sculpted by Jose Buscaglia which represent the various sources of the heritage the Americas (Fuente de la Herencia de las Américas)-that of faith, blood, Hispanic heritage and Intellectual heritage. There is also a small garden with the statue of Elisa Rincón de Gautier where you can sit and relax.

5) Checking out Avenida de Constitución

Of all the things to do in Old San Juan , I really enjoyed my walk along the Avenida de Constitución that skirts along the Castillo Cristobal, where  the Capitol is located along with other administrative buildings. These were are anything but the staid, plain government buildings that we see elsewhere in USA. Brightly colored with ornate architecture, they too are very picturesque.

As you walk down this one way street, you will see 8 bronze statues of American President (including President Obama) on the pavement called Presidential walk. These are of the sitting presidents who have visited Puerto Rico while they held office.

The capitol is also open to visitors, but I was running low on time during my Puerto Rico itinerary and thus had to be content by clicking photos from the outside. In addition, there is the Puerto Rico police memorial as well as the holocaust memorial for the Jewish population inhabiting the island.

6) Souvenir shopping in old San Juan

Shopping in Old San Juan can be somewhat of a disappointment for those looking for local artisans and boutiques. Most of the old San Juan shops sell cheap souvenirs and trinkets, catering to the tourists and the remaining are the impersonal chains such as a Coach factory or Tommy Bahamas.

I still managed to find two amazing old San Juan stores in this sea of commercialization, who represented a slice of this town in their works and recommend them as places to shop in old San Juan . My favorite was Mi PeQueno San Juan (152 Calle Fortaleza) which is an artists shop selling replicas of real Old town doors, handmade from scratch.

These were mini versions of the beautiful andalusian architecture that you will find yourself surrounded by, during your old San Juan walking tour, and can be customized with your name. They were so beautiful that I simply had to buy one (see photo below).

The other store is called “Sea Foam Rare and Authentic” (101 Calle Fortaleza) and here I found the prettiest, nickel free copper earring etched with delicate patterns (see photo below).

7) Restaurants in old San Juan that you must visit

San Juan is having its moment of glory in the American Culinary scene and Old San Juan’s restaurants are a testimony to the creativity that is overtaking the island food. So if you are wondering where to eat in Old San Juan , you will be spoiled for options. Please stay away from all the tourist traps selling garbage and follow this foodie’s, aka my, trail for lip smacking food that fits all budgets. Here are some of my suggestions on where to eat in old San Juan :

i) Old San Juan street food: Start off with some fresh coconut water (straight out of a coconut) or Piragua (Puerto rican crushed ice with syrup) at one of the vendor stalls in the city squares

ii) Old San Juan restaurants: Have a quiet breakfast in the serenity of Patio del Nispero in Hotel El Convento , get hold of some amazing Latin-Asian fusion food at DragonFly , try some sumptuous mofongo (Puerto Rican mashed plantains stuffed with fillings, a food of African origin) at its sister establishment Aguaviva (right next door) or the amazing four/five or six course menu at Marmalade ( Best restaurant in San Juan , hands down and right across from my hotel and has a whole vegetarian section).

iii) Old San Juan Cafes: Don’t forget to get breakfast La Parisian style at Cafe Berlin (lots of vegan/vegetarian choices available including vegan mofongo), cold drinking chocolate and chocolate-hazelnut paste filled croissant at Chocobar Cortes chocolate bar and finally some Mallorca (sweet bread with powdered sugar) at one of the best places to eat in old San Juan , i.e. the famous La Bombonera cafe. 

Where to stay in Old San Juan, Puerto Rico

I strongly recommend Hotel Casablanca , a Moroccan themed hotel on Calle Fortaleza, in the heart of the city where I stayed during my second visit and loved the convenience and service!

Seriously, If you are looking for a budget boutique hotel in the heart of old town, Casablanca is possibly one of the best hotels in San Juan. Unlike what it says on the website, the hotel now has a functioning elevator so you don’t have to huff and puff up the stairs with your luggage in tow.

The hotel is very vintage, very quirky in its choice of wall paintings (eclectic, pop-art kind of) and has delicate Moroccan touches such as lamps and chandeliers. The rooms are very modest with a bed, two side tables and separate washrooms for bathing and doing your business.

There is also a flowing mosquito net that hangs from the top and  lends a touch of bygone-era class to the otherwise spartan decor. The funniest thing that caught my eye at that time was the continuous playing of the famous movie “Casablanca” on loop on the hotel lobby monitors.

The rooftop offers a good view of the city and is free to all guests. The room rates are surprisingly on the cheaper side (less than $130/night) for the location and popularity of the hotel. The front desk is active 24/7 and you can request them for any reasonable amenities.

Finally, there is free WIFI which you cannot beat! Again, I HIGHLY RECOMMEND this charming, quaint hotel in the heart of Old Town in lieu of the monstrosity of the resorts in the Condado area that you’ll encounter during your San Juan, Puerto Rico vacation . It’s centralized location is a big plus for your self guided tour of old San Juan.

Best time to visit Old San Juan

Puerto Rico enjoys tropical (read hot and humid) climate year round, so suffice to say skip summer (which is also rainy season). Winter is peak tourist season, but mid April-June is the perfect time to visit (warm weather than won’t make you feel like you’re in a humid oven and not too many tourists). I have been to Old San Juan twice in May and loved the sunny days and warm nights

This in a nutshell, was my take on things to do in old San Juan , a city I revisited this year and the one I love coming back to. I hope you get to visit it someday too in your travels and enjoy its offerings and beauty as much as I have. Do share your travel experiences with me and let me know if you found my tips helpful. As promised, click below to download your free PDF itinerary.

DOWNLOAD THIS FREE OLD SAN JUAN ITINERARY NOW!

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10 thoughts on “Best Things to do in Old San Juan, Puerto Rico: How to Go on a Self Guided Walking Tour”

I’ve been to Puerto Rico several times, but have not made it to Old San Juan yet! I just love historic cities like this! We have been to Rincon several times…..you have to visit if you ever get a chance!

Great list! I’ve twice had all-day layovers in San Juan (en route to St Croix) and have wandered around Old Town both times – I love how colorful the buildings are!

Absolutely love this post as it reminded me of my time in San Juan. I love your photos and this is very detailed information.

And like you, definitely not one to stay in the beach throughout my holiday. I’ll get bored out of my mind and my adventurous side will be screaming for an escape. I do love some time by the beach towards the end of my trip though. Just so I can end it on a relaxing note.

Great post, thanks for sharing.

Very informative post on Puerto Rico. I plan on going there soon. I’ll be saving your post. BTW is that rooster real?

Stunning pictures and seems you have got yourself throughly acquainted with this “pint-sized” city ?

I was in San Juan about a year ago, and you have perfectly captured the city! I’d love to get back. It’s safe, friendly, and historic. Great job!

These photos are so stunning! I’ve never been to San Juan, but I would absolutely love to go! Will definitely keep your recommendations in mind if I ever make it over there!

More than anything else, your vivid description and stunning photos makes me want to jump from where I am right into the photos! Very nice captures! Keep up.

Wow your photos are stunning, such a detailed post too. Puerto Rico is on my bucket list for sure.

Literally a rainbow on earth Old San Juan! I just love how authentic the street art looks too!

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Old San Juan Tour : Self-Guided Walk

Tour Details

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Welcome to the old san juan tour.

Embark on a walking tour of San Juan, full of majestic architecture, breathtaking views, and embattled history. Behold the largest Spanish-built fortification in the Americas. Hear stories of pirate battles, greed, and power, featuring figures like Sir Francis Drake. Stroll down ancient city streets rich with culture and history, then walk along this beautiful city’s old walls and enjoy some gentle ocean views.

About the Tour

Your self-guided walking tour begins at the Cruise ship pier, which features a painted beating red heart! Next, stop by the Teatro Alejandro Tapia y Rivera, one of the oldest drama theaters in the US, and which is also supposedly haunted!

Then you’ll come to the Plaza Colon, with its towering statue of Columbus. Hear how Columbus claimed the island and how San Juan got its name! As you stroll along these scenic streets, take in the majestic Castillo San Cristobal. You’ll unearth the story behind its construction and hear about the vast riches that brought so many explorers to this island.

Up next is the colorful and historic La Perla neighborhood by the seaside. You might recognize it as the music video filming location for the hit song “Despacito!” Then get to know Sir Francis Drake and revisit his fight to seize the island from Spain. Learn how his Spanish adversary, General Sancho pulled off a victory even though they were hugely outnumbered! You’ll also hear about the Second Battle of San Juan and find out why it was such a short-lived win for the English.

Your historical journey takes even more twists and turns as you uncover subsequent Dutch efforts to take power. Learn how they torched the city and how the Spanish fought to prevent this defeat from repeating! As you keep walking, you’ll behold ancient walls and gunpowder magazines, then finally the awe-inspiring Castillo San Felipe del Morro itself! And speaking of attacks, hear about Puerto Rico’s struggles for independence and find out why the US got involved.

Hear how the fall of El Morro marked a major turning point in world history.  Also be sure to take in the breathtaking ocean views and give yourself a little respite! Pay a visit to the Cuartel de Ballaja, which now houses the Museum of the Americas,

Then continue onto the Casa Blanca. Hear how it was meant for Ponce De Leon, and learn the story of the grandson who wrote one of Puerto Rico’s most critical historical texts! Also find out how Ponce De Leon himself met a poisonous end! The next stop is the historic Catedral Basilica Menor de San Juan Batista, the final resting place of Ponce De Leon.

Learn how the oldest church in the Americas survived countless attacks over the centuries, including Dutch attacks and Hurricane Maria. As the journey winds down, stroll along lovely cobblestone streets to the Puerta San Juan, the only remaining gate from the old city. 

Your tour concludes just past the famous La Fortaleza, a towering fortress dating back to the 1530s!

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Where To Start?

We recommend Starting From: Cruise Ship Pier, FV7Q+H8W, San Juan, 00916, Puerto Rico

How Does It Work?

• Once you book a tour, you’ll get a text/email with instructions.
• Download the app (while in good wifi/signal) and use your unique password to access your tours. If there are multiple versions or entrances for your tour, be sure to download all audio guides.
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• Please note that no one will meet you at the starting point.

Preview The Tour

  what is the starting point of the old san juan walking tour.

The tour begins at the colorful La Corazon Steps, featuring a painted beating red heart.

  What is the significance of the Teatro Alejandro Tapia y Rivera on the tour?

The Teatro Alejandro Tapia y Rivera is one of the oldest drama theaters in the US and is rumored to be haunted.

  What can you see at Plaza Colon, and what historical event is associated with it?

Plaza Colon features a towering statue of Columbus, and you can learn about Columbus’s claim to the island and the origin of San Juan’s name.

  What historic site is encountered during the tour that played a role in the island’s defense?

The majestic Castillo San Cristobal is encountered, and you can discover its construction history and its connection to explorers seeking riches on the island.

  What is the significance of the La Perla neighborhood on the tour?

La Perla is known as the filming location for the music video of the hit song “Despacito.”

  Who was Sir Francis Drake, and what role did he play in the history of San Juan?

The tour covers the story of Sir Francis Drake and his attempt to seize the island from Spain, as well as the Spanish General Sancho’s defense.

  What historical events involving Dutch efforts are explored during the tour?

The tour delves into Dutch attempts to take power, including the torching of the city, and the Spanish efforts to prevent further defeat.

  What is the significance of Castillo San Felipe del Morro on the tour?

The tour visits Castillo San Felipe del Morro, and you can learn about its historical importance, including attacks and defenses.

  Why is the fall of El Morro considered a significant event in world history?

The tour explains how the fall of El Morro marked a major turning point in world history.

  What is the final stop on the tour, and what is its historical significance?

The tour concludes just past the famous La Fortaleza, a towering fortress dating back to the 1530s, which played a crucial role in the island’s history.

Inclusions and Exclusions

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Self Guided Tour San Juan Puerto Rico: Exploring The Heart of The Caribbean on Your Own

Key takeaways – self guided tour san juan puerto rico, takeaway 1: explore the rich history and architecture of old san juan.

Embark on a self-guided walking tour through Old San Juan and immerse yourself in the beauty of historical buildings and architectural monuments. Get your hands on a walk route map online and discover well-known sights like the Coastal Perimeter, Paseo de la Princesa, La Fortaleza, and Puerta de San Juan. Don’t miss out on visiting museums such as Museo de las Americas or Aduana de San Juan to delve deeper into Puerto Rican history and culture. And of course, make sure to explore the impressive fortifications of Castillo San Cristobal and El Morro. These sites offer amazing insights into the city’s fascinating past. Oh, and don’t forget to stop by the Old City Gate – it’s a must-see!

Takeaway 2: Immerse yourself in local life

If you want to experience the local way of life, be sure to visit vibrant squares like Plaza Colon or take a leisurely stroll down blue cobblestone streets. And if you’re craving some natural beauty, head over to Paseo del Morro for breathtaking ocean views. Looking for refreshments along your tour? Drop by La Casita de Rones for a taste of local rum. And if you’re interested in picking up some unique crafts, check out the various markets where artisans sell their works throughout the city.

Takeaway 3: Enhance your exploration with audio tours and outdoor activities

For those who prefer an auditory experience, consider getting self-guided audio tours narrated by local experts. These tours provide detailed information about each location you visit during your walk – it’s like having your own personal guide! But if you’re looking for more than just walking, there are plenty of companies that offer equipment rentals for activities like paddleboarding at Condado Lagoon or kayaking. And if you’re up for a day trip outside of San Juan, guided audio tours can take you to places like the enchanting El Yunque rainforest. Just remember to wear comfortable shoes, bring water, and be ready for a few hours of walking. Take your time to pause and enjoy the lovely parks and gardens scattered throughout the city – they’re worth it!

Table of Contents

Here’s a Youtube Video about Self guided tour San Juan Puerto Rico

Welcome to your ultimate guide to planning a self guided tour of San Juan, Puerto Rico . This Caribbean gem has a wealth of history waiting to be discovered in Old San Juan , as well as an array of local culture that can be explored in its museums and vibrant squares. Nature lovers will find plenty of scenic spots and natural wonders, while food enthusiasts can indulge in local flavors, rum and artisan crafts.

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Planning Your Self-Guided Tour of San Juan: What You Need to Know

Welcome, fellow travelers! Let’s embark on an unforgettable journey through the vibrant streets of Puerto Rico’s capital city, San Juan. If you’re planning a self-guided tour , I’m here to help. By the way, I have a hint for you – keep your eyes open for a San Juan walking tour map online that will guide your exploration.

You see, this beautiful city offers an array of self-led walking tours that let you explore San Juan on your own . As someone who has experienced the wonders of this place first-hand, I’d highly recommend it. Just ensure you wear comfortable shoes and carry water as you’ll be doing quite some walking!

Discovering the Historical Wonders of Old San Juan

A stroll through Old San Juan , one of the most popular routes for all our visitors, reveals stunning historical buildings and architectural monuments. Every step taken through Old San Juan unravels snippets from Puerto Rico’s past; each corner telling its own fascinating tale.

In any case, don’t miss out on well-known sights such as La Fortaleza and Puerta de San Juan or even the majestic fortifications like Castillo San Cristobal and El Morro – all top sights in Puerto Rico’s capital city. All things considered, these are significant landmarks that reflect the tumultuous past and resilience of this Boricua city.

Uncovering Local Culture at Museums and Vibrant Squares

The cultural immersion doesn’t end with architecture alone! On your Solo travel in Puerto Rico’s San Juan, visit key museums like Museo de las Americas or Aduana de San Juan to delve deeper into Boricua history and culture.

Afterwards, relax in the vibrant squares such as Plaza Colon and watch local life unfold before your eyes. During this pause, take in the scenery of blue cobblestone streets that give the city its distinctive charm.

Exploring the Natural Wonders and Scenic Spots of San Juan

Now that I think about it, one of my favorite parts about my self-guided tour in San Juan, Puerto Rico , was soaking up nature’s beauty. Imagine strolling down picturesque paths like Paseo del Morro with scenic ocean views at every turn.

In any case, during your tour don’t forget to visit places like the Old City Gate – this historical monument is a must-see spot in Puerto Rico’s capital city.

Food, Rum, and Crafts: The Best Places to Experience Local Flavors and Artistry

An exploration is incomplete without indulging in delicious local food! On these walks through San Juan tourist attractions, , la Casita de Rones is an ideal pit stop. Here you can sample their exquisite rum – a renowned specialty of Puerto Rico – a real treat for rum aficionados!

Besides food and drinks, you can explore markets scattered throughout San Juan where local artisans display their creativity. It’s truly one of the best ways to support local businesses during your journey.

Enhancing Your Tour with Self-Guided Audio Experiences

If you’re wondering how to enrich your travel experience while venturing through San Juan’s streets – consider acquiring self-guided audio tours available online! These are narrated by local experts providing background and detailed insights into each location you visit.

Venturing Beyond the City: Equipment Rentals for Independent Activities

For those seeking more than just a walking tour, you’re in luck! From paddleboarding at Condado Lagoon to renting kayaks, there are several companies offering equipment rentals for independent activities. And if you wish to venture further afield from San Juan, guided audio tours are also available including trips to places like El Yunque rainforest.

All things considered, a San Juan self-led tour is an interactive way of experiencing this vibrant city at your own pace. Not only does it offer insight into the local culture and history, but also allows ample opportunities to soak up natural beauty, sample local cuisine and support local crafts.

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Embarking on a self-guided tour in San Juan, Puerto Rico can be an exhilarating experience, especially when you have the perfect insider tips and guidance. While planning your visit, you may want to consider how many days you need to see Puerto Rico . In this context, check out How Many Days To See Puerto Rico post which provides useful insights and would help enhance your tour planning process. To make your stay comfier, it’s essential to figure out the best places that would cater to all your needs. The post on Best Hotels in Puerto Rico for Families is an excellent resource for finding family-friendly accommodations around the island. This could significantly boost the quality of your self-guided journey. Speaking of quality experiences during tours, you certainly wouldn’t want to miss out on exploring some iconic sites such as the famous black sand beaches. A quick look at our post about a Black Sand Beach Puerto Rico Tour will give you splendid ideas for beach destinations that can add color and excitement to your itinerary. Lastly, every tour in San Juan becomes more memorable with a taste of local flavors. Sample some authentic beverages by referring to our list of popular Puerto Rican drinks . Packed with recommendations and valuable information about these delicious drinks, reading Popular Puerto Rico Drinks will undoubtedly enhance your self-guided tour gastronomically.

My Personal Take about Self guided tour San Juan Puerto Rico

Hi there, friend! It’s your buddy Steve , the so-called “guru” of everything travel in Puerto Rico.

Quite flattering – but on to more pressing matters. Ever thought about taking a super cool self-guided tour San Juan, Puerto Rico ?

Yeah, that really sits well with you right?

You see, there’s nothing quite like the feeling of exploring Puerto Rico’s enchanting capital all by yourself, at your own pace! Embrace the vibrancy and rich heritage with every step you take through its winding historic cobblestones streets. Now that I think about it… just envision stopping over a vibrant street café for authentic Criollo cuisine or perhaps meandering down distinct blue-stoned paths in Old San Juan – so much beauty in one place! But remember my words of advice, planning is key.

• Create your itinerary carefully.
• Schedule time for unexpected discoveries because believe me, those happen a lot here.

In any case, if architecture and history thrusts your adrenaline like it does mine – dipping into majestic forts like El Morro or La Fortaleza should pique your interest. By day experience these marvelous relics from colonial eras past and by night immerse yourself in electrifying nightlife! You see my friend, ‘The Heart of The Caribbean’ kkeeps drumming an irresistible beat drawing globetrotters from every corner around her turquoise shores Rosy-pink sunsets mirroring off pastel-colored façade…aaah sweet San Juan,

She awaits to spin her magic.

Take heart from these thoughts and dare to transform it into colorful reality. Because, you see, paradise isn’t a distant utopia – it could be just a self-guided tour San Juan Puerto Rico away. Come explore Puerto Rico and let her soulful rhythm capture your heart. Plans are only good intentions until they immediately become an adventure. From my heart to yours – make something magical tomorrow!

You won’t regret it in the slightest.

As always feel free to reach out with your questions about travel to the great frontier of our world that’s Puerto Rico or any chunks of advice you might offer other curious souls!

Aquí te espero. – Here I await you.’ Cheers! -Steve-

          View this post on Instagram                       A post shared by Grillers Puerto Rico (@grillerspr)

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Frequently Asked Questions about Self guided tour San Juan Puerto Rico

1. what are some popular attractions to explore during a self-guided tour of san juan.

Popular attractions in San Juan include the Coastal Perimeter, Paseo de la Princesa, La Fortaleza, Puerta de San Juan, Castillo San Cristobal, El Morro, and the Old City Gate.

2. Are there any museums worth visiting during a self-guided tour of San Juan?

Absolutely! The Museo de las Americas and Aduana de San Juan offer fascinating insights into Puerto Rican history and culture.

3. Where can I indulge in a local rum tasting experience during my tour?

You should definitely make a stop at La Casita de Rones for an authentic local rum tasting experience.

4. Can I explore natural beauty spots during my self-guided tour of San Juan?

Absolutely! Don’t miss out on scenic ocean views at Paseo del Morro or exploring vibrant squares like Plaza Colon. You can also stroll down blue cobblestone streets for an immersive experience.

5. Are there any options for audio-guided tours available online?

Absolutely! You can enhance your exploration by acquiring self-guided audio tours narrated by local experts online. These audio tours provide detailed information about each location you visit during your walk.

6. Can I engage in independent activities outside of walking around Old San Juan?

If you’re looking for more than just walking around Old San Juan, there are companies that offer equipment rentals for activities such as paddleboarding at Condado Lagoon or kayak rental. You may also consider guided audio tours that take you to places like the El Yunque rainforest if you wish to explore other parts of Puerto Rico outside of San Juan.

Now you know Self guided tour San Juan Puerto Rico , but that’s only the beginning of your journey here at we like PR. If you found this post useful there’s more to learn to get you to the next step of your Puerto Rico journey. If you read our next articles you’ll be a step further than most people.

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The Ultimate Self-Guided Walking Tour of Old San Juan

If you’re traveling to San Juan, you have to visit the historical district of the city, Old San Juan. And if you’re traveling on a budget or just want to do your own thing, you should use my self-guided walking tour! This all-in-one walking tour will hit all of the historical AND Instagram-worthy spots. Let’s get started.

This tour is about 5 miles in total when you include walking around all of the forts. It took us about 8 hours to complete it comfortably. If that sounds like too much for you, check out the short version of this tour here .

There are two ways to use this tour: You can use the included maps and Google links to navigate from stop to stop, or you can simply type each stop into your phone’s maps one at a time.

Start your day by 9am in order to finish everything on the tour during operating hours.

The entire tour is free with the exception of the two forts. Entry costs $10, which gets you into both forts for the day. Alternatively, they are national parks, and an annual national parks pass will get you in for free. I loved visiting the forts, especially San Cristobal. I recommend paying for entry.

Warning: The sun in Old San Juan, like most of the island, is brutal! It’s especially bad in this area because you are surrounded by concrete and very little shade. Bring plenty of water, sunscreen, a large hat, and sunglasses. You’ll thank me later!

• Cafetería Mallorca
• Plaza Colon
• Castillo San Cristobal
• Paseo de la Princesa
• San Juan Gate and City Wall
• La Fortaleza
• Calle de la Fortaleza
• Plaza de Armas
• Cathedral of San Juan Bautista
• El convento hotel
• Caleta de las monjas
• PR Flag door
• Museum of the Americas

1. Cafetería Mallorca

Our first stop is for breakfast at Cafetería Mallorca! Make sure to get here by around 9am and leave by 10am in order to stay on schedule for the day. This place is incredible and a must-do while in San Juan! As the name suggests, they sell Mallorcas, which are traditional Puerto Rican breakfast pastries. They are absolutely delicious, and the two of us ate for around $10 total. You can’t beat it.

I highly recommend the Mallorca with bacon and Swiss cheese (make sure to say the cheese type or else you’ll get American cheese). I also recommend sitting at the bar, which is much faster. This place is popular , especially on the weekend. Sitting at the bar allows you to skip the long line for table service, and you’ll feel like you’re getting a more authentic experience at this mom and pop restaurant. If there is a line out the door when you arrive, don’t be afraid to wait. It moves very fast, and it’s worth it.

2. Plaza Colon

Our next stop will be Plaza Colon. This plaza is on the way to Castillo de San Cristobal, and you can check out the Christopher Columbus statue in the center.

3. Castillo San Cristobal

This was one of my favorite stops on the entire tour. It costs $10 to enter, but this ticket will also provide entry to the last stop on this tour, El Morro. Alternatively, you can get in for free with a National Parks Pass. The fort is open daily from 9:30am-4:30pm. To get there from Plaza Colon, look for a hill and follow the sign that says “Enter through historic ramp.” Out of all the stops, we spent the most time here. The history is interesting, and the views are gorgeous!

Pro tip: When you’re approaching the entrance to the fort, look to your left. You’ll see a grassy area and a lone garita (sentry box). Head down there for some killer views of the fort!

Puerto Rico has historically been the gate to the Caribbean. Not only did the Tradewinds and ocean currents funnel European ships to Puerto Rico, it also was the first island they encountered with a bay deep enough for a port. This was the perfect place for the Spanish to defend all of their riches in the Americas. Castillo San Cristobal was the second fort built on the island, primarily for defense against land attacks.

As Spain began to lose control over its colonies, maintaining control over Puerto Rico became less important to them, and the forts slowly slipped into disarray. In 1898, the conditions were perfect for the U.S. to conquer the Spanish territory.

The U.S. once again put the fort to use for defense during WWII, which was the last time it was actively used for military purposes. It has been a part of the National Parks Service since 1961.

*Information curated from various informational exhibits in the fort

4. Paseo de la Princesa

Walk down Calle de la Fortaleza on your way to Paseo de la Princesa. This is a great opportunity for window shopping at the boutiques. When you get to Paseo de la Princesa, enjoy strolling down San Juan’s main promenade. We also got a lovely handmade Christmas Ornament from the shops set up along the street!

5. San Juan Gate and City Wall

Next, we will walk along the city wall to la puerta de San Juan (San Juan city gate). Make sure to use the above map for directions. You can take a beautiful path by the water that connects Paseo de la Princesa and the gate, but Google maps will try to take you through the city. You don’t want to miss this beautiful stretch!

The defensive city wall is 20 feet thick! As you pass through the gate, take a moment to notice the thickness of these massive walls. On the other side, you’ll find a street vendor selling piragua. Piragua is basically a snowcone, but it’s a local favorite and a great way to cool off at this point of the tour!

6. La Fortaleza

Once you pass through the gate, you’ll find La Fortaleza down the street to your right. This mansion is the home of the governor of Puerto Rico. When we went, the street was blocked off by security, but if you can get close, take a look at this beautiful home! It’s the oldest executive mansion in the Americas.

7. Calle de la Fortaleza

We took a quick stroll down Calle de la Fortaleza earlier on our way to Paseo de la Princesa, but now we are going to see why it got its other name: the umbrella street! Several years ago, just outside of La Fortaleza, umbrellas were hung over the street. It was so beautiful and popular that it became a permanent exhibit. The umbrellas are periodically changed out, and when we were there, they had strung up rows of fairy wings!

8. Plaza de Armas

La plaza de armas is the central square of San Juan and a great place to rest during the heat of the day. You can sit by the beautiful fountain, shop at one of the local vendors, or grab a coffee in what looks like a secret garden.

9. Cathedral of San Juan Bautista

This is the second oldest cathedral in the Americas, and the home of the first school in Puerto Rico. It is free to enter and open daily from 8am-4pm. Inside, you’ll find the tomb of the Spanish explorer Juan Ponce de León.

10. Caleta de las monjas

The next three spots are included primarily for helping you get the most beautiful San Juan backdrops in your instagram photos. If you’re not interested in that sort of thing, feel free to skip ahead to stop 13, the Museum of the Americas.

Caleta de las monjas is the quintessential San Juan street. Here you’ll find the most brightly colored and well maintained street fronts for your social media needs. It’s also not very crowded, so you won’t have mobs of tourists in the background.

11. El Convento Hotel

This hotel is gorgeous, and you don’t have to stay there to go inside and take some gorgeous photos! They also have a restaurant if you want to eat amongst this beautiful view.

12. PR Flag Door

Located at 51 Calle San José, you’ll find the Puerto Rican flag door street art, a symbol of Puerto Rican independence.

13. Museum of the Americas

The Museum of the Americas is a great place to learn about the history and culture of the American continent, with a particular focus on Puerto Rico. The hours vary depending on the day of the week, so check in advance before you go. Entry is $6. Most of the exhibits are in Spanish, but you can purchase an audioguide in English.

You will almost certainly not have time to enter this museum during this walking tour, but it’s a good place to go back and visit! If you don’t want to go inside, you’ll just pass by on our way to our final destination:

14. El Morro

Starting from the Museum of the Americas, it’s pretty much impossible to miss the giant road leading out to el Morro, the first fort built on Puerto Rico. You’ll probably see locals flying kites and picnicking in the massive lawns leading up to the fort. At this point, you should fish out the ticket you bought at Castillo San Cristobal. Either that ticket or your national parks pass will get you into El Morro. It’s open from 9:30am-4:30pm each day, which should not be a problem if you started the tour on time and kept a decent pace.

El Morro shares much of the same history with Castillo San Cristobal, being built by the Spanish to protect their exploited riches and then used for defense by the U.S. during WWII. This fort, however, was primarily designed for water attacks. It’s composed of 6 levels, aka lots of stairs!

It may have been the heat exhaustion and blistered feet, but I preferred San Cristobal over El Morro, despite El Morro being the better known option. If you only have the time or walking stamina for one, I’d recommend San Cristobal. There were cool underground tunnels and just as many scenic ocean views!

Alternate route: If you don’t have any interest in entering El Morro, circle back to la Puerta de San Juan. Then follow the coastal path called Paseo del Morro all the way to the back of the fort. You’ll enjoy the ocean scenery the entire way and appreciate the imposing face of El Morro which would have greeted every enemy ship.

After all that walking, kick up your feet and grab a delicious dinner in Old San Juan. The perfect ending to a perfect day.

Tag me in your stellar Instagram photos, and let me know what your favorite part of the tour was in the comments below!

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Walking Around Old San Juan – A Self-Guided Tour

Walking Around Old San Juan - Why Visit Old San Juan, Puerto Rico

Before I get into my experience walking around Old San Juan, Puerto Rico, I would like to provide a brief history of this popular tourist area.

Old San Juan is the historical portion of San Juan, which originates as early as 1508. The city was originally walled in, but in 1897 the wall was demolished. This demolition led to a huge expansion of Old San Juan.

By 1940, many of the buildings were in bad shape and in need of repair. Over the years, the Government of Puerto Rico and many local banks have assisted in remodeling most of the buildings. Today, Old San Juan features beautiful colorful buildings, blue cobblestone streets, and many sculptures and fountains.

Be sure to look at a map prior to your walking tour of Old San Juan. Since the city was originally walled in, most of the roads are too narrow for two cars to pass through. Because of this, most of the streets are one-way, with some being pedestrian-only.

Author’s Note – During my visit to Puerto Rico, I had not yet decided to create this website.  My trip was geared towards relaxing more than researching and learning about the history, culture, and geography of Puerto Rico.  I hope to return to Puerto Rico in the future and update this page.

Walking Around Old San Juan - Table of Contents

Updated – Feb 16, 2022

• Why Visit Old San Juan

My Experience Walking Around Old San Juan

Old san juan tours and packages.

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I began my self-guided walking tour of Old San Juan at the El Morro Fort. After an early morning visit to El Morro, I decided to head over to the San Cristobal Fort. Since the route took me directly through the heart of Old San Juan, it was the perfect opportunity to spend a few hours walking around the colorful streets.

Before beginning my walk around Old San Juan, I did spend a few minutes looking at a map. I wanted to make sure that I would visit some of the key tourist sights of Old San Juan during my walk.

As I entered the narrow streets of Old San Juan, I quickly disregarded the route I had mapped out. Walking around Old San Juan, I quickly was able to immerse myself in the narrow streets, Puerto Rican culture, and colorful buildings. Old San Juan is a truly historic Old Town that feels like going back in time.

During my time walking around Old San Juan, I didn’t make any purchases. What I did do was zig-zag the streets and take in the colorful scenery. Every block, it seemed that there was a beautiful sculpture, fountain, or building.

Even the fast-food restaurants had a historic look to them. While photographing the Subway, I was approached by a group of school children who were walking home from school. One of them asked me why I was taking a picture of the Subway. I explained that in Minnesota, our subways were not located in colorful buildings. The student laughed and walked around.

I am sure that I stood out as a tourist as I was the only one photographing the Subway and Burger King.

As I continued walking around Old San Juan, I eventually made my way out of the narrow streets onto what seemed to be the main road. This road led me to the San Cristobal Fort, where I would spend part of the afternoon looking at the historic fort.

I enjoyed walking around Old San Juan, on my own, without taking a tour. I didn’t feel a guide was necessary, as I wanted to experience the culture and look at the beautiful architecture.

If you would like to take a tour, I have linked eight tours below. Please note that as an affiliate of Viator, I will receive a small commission if you book using one of my links. This commission is at no additional cost to you.

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El Morro Fort

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Walking Around San Juan

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OLD SAN JUAN FREE WALKING TOUR

WELCOME TO PUERTO RICO!

Travel. Learn. Discover.

  WHAT TO EXPECT:

Enjoy a nice walking tour through Old San Juan, the second oldest city in America and the oldest in the U.S.A. For centuries, the city of Old San Juan was an important military base surrounded by fortifications and walls. This tour invites you to see San Juan through a local’s perspective, learn the history of the forts, walk through the colonial houses, and enjoy the eternal summer of the island and feel the essence and the truth of Puerto Rico. 

- The tour lasts approx. 2 hours -

Free Walking Tour: Old San Juan

*Maximum 5 per booking*

Offered Daily

Duration Varies

Free Walking Tour: Art District

*Santurce through Cerra St.*

1 hr 30 min

Private Tour

Through the Old San Juan

Start in $200

Pick-Your-Trip Tour

Through the Island (Max 3 ppl.)

start in $300

CONTACT US:

- For group tours & questions -

+1787-505-5581

Thanks for submitting!

MEETING POINT:

*The tour starts everyday at 10AM*

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Printed on 04 May 2024 from PuertoRicoDayTrips.com

Self Guided Walking Tour of Old San Juan – Part 3

Part 2 of our Old San Juan Self Guided Walking Tour series started at El Morro and ended back at La Casita. This article will pick up where the prior one left off.

This time we will go east from La Casita . With the Casita to your back, cross the street and continue along the waterfront (the bay will be on your right) just a little bit. On the corner is the Puerto Rico Tourism Company offices. They offer air conditioning and information . Stop in!

After you’ve cooled off, head back toward the La Casita and turn right at the corner onto San Justo Street. Go up 3 blocks and you will be on Fortaleza Street . This is one of the big shopping streets – stop in and treat yourselves to all sorts of "must-haves"! From jewelry to Puerto Rican crafts to clothes (famous maker and beach wear) to that last minute souvenir for Aunt Milly. If you want to shop, you can head left or right on Fortaleza. A neat store for vibrant PR art and crafts is “The Handcraft Store” , which is right here on the corner of San Justo and Fortaleza. Once you are done shopping and you want to continue on this tour, you will want to turn right onto Fortaleza (heading east).

As you walk down Fortaleza, you will come to two museums on your left – Casa de la Familia and Museo de la Farmacia , but they are both now closed.. Both are in the same building and both are free. The first floor houses the Pharmacy museum, upstairs is furnished as a upper class Puerto Rican home from the 1800’s. These will give you an idea of what life was like back in the old days. The placards in the museums are only in Spanish, but the tour guide in the museum is bi-lingual and can explain things for you. Admission to both museums are free, but they are open (if you are lucky) Wednesday- Sunday 8:30am-4:20pm (closed 1 hr for lunch 12-1pm). Allow 15 to 30 minutes.

As you continue walking down Fortaleza Street to the east, you will also notice many great places to eat – you are in the "SoFo" (South Fortaleza) area. Check out the menus that are posted outside each of the restaurants. Any of these restaurants would be a good choice for lunch or dinner.

At the end of Fortaleza, bear to the left and walk through Plaza de Colon . Here you’ll find a statute of Christopher Columbus ("Cristobal Colon" in Spanish) . Walk diagonally the the left through the plaza so that you are on the next street (San Francisco). From this end of the plaza, you’ll be able to see the San Crisotbal Fort. You can get into the fort by walking up to the doors through the parking lot, or by walking up the hill on Norzagaray Street.

Castillo de San Cristobal (San Cristobal Fort) was built in 1634, and completed in 1771. It was built to protect the city from sea and land invasions. The for is 150 feet high, and is a great example of the strategic skills used to make these defenses. This fort is actually a number of different units connected by tunnels, each unit being self-sufficient if another part is invaded. This fort has a wonderful dungeon that you can visit and see the doodling of prisoners on the walls. You can also see some damage the fort sustained during some of the battles. This fort is a World Heritage Site, and National Historic Site, administered by the US National Park Service. The fort is open to the public daily (except Thanksgiving, Christmas and New Years Day) 9:00 am to 6:00 pm . There is a small admission fee ($10 adults).

After you’re finished at Fort San Cristobal, you can head back down into the city, or you can continue along the north edge of the city (with the ocean to your right) and head back toward El Morro . Or, check out our next installment…. part 4 of our walking tour where you will go eastwards and see the newer sections of OSJ, including the Capitol Building (if it is open, go inside- it is beautiful.). Enjoy your visit Viejo San Juan!

Plan at least one full day to visit the streets and museums of Old San Juan.

PuertoRicoDayTrips.com assumes no responsibility regarding your safety when participating in the activities described in this article. Please use common sense! If your mother or that little voice in your head tells you that you are about to do something stupid … then don't do it! Read more about Safety →

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