29 Best Things To Do In Old San Juan (2025)

Looking for the best things to do in Old San Juan Puerto Rico?
My trip to Puerto Rico far exceeded my already high expectations. I knew it would be great, but let me tell you, it was ahhmazzing! And Old San Juan is a huge part of why I loved this vacation so much.

Old San Juan in Spanish is Viejo San Juan. It’s a must-visit destination, and not just as a stopover spot. Yes, the main airport in Puerto Rico is in this capital city, so you are likely to fly in and out of here, but what Old San Juan has to offer is worthy of at least a few days stay. This charming, historic district is packed with vibrant culture, stunning architecture, and plenty of things to see and do. 

Whether you’re a history buff or just someone looking to soak up the local vibes, Old San Juan has something for you as part of your Caribbean vacation.

Let’s dive right into some of the best activities and sights you won’t want to miss!

Here are the 29 Best Things to do in Old San Juan

The order of this list takes into account what I consider to be historically significant, my opinion of architectural beauty, some unique cultural experiences, and overall, regular visitor enjoyment! I encourage you to pick and choose according to your preferences.

Initially, we considered taking a guided walking tour, but chose instead to do a self-guided tour using the All Trails Map. It worked out great and allowed us freedom to stop when we wanted, pick it up again later, veer off when we saw something else we wanted to check out, etc.

Short on Time? Here are the Top 10 Must-See Spots!

1. Castillo San Felipe del Morro (El Morro)
2. Castillo San Cristóbal
3. La Fortaleza – Palacio de Santa Catalina
4. Catedral de San Juan Bautista
5. Paseo de la Princesa (Princess Promenade)
6. San Juan Gate
7. Casa Blanca
8. Capilla De Cristo
9. Parque de las Palomas (Pigeon Park)
10. Calle del Cristo

Click on the Google Map for the 29 sites in Old San Juan.

#1 Castillo San Felipe del Morro (El Morro)

501 Calle Norzagaray Open – 9-5 daily

Visit the remarkable site, not just for the view, but check out the history of this place!

The fortress, built in 1539, stands atop the 140 foot high promontory on the edge of the old city at the Atlantic Ocean. (I had to look up what a promontory is! In case you don’t know, it’s a raised mass of land that projects into water, like a giant cliff-peninsula.)

This fort was not completed until 1790 and was the most feared of all the Spanish forts that were built in the Americas. It was designed to be the most strategic protection against attack and could withstand cannonball fire.

After multiple failed attacks by the British and the Dutch, destruction by fire, and being rebuilt, eventually, El Morro could no longer defend itself. The Spanish American War in 1898 marked the beginning of the United States rule in the region. And by 1949, El Morro became part of the National Park Service and in 1983 earned its World Heritage Site status.

#2 Castillo San Cristóbal

501 Calle Norzagaray – open 9-5 daily

Yes, Old San Juan has 2 fortresses! This is the largest fort built by the Spanish in the New World.

After the English and the Dutch attacks, the Spaniards needed to create another stronghold to protect themselves. San Cristobal took 150 years to complete and is on the coast, a short distance east of El Morro.

This fort has so many interesting features – a moat and a web of tunnels to protect soldiers and store gunpowder, bomb proof rooms, cisterns that can hold 800,000 gallons of rainwater still used today, and most fascinating is the dungeon with a prisoner’s drawings from the 18th century. A friar was chained in the dungeon for over 20 years when accused of murder!

The World War II bunker is now the visitor’s center and the views on the hill are stunning. This site is also in the National Park Service and became a UNESCO World Heritage Site in 1983.

#3 La Fortaleza – Palacio de Santa Catalina

63 C. de la Fortaleza – Tours only M-F 8:30 – 3:30

You may be expecting to see Fortaleza Street leading to the mansion covered in bright umbrellas overhead. However, on our visit, that street was blocked off with police barricades and there were no umbrellas hanging!

La Fortaleza, also known as Palacio de Santa Catalina, was originally part of the Spaniard’s effort to protect the island from attack, however, it became the official residence of the governor of Puerto Rico in the 1600’s and has since housed over 170 governors and families.

#4 Catedral de San Juan Bautista

151 Calle del Cristo – 9-4 daily

This beautiful cathedral is a somewhat unassuming medieval church structure from the outside, and yet inside is a magnificent space with beautiful ceilings and alter. It’s the second oldest cathedral in the Americas and was originally built in 1511. After a hurricane destroyed the wooden building, a new one was built in 1535. One of its most notable features is the tomb of the Spanish explorer Ponce de Leon. The church continues to be fully operational offering services in addition to being open to touring visitors.

#5 Paseo de la Princesa

Open 24 hours

The Paseo de la Princesa, or Princess Promenade, built in 1852, is the .5 mile walkway along the water outside of the old city wall in San Juan. It’s considered one of the world’s most beautiful walks. Parts of the esplanade has charming old street lamps leading up to the famous Raices Fountain. You’ll walk for the gorgeous views, the iguanas crawling on the rocks by the water, and the hundreds of kitties who lay sleeping in the sunshine by the wall.

It was built in honor of Princess Asturias Infanta Isabel. She was the oldest daughter of the famed Queen Isabelle II of Spain. The Princess and her mother are known for their dramatic life filled with things like illegitimate children, wars over the throne, and being trapped in a tower.

#6 Caleta de San Juan – The San Juan Gate

Paseo de la Princesa

This is the very large and historic gate, painted red, that was built in 1635 as the main entrance to the walled city. And this was a great spot for us to stand under while waiting for the downpour to stop!

 The gate is 16 feet tall and was meant to both great visitors but also protect the city from invasions. It was always heavily guarded and closed at night.

The top of the gate has a Latin inscription “Benedictus Qui Venit In Nomine Domini,” which means“Blessed is the one that comes in the name of God.”

Remember that as you walk through this gate, you’re on the same path as all the important dignitaries from centuries of Old San Juan. You can access the gate from inside the city or while walking along the Paseo de Princesa. From the promenade, turn right at the Raíces Fountain. 

 #7 Museo Casa Blanca

1 C. de San Sebastián – Open Wed – Sun 8-4

This home and fort was built in 1521 for Puerto Rico’s first governor and his family, Juan Ponce de León. Unfortunately, he died in Florida before even moving in, but his family lived there. It is known for being the oldest occupied house in the entire Western Hemisphere! It is now used as a museum with exhibits of 16th and 17th century art.

#8 Capilla De Cristo – Chapel of Christ the Savior

At the end of Calle de Cristo

This chapel was built between 1753 and 1780. Legend has it that the Chapel of Christ the Savior was erected to honor a miracle. It is said, that in the year 1750 the Cristo Street was host to a horse race where one of the participants could not stop his horse and fell off the cliff. The Secretary of Government at the time, Don Tomás Mateo Prats is said to have invoked the Santo Cristo de la Salud and that the young man who fell off the cliff was saved. And so, the Secretary of Government ordered the construction of the chapel on sight to honor the miracle. It was later revealed that the young man died, but still, this chapel has a distinct spiritual feel to it. How to better start your journey than in this miracle sight!

#9 Parque de las Palomas – Pigeon Park

C. Tetuán – Tues – Sun – 9-6

This unusual park behind a rod iron gate not only offers beautiful views of the water, but is home to hundreds of pigeons. Not my thing, but lots of visitors buy dried corn there to let the pigeons feed out of their hands. They will literally stand on your head, eat out of your hand, and fly around begging for more. The trees and public art in the park are lovely, not to mention the great photo ops!

#10 Calle del Cristo

Calle de Cristo

The main street of Old San Juan is the cobblestone street named Calles de Cristo (Christ’s Street). It’s a bit of a steep hill that flattens out as it approaches the water. Not only are there many important sites along this street, but it’s also the primary shopping, boutique, gallery, and restaurant stretch in Old San Juan.

You will no doubt end up strolling along this street passing the cathedral and heading toward the Chapel and Pigeon Park.

#11 Museo de Arte e Historia de San Juan

150 Calle Norzagaray 9-4 Wed – Fri, 10- 4 Sat, 10- 5 Sun

The Museum of Art and History is a great museum to pop into on a rainy afternoon. The building once was the city’s marketplace and is an example of the Spanish colonial architecture that you’ll see throughout the city. The museum exhibits include historic photographs, contemporary art, and religious statues known as santos.

#12 Museo de Las Américas

C. Beneficencia – Open Mon-Fri 9-12, 1-4, Sat-Sun 11-4

This museum, located in the historic Cuartel de Ballaja, a Spanish colonial military barracks,is dedicated to the community and cultural heritage of Puerto Rico. You’ll find exhibits on Folk Arts, African Heritage, Conquest and Colonization, and temporary exhibits as well.

#13 Galería Nacional

Calle del Cristo – Tues – Sat 9:30 – 5:30

The National Gallery is one of Puerto Rico’s premier art museums. It houses the  largest collection of Puerto Rican paintings from the 18th century to modern times. The historic building once was a monastery of the Dominican Order built in 1523. Sadly, we were unable to add this to our itinerary and its top of my list for next time!

#14 Plaza de Armas

Calle San Jose

This plaza was originally designed in the 1520’s but much later became the center square of Old San Juan. Known as The Plaza de Armas of San Juan it’s one of the nicest places to stroll, relax, listen to street performers, and have a coffee or empanada from a nearby kiosk. We passed through here many times on our visit and found different things going on each time.

#15 Plaza del Quinto Centenario – Plaza del Tótem 

Calle de Cristo

This is a modern plaza on the waterfront near El Morro and other historic sites. You’ll find the giant totem pole here which stands 40 feet tall. The totem was created by artist Jaime Suárez using broken pieces of pottery representing the archeological finds of the indigenous Taino people of the island. A reminder of the harsh history of the Europeans taking over Puerto Rico from its native inhabitants.

#16 Fuente Raíces – Raices Fountain

101-103 Paseo de la Princesa

This magnificent fountain at the end of the Paseo de la Princesa, Princess Promenade, was erected in 1992 for the opening of the promenade and to honor the 500th anniversary of the Spanish finding America. The beautiful figures represent the indigenous peoples of the island, the Taino as well as those with African and Spanish heritage.

#17 San José Church

197 Calle O’Neill

The San José Church, is another of Old San Juan’s most important churches. Built in 1532, this 16th century Gothic building still stands as the second oldest church in the Americas.

This is the site of Juan Ponce de Leon’s first resting place before he was moved to the cathedral. His family remains interred here, as does the famous artist José Campeche.

While this church survived 500 years of wars, hurricanes, floods, and other disasters, it was found to be an endangered historic site, it underwent renovations from 2003 until recent years. 

#18 Santa Maria Magdalena de Pazzis Cemetery

Calle de Cemetery

In 1863, designed by Carmelit nuns, this beautiful cemetery was founded to be the final resting place for many of Puerto Rico’s most prominent citizens.

The site is ideal – on a hill overlooking the ocean. It’s placed in between the El Morro Fort and the La Perla neighborhood.  The old section of the cemetery is for Puerto Rico’s most notable people.

It’s quite a beautiful spot overlooking the water, against the blue sky with the backdrop of the large green lawn and fort. You can roam through this peaceful cemetery during the day.

#19 El Capitolio – The Capital

1 Democracy Square

Puerto Rico’s Capitol building, located outside the Old San Juan walls is a 1920’s Beaux Arts style building covered in white marble. It was inspired by the Pantheon in Rome and the New York City Library. This is where the Legislative Assembly sit and is on the registry of National Historic Places. Visitors are welcome in private tours only.

#20 Galería Botello 

Calle de Cristo

I love a gallery that is like visiting a museum!

The Botello Gallery is just about a block from El Convento, across from the cathedral. In this 350 year old Spanish building, you’ll find works from the famous Puerto Rican artist, Angel Botello. He was named the “The Caribbean Gauguin,” for his images of island life.

Botello moved to P.R. after being exiled from Spain during the 1940 civil war, and then living in the Dominican Republic and Haiti for a time.

Botello opened his gallery in 1953 and devoted his life’s work to painting, sculpture, and graphic arts. 

#21 Casa Rosa

Calle de las Monjas

This historic and very picturesque and bright pink  building was built in 1812 as an army barracks for Spanish troops. It later became an officers’ quarters. It now houses a day care center for the children of government workers.

#22 Teatro Tapita

Calle Fortaleza

If you’re looking for a fun theater experience, (in Spanish) then visit Teatro Alejandro Tapia y Rivera. It’s the oldest, still operating, theater in the US.

Built in 1832, the theater has 640 velvet seats, balconies, and apparently has great views from every spot. The building itself is a classic and stands next to the big blue casino across from the Plaza Colón. The theater is a venue for both drama and comedy.

#23 Department of Treasury Annex

Plaza de Armas

As part of the main Plaza de Armas square, the Treasury Annex was home to the government’s money in Puerto Rico. It also became the headquarters of the early legislative branches.

#24 La Perla

Next to the Cemetery

Just next to the Cemetery, outside of the old city is what historically has been the poorest section of San Juan.

This brightly covered barrio is now being revitalized, but has the history of being where the slaves and poor lived.

Safety may still be somewhat of an issue. Be respectful and mindful as you wander through this vibrant, colorful neighborhood next to the old city walls.

#25 Seminario Conciliar de San Ildefonso

52 Calle de Cristo

This is the original seminary school for training priests that was built in 1832. Students of all walks of life studied here and it became that center of public education.

Queen Isablel Segundo allowed departments of physics, literature, math, and other topics to be taught here.

In modern times, the school has become the Center for Advanced Studies of Puerto Rico and the Caribbean.

#26 Castillo de San Jerónimo

1 Calle Los Rosales

Just outside of the old city is yet another fort!

Fortín de San Gerónimo de Boquerón is a small fort located on the Condado Lagoon, in the historic neighborhood of Miramar.

This fort was built in the 18th century. This site is likely less busy than the forts in Old San Juan but also packed with history!

#27 La Playa El Escambron

Calle San Agustín

We had almost three days in Old San Juan and chose to save our beach time for Rio Grande and Rincon, so we didn’t spend a beach day in the city. However, obviously, the old city is an islet and surrounded by water and people do love the beaches in San Juan. The beach closest to the old city is a 30 minute walk and is called Playa El Escambron. People enjoy the warm water, the trees for shade, and the public restrooms and facilities. Check it out!

#28 Nightlife in Old San Juan

Old San Juan has quite the reputation for having an “electric” and exciting nightlife scene. There are plenty of restaurants and bars throughout the old city to checkout. Probably the most famous is Barrachina, home to the first Pina Colada. You’ll find this venue at 104 Calle de la Fortaleza.

#29 Puerta de la Bandera – Flag Door of Old San Juan

  51 Calle San Jose

In 2012 this door to an abandoned and historic building was painted with the bright red, white, and blue Puerto Rican flag and became a populare tourist spot. In 2016, artists repainted the door to black and white, representing resistance and hope. The door is now very famous on social media and is a popular photo op.

Another flag is painted on a gate at the corner of  Calle de la Virtud and Calle Imperial.

This flag also appears in many earlier photos with pristine bright paint, however, you can see in my photo that it is now covered in graffiti. Maybe those photos have edited the graffitti out? 

Where to Stay in Old San Juan

El Convento Hotel – 100 Calle del Cristo,

I am only going to recommend one hotel for Old San Juan. This is the hotel we stayed at and absolutely loved. I did not spend time looking into other hotel choices for you all, as I usually do, because there’s no need! This place is wonderful!
Stay at this 350 year old former convent, built in 1646, with its modernized and renovated rooms, beautiful courtyards, and charming rooftop pool and hot tub. The service is 5 star worthy and the entire feel is both elegant and relaxed.

Hotel El Convento could not be in a more perfect spot for visiting. You can literally walk out the door and be in the center of everything you want to see and do in Old San Juan.

Where to eat in Old San Juan

Ok, I confess, we found one restaurnt that we loved so much, we ate there 3 times!!! I’m not kidding!

It is called El Champi at 72 Calle Caleta and it is directly across the street from Hotel El Convento. It’s a Spanish Tapas restuarant with lovely indoor and outdoor seating. great staff and amazing food!!!!

We also had delish gelato at the famous Anita’s on Calle de Cristo.

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Is San Juan Safe?

Old San Juan felt very safe while we visited. In fact we all mentioned it often, “its so clean here…we feel very safe here.” There is a heavy police presence in the area because of tourists, because of all the important historic sites, and because of the Governor’s Mansion and all the government buildings.

The La Perla neighborhood is said to be the oldest and last remaining “slum” of Puerto Rico. We did not spend time there, but it is also in a period of revitalization and has an active police presence as well. It is right on the water, just outside of the walled city, and is starting to attract visitors who want to explore and take photos.

Old San Juan was hit by several hurricanes in recent years. I certainly am not a weather expert, nor can I advise you about avoiding hurricanes if you travel to Puerto Rico. But I can tell you a few facts.

Hurricane season in Puerto Rico is reported as June through November.

Hurricane Maria (2017): Hurricane Maria was a Category 5 hurricane that devastated Puerto Rico in September 2017. There was widespread damage across the island, including in Old San Juan.

Hurricane Fiona (2022): Hurricane Fiona, was a Category 1 hurricane that struck Puerto Rico in September 2022. Old San Juan and other parts of the island were affected with flooding, power outages, and infrastructure damage.

The best time to visit Old San Juan

I visited in mid May and the weather was ideal. We had lots of hot and steamy days, which I love! It was never too hot to enjoy the sights. The temps ranged from 75 degrees to 85 degrees. We experienced a few downpours that lasted from a few minutes to about an hour, but again, nothing that stopped us from enjoying our time.

Generally expect what is called ‘tropical weather” throughout the year. This means warm and muggy with spurts of rain. Just how I like it!

• The Summer temps range from high 70’s to high 90’s. August is considered the rainiest month.
• The Fall average temps are in the 80’s.
• The Winter is considered the dry months and the best time to visit with temps in the 70’s and low 80’s.
• The Spring is considered warm and sometimes wet with temps in the 80’s and brief rain showers.

Is Puerto Rico part of the United States?

Yes it is and if you are traveling from the US, you do not need a passport, do not go through customs, and use US dollars. It’s just like going to Hawaii, part of the states, but off the mainland.
And here are some other interesting facts:

• Approximately 3.5 million people live in Puerto Rico and it’s the largest of the US Territories.
• Puerto Rico, like the Virgin Islands and Guam, is a “territory” under the sovereignty of the United States federal government. 
• Puerto Rico is not part of any state, nor is it a state itself, but it has its own organized self rule government.
• Puerto Ricans are US citizens, and have been since 1917. 
• Puerto Ricans do not have voting representation in Congress and therefore can’t vote in presidential elections.
• Puerto Ricans can, however, vote in presidential primaries and can send delegates to the Democratic and Republican conventions. 
• Puerto Rico has a delegate in the House of Representatives who is not allowed to vote on the floor, but can vote on some matters within committees.
• Puerto Ricans pay some federal taxes, but not all categories of federal taxes.
• For decades, Puerto Rico becoming a 51 state has been debated. Puerto Ricans have voted six times to become the 51st state, most recently in 2020 with a majority of 52%. The US Congress passed the process onto the House Committee of Natural Resources. The bill was again reintroduced in 2021 and again in 2022. I read that the bill passed in the House and “died in the Senate.”

And there you have it – 29 amazing things
to do in Old San Juan.

In a nutshell…

San Juan gave me so many things I love when traveling – a beautiful hotel, a charming and historic city, beautiful art and food, and really nice people! Oh, and great weather!

Old San Juan is quaint like a European hidden gem  and filled with excitement like New York City and offers cultural history like San Francisco!

From exploring ancient forts and wandering through colorful streets to enjoying delicious local cuisine, Old San Juan is so happening! And the most amazing opportunities to swim in a bioluminescent bay is just a few hours away!

Whether you’re here for a day or a week, you’re sure to fall in love with the rich history, friendly locals, and stunning scenery.

Pack your bags, grab your camera, and get ready for an unforgettable adventure in Old San Juan. Happy travels!

xx,
Carrie