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The Best Things to Do in Old San Juan, Puerto Rico

With beautiful natural landscapes and over five centuries of history, San Juan, the capital of Puerto Rico, is a must-visit destination in the Caribbean. On a recent visit, we spent a few days in Old San Juan and came away captivated. Read on to discover the best things to do in Old San Juan!

Old San Juan, or Viejo San Juan, is the historic part of the lively Puerto Rican capital. Its cobblestone streets and colonial architecture will remind you of Spain, but Old San Juan also has its own unique ambience.

Building Old San Juan Puerto Rico
Beautiful architecture and bright colors are everywhere in Old San Juan!

Located on a small narrow island, Old San Juan was settled in the early 16th century. Heavily fortified to stave off attacks from other nations looking to invade, Old San Juan is a National Historic Landmark District.

The Best Things to Do in Old San Juan

Without question the most interesting part of the city, Old San Juan deserves at least a couple of days in your itinerary for the Puerto Rican capital. You’ll find a wealth of activities and sights in Old San Juan to keep you engaged for much longer, but in two full days, you can explore quite a bit of the fascinating district.

Facade Old San Juan PR
A stunning colonial facade in Old San Juan

Old San Juan is walkable: in fact, walking the streets was one of the most enjoyable things we did here. Get set to enjoy amazing architecture, splendid sculptures, lively squares, and delicious food and drink during your time in the old city.

Here, then, are the very best things to do in Old San Juan:

#1 Visit the historic El Morro Fort

Part of the San Juan National Historic Site and UNESCO World Heritage site, the Castillo San Felipe del Morro is one of the city’s most popular attractions, and should be at the top of your list of places to visit in San Juan.

El Morro in San Juan Puerto Rico
The beautiful main courtyard at El Morro

Built by the Spanish over a period of 250 years to quell attacks on the city from the sea, the impressive fort sits on a high rocky headland overlooking San Juan Bay. You’ll be impressed even before you enter! In front of the fort is a vast green lawn, where locals fly kites on good weather weekend afternoons.

El Morro San Juan Puerto Rico
Admiring El Morro in Old San Juan

The fort is built over six levels, and you can explore many parts of it, using the map you’ll receive when you enter. Gawk at the gorgeous garitas, from where sentries looked out in times past. Get great views of the water from the Cannon Water Battery. Admire the Torre Antigua.

Lighthouse at El Morro San Juan PR
The first lighthouse in Puerto Rico was built at El Morro

The fort is open everyday from 9 a.m. until 6 p.m. (except for Thanksgiving, Christmas and New Year’s Day). The entrance fee covers both El Morro and Castillo San Cristobal. National Parks passes are valid at both forts.

Read next: A Guide to Visiting El Morro in San Juan, Puerto Rico

#2 Explore the fascinating Castillo de San Cristóbal

Old San Juan is home also to the Castillo de San Cristóbal, built by the Spanish to protect against land-based attacks. Also part of the National Historic Site and UNESCO World Heritage site, the Castillo de San Cristóbal was built over a period of 150 years.

Castillo San Cristobal San Juan Puerto Rico
Walking one of the terraces at the fort on a beautiful day

Also located along the water, the San Cristobal fortress features an impressive main entrance and is built over three levels. From the top level, you get beautiful views over the water as well as over the city.

A View from the Castillo San Cristobal in San Juan Puerto Rico
A view of the Puerto Rican Capitol from the Castillo San Cristobal

You can wander around the fort, walk through the tunnel, admire the old cannonballs, look out from a sentry box, and view the old military quarters. There are information panels all over the fort, if you wish to learn more about the fort and the history of Old San Juan.

Sentry Box Castillo San Cristobal San Juan Puerto Rico
A sentry box just outside Castillo San Cristobal

Read next: A Guide to Visiting Castillo San Cristobal in Old San Juan

#3 Take a peek at La Fortaleza

La Fortaleza is the official residence of the Governor of Puerto Rico. Its powder blue facade, architectural detail, and stunning location on a bluff overlooking the water make it one of San Juan’s most attractive buildings.

La Fortaleza San Juan PR
La Fortaleza has a stunning location!

Originally built as a fortress to defend San Juan’s harbor, La Fortaleza is part of the San Juan UNESCO World Heritage site. You can tour parts of the interior on a guided tour. Tours are offered on week days, but check when you visit as they may be canceled for various reasons.

#4 Step into the San Juan Cathedral

The San Juan Bautista Cathedral on Calle del Cristo is both historic and beautiful. It is the second oldest church in the Americas, and the oldest in the United States.

San Juan Cathedral Puerto Rico
Looking up into the dome of the San Juan Cathedral

The structure you see today was built in the mid 15th century, after the original wood building was damaged by a hurricane. The beautiful pale yellow facade, accented with white, looks stunning.

San Juan Cathedral in Puerto Rico
The beautiful pale yellow facade of the cathedral

Step inside to view the gorgeous interior. The cathedral holds the remains of Juan Ponce de León, the famous Spanish explorer. You will see lovely works of art and stained glass windows. Many works of art are sadly reported lost to looting by attackers in colonial times.

Interior of San Juan Cathedral in Puerto Rico
Stained glass art in the cathedral

#5 Admire the decorations at Calle de la Fortaleza

Calle de la Fortaleza is a street in Old San Juan that runs up to the Governor’s mansion. It is a lively street most of the day and into the evening. During the two days we were in the city, there were some performances on the street, with lots of music and dancing.

The street is known for its decorations. When we were planning our visit, I saw photos of colorful umbrellas hanging above the street, and I was hoping to get some photos of my own. When we were in town, however, a gigantic flag of Puerto Rico was stretched above the street.

Calle de La Fortaleza San Juan Puerto Rico
The Puerto Rican Flag draped over Calle de la Fortaleza
Fortaleza in Old San Juan
Walking down Calle de la Fortaleza

We walked the street, under the canopy of the flag, to the gates of La Fortaleza, where we saw a lovely Nativity display for Christmas. Visit early in the day to enjoy the historic feel of the street without crowds, and later in the day to enjoy all the goings-on.

WHERE TO STAY IN OLD SAN JUAN!

Without a doubt, Hotel El Convento is the most atmospheric place to stay in Old San Juan. With a fabulous location in the heart of the old district, just next to the San Juan Cathedral, the hotel is an architectural sight in its own right. As its name suggests, the place was a convent in times past, and the rooms still retain some of that ambience.

With an impressive foyer, beautiful old paintings, and a charming courtyard, Hotel El Convento looks completely in place in its historic surroundings.

Our bed was extremely comfortable, and we loved coming home to the well air-conditioned room after a day out in the warm sun. We enjoyed the turndown service, and the complimentary wine and cheese in the evenings.

The infinity pool on the roof is a great place to soak and enjoy a drink, and the restaurant and bar are lively in the evenings.

We loved our stay at Hotel El Convento! Book a stay here

*****

Another great option in Old San Juan is the Sheraton, with its fabulous views of San Juan Bay, and a location that is within easy walking distance of most major sights in the Old City.

The Sheraton features a rooftop swimming pool, onsite dining options, and the beds are rated super comfy. Book a stay here

#6 Visit Casa Blanca, the home of Juan Ponce de Leon

If you visit one museum in San Juan, make it Casa Blanca, built for the explorer Juan Ponce de Leon. Touring the historic house and its lovely garden is one of my most favorite memories from our visit to Old San Juan.

Casa Blanca is actually a fortification, built in the 16th century. Although it was built as the residence for Ponce de Leon, he died before he could move in. His family did live here.

Tiled staircase Casa Blanca Old San Juan PR
Tiled staircase in Casa Blanca

The interior contains simple furnishings: a living room with beautiful views, a dining room, and a bedroom. The rooms upstairs are not furnished, but we saw some lovely signed murals on a couple of walls.

Mural Casa Blanca San Juan PR
Art in one of the empty rooms at the Casa Blanca

The gardens are simply gorgeous. From the terraces, you get great views of the water, and the plantings are beautiful. Casa Blanca is definitely a must-visit attraction in Old San Juan!

Terraced Gardens Casa Blanca Old San Juan PR
Walking through the gardens at Casa Blanca is a joy

#7 Wander the cobblestone streets

Old San Juan is very historic, very colorful, and a joy to stroll. The cobblestone streets are reminiscent of Europe, but with a unique character all their own, and you’ll come across lively squares, beautiful architecture, and stunning Spanish tile work.

Old San Juan Puerto Rico
An alley in Old San Juan

San Juan’s old cobblestones have a lovely blue sheen on them. The original cobblestones were actually salvaged ballast from ships that arrived from Europe in the 18th century. Many have since been replaced, but you can still see the original blue stones in streets like Calle Cristo.

Cobblestone street in Old San Juan Puerto Rico
The cobblestone streets of Old San Juan

The streets are narrow, but full of character. Neighborhood cafes and bars offer great spots for a rest and some people watching. We clocked up lots of steps just wandering around in Viejo San Juan, and it is easily one of the most fun things to do here.

If you want to learn about the city and its history and culture as you walk, join a guided walking tour! It’s a great way to get acclimated and one of our favorite activities in any new destination. Book this highly rated walking tour now!

#8 Admire the cool facades

Looking for lots of color to light up your Instagram account? You’ll find walls in every color of the rainbow in Old San Juan. The bright in-your-face colors reminded me of the colorful island of Burano outside Venice.

Facade Old San Juan Puerto Rico
You will see facades in so many bright colors in Old San Juan!

While the colors of the facades are lovely, don’t miss the beautiful detail you’ll find on many buildings. Beautiful balconies and windows, touches of greenery and flowers, and decorative designs in tile and metal will make you want to stop every steps for yet another photo.

Colorful Facade in Old San Juan Puerto Rico
Beautiful color and detail on a facade in the old city

On some of the streets, the house numbers are encased in beautiful art. And finally, many of the doors and windows are gorgeous. Give yourself lots of time to admire the houses of Old San Juan!

House number Old San Juan Puerto Rico
Isn’t that a beautiful way to display a house address?
Window Old San Juan Puerto Rico
A pretty window in Old San Juan

#9 Walk the old cemetery

Just outside El Morro, you’ll find the Old San Juan Cemetery. Built overlooking the water and located between El Morro and San Cristobal, the cemetery makes for an interesting stop if you have the time.

Old Cemetery San Juan PR
Looking down on the old cemetery from the street

Santa Maria Magdalena de Pazzis Cemetery, to give the cemetery its official name, holds the remains of many famous citizens of San Juan. It contains a wealth of white stones, and literally dazzles in the sun against the bright blue of the ocean.

View of Old San Juan Cemetery San Juan Puerto Rico
The white tombstones at the cemetery, seen from El Morro

You have to walk through a tunnel to get to the main gate of the cemetery. There’s generally an attendant on duty when the cemetery is open, and you can walk among the tombstones and step into the little chapel.

#10 Snap a photo of colorful La Perla

Between El Morro and the Castillo San Cristobal lies the community of La Perla. You can see the colorful houses as you walk from one fort to the other. Take photos from the street above, or from one of the forts if you have a zoom lens. La Perla is one of the most Instagrammable spots in Puerto Rico!

La Perla from Castillo San Cristobal San Juan Puerto Rico
The colorful houses of La Perla seen from the Castillo San Cristobal
La Perla San Juan Puerto Rico
The houses of la Perla from the street above

Along the road that connects the two forts, you can see some street art as well. And, if you look closely, remnants of old Spanish tile work as well.

Street Art San Juan Puerto Rico
Street art near La Perla

#11 Admire the charming Casa Rosa

You’ll never believe it when you set eyes on the pretty-in-pink Casa Rosa, but it was actually built as barracks for Spanish soldiers. Later it served as officers’ quarters.

Casa Rosa Old San Juan Puerto Rico
The Casa Rosa looks pretty in pink!

Later the restored villa became a crafts museum, serving as a repository for the creative talents of Puerto Rican artists. Today it is a day care center for the children of government employees.

Gate to Casa Rosa Old San Juan Puerto Rico
The beautiful front gate of Casa Rosa

Both functional and beautiful, the Casa Rosa makes for delightful photos. Stop by the Pink House when you are in Viejo San Juan, for a visual treat!

#12 Check out the gate of Old San Juan

Old San Juan used to be a heavily fortified walled city, and you had to go through one of its six gates to get inside. Today, La Puerta de San Juan is the only surviving old gate.

San Juan Gate Old San Juan Puerto Rico
La Puerta del San Juan was the principal entrance into the city in colonial times

The San Juan Gate served as the point of entry for people arriving to the city via the water. The gate is painted a lovely deep red on the outside, and the inscription at the top welcomes those “who come in the name of God.”

San Juan Gate Puerto Rico
Information about the San Juan Gate at the site

If you walk out through the gate from the city, you will find yourself on a beautiful walkway that hugs the water. And if you look up from the pathway, you can see La Fortaleza right above you!

Waterfront walkway Old San Juan Puerto Rico
The beautiful waterfront walk just outside the San Juan Gate

#13 Feed the pigeons at the Parque de las Palomas

I had never seen so many pigeons in so small a space before we visited Parque de las Palomas. The small park, on Calle de Tetuan, features mature trees and a cobblestone pavement, and is one of the more unique places to see in Old San Juan.

Parque de las Palomas overlooks the Bay of San Juan, and you get beautiful water views from here. But the star attraction in the park are quite definitely the hundreds of pigeons!

Park of the Pigeons Old San Juan
Beautiful views of the bay at the Park of the Pigeons!

If you enjoy feeding birds, you can buy some food from one of the vendors at the park. The pigeons aren’t shy, and we saw them land on the heads and outstretched arms of park visitors.

#14 Stroll through the Plaza de Armas

One of the main squares in Old San Juan, Plaza de Armas is lively during the day and into the evening and night. The square is lined with restaurants, cafes, and shops.

Building at Plaza de Armas Old San Juan
Beautiful building lining the Plaza de Armas

The square is a fabulous place for people watching. Just park yourself on a bench, in the sun or in the shade, and relax for a bit, watching locals and visitors go about their day. Here, too, you will see lots of pigeons!

You can also walk around and admire the architecture of the buildings surrounding the square, and view the fountain that depicts the four seasons.

Fountain at Plaza de Armas Old San Juan
The Four Seasons Fountain in the square

#15 Admire the totem pole at the Plaza del Quinto Centenario

Built in 1992 to commemorate the 500-year anniversary of the discovery of the New World, the Plaza del Quinto Centenario features the Totem Telurico, a 40-foot tall totem pole designed by Jaime Suarez. This tall sculpture is definitely one of the most popular Old San Juan attractions!

Totem Pole Old San Juan Puerto Rico
The Totem Pole sculpture in Old San Juan

Depicting the origins of the people of the New World, the ceramic sculpture looks spectacular if you see it on a bright sunny day, or looming up into the night sky. The plaza, with its fountains and sweeping staircases, is also worth a stroll.

#16 Enjoy the lights display at Cuartel del Ballaja

One of the fun things to do after dark in Old San Juan is to walk over to see the lights at Cuartel del Ballaja, the old military barracks building. We visited over the holidays, and the barracks were lit up in holiday shades of red and green.

Lights at the Old Military Barracks in Old San Juan Puerto Rico
Beautiful holiday-themed lights at the old military barracks
Lights at Old Military Barracks San Juan PR
It’s worth the walk to see the barracks lit up!

If you visit during the day, admire the gorgeous architecture, and pop into the Museum of the Americas on the second floor, or get a drink at the Don Ruiz coffee shop.

#17 Stroll the Paseo de la Princesa

Walking down the Paseo de la Princesa is a must-do when you visit San Juan. It’s a beautiful and historic walkway, dating back to the mid 19th century.

Paseo de la Princesa Old San Juan PR
The Paseo de la Princesa makes for a lovely stroll

The walkway hugs the city wall of Old San Juan, and is lined with mature trees. Along the way you can step inside a small garden, and admire the architecture of La Princesa, once a prison but now the offices of Puerto Rico Tourism Company.

Offices of the Puerto Rico Tourism Company in a former prison
The lovely building that used to be a prison

At the end of the promenade is the famous Raices fountain, with its beautiful sculptures. Walk up to the edge of the water for great views across the bay. If you continue around the corner along the water, you will some to the San Juan Gate.

View from Waterfront Old San Juan
A lovely view of the water

The city wall is lit up at night, making the stroll magical. And sunset is a great time to be at the water’s edge as well.

#18 Admire all the statues around town

As you walk around Old San Juan, you will see lots of lovely sculptures. The Raices Fountain is an impressive example. Made of bronze, it features dolphins, horses and people emerging from the water.

Raices Fountain San Juan PR
The stunning Raices Fountain stands by the water

Near the San Juan gate, don’t miss La Rogativa, another work in bronze that depicts a bishop and some women. According to local legend, the procession, when it happened in the late 1700s, actually disrupted a British invasion of San Juan.

Just outside the San Juan Cathedral, you’ll see some whimsical animal sculptures. And near Casa Blanca, stop to admire the statue of Eugenio María de Hostos.

Sculpture Old San Juan Puerto Rico
Statue of Eugenio Maria de Hostos

Of all the beautiful things to see in Old San Juan, I thought the various sculptures around town were some of the most beautiful.

#19 Do a fabulous food tour

One of the best parts of visiting Old San Juan is the fabulous food on offer in the old city: and the best way to experience all the culinary delights of the region is on a guided tasting tour with a knowledgeable local.

This highly rated 3-hour walking and tasting tour includes several delicious stops. You will also learn how mofongo, one of the staples of Puerto Rico cuisine, is made!

Admire Old San Juan’s architecture and learn about its history and culture on this fascinating food and culture tour. Book your spot now!

#20 Shop for souvenirs

You’ll see souvenirs for sale all around the old town, so if you love shopping, get ready to browse everywhere you go! From traditional lace to jewelry, you’ll be spoiled for choice when it comes to souvenir shopping in Old San Juan.

If you are looking for something unique, consider a vejigante mask: a colorful reminder of medieval Spain. Or shop for local jewelry: you will find gold and silver jewelry here, but also local designs made from glass or shells. You’ll find lovely ceramic items here as well.

And of course, rum (in many flavors!), and great coffee, are everywhere in Puerto Rico.

#21 Photograph the beautiful Capilla del Cristo

Old San Juan is home to lots of lovely structures, and the Capilla del Cristo is both stunning and historic. Built in the mid 18th century, the chapel is located close to the Parque de las Palomas, and is a must-see in Old San Juan.

Capilla de Cristo Old San Juan Puerto Rico
The Capilla de Cristo in Old San Juan

Local lore goes that a divine intervention took place at the site. A horse with a young rider, competing in a race, fell over the cliff. The horse reportedly perished, but the rider miraculously escaped death. The chapel was built at the site in recognition of the miracle.

The chapel was not open when we visited, but it makes for beautiful photos, so be sure to stop by!

#22 Do a night walking tour

While walking around Old San Juan during the day is awesome, also consider walking it at night as part of a guided tour, for a totally different and delightful experience.

Plaza de Armas Old San Juan at night
The Plaza de Armas is all lit up in the evening!

The old town takes on a mysterious old world aura after dark, with laughter and voices drifting out of dimly lit bars and cafes. Churches and historic monuments are illuminated, as is the city wall.

Capilla del Cristo Old San Juan lit up at night
The Capilla del Cristo looks beautiful lit up at night

On a guided walking tour, you will learn about the history of San Juan as you walk. It’s a great way to see the city at night without fear of getting lost. Definitely one of the best things to do in Old San Juan at night!

#23 Cool down with a local ice cream bar

Enjoying an ice cream bar from Señor Paleta is a quintessential Old San Juan experience, especially welcome on a warm day. The paleteria is located on Calle de Tetuán and boasts a wide range of unique flavors.

From coconut to tamarind and limonada to strawberry, the store features some fabulous sweet ice cream treats. We sampled quite a few of the flavors during our time in Old San Juan and every single one was delicious!

#24 Take photos of the cats of Viejo San Juan

Reminiscent of European towns along the water like Kotor in Montenegro and Dubrovnik in Croatia, Old San Juan is home to lots of cats. You’ll see them sunning themselves on ledges and walls, and slinking along the narrow alleys.

Cat in Old San Juan Puerto Rico
You’ll see lots of cute cats in Old San Juan!

Cats were likely brought to the city by Spanish sailors looking to eliminate rodents. Now you will see them all around town. Take photos, but don’t feed the cats. Consider donating to the local Save-a-Gato Cat Sanctuary instead. You can visit the sanctuary as well!

#25 Enjoy everything chocolate at Chocobar Cortés

From soup to sandwiches and desserts, everything on the menu at Chocobar Cortés features chocolate! My husband and I are both chocolate lovers, so we visited more than once during our stay in Old San Juan.

Chocobar Cortes Old San Juan Puerto Rico
The historic Chocolate Cortes

Try the grilled cheese with chocolate, or the roasted pumpkin soup with white chocolate. We thought both items were exceptional. And the desserts are to-die-for delicious.

Cheese Chocolate Sandwich Chocobar Cortes Old San Juan
The grilled cheese with chocolate is a must-have at Chocobar Cortes!

#26 Sail San Juan Bay at sunset!

For a truly magical experience, consider a sailing excursion in San Juan Bay in the evening, with the warm ocean breezes ruffling your hair and a brilliant Caribbean sunset to close out your day.

Old San Juan Puerto Rico
A view of La Fortaleza and Old San Juan from the water

The highly rated sunset sail excursion leaves from the pier at Old San Juan and lasts 2 hours. You’ll see El Morro and La Fortaleza from the water: the old city looks beautiful in the mellow light of late evening.

Sailing San Juan Bay in Puerto Rico
An evening sail in the Bay of San Juan is a magical experience

You can also do a 90-minute sailing excursion during the day if you prefer. We thought the sunset sail was very romantic and loved the views in the evening, but if you can’t make that time, a morning sail would offer pretty views as well.

*****

So there you have it: the most amazing things to do in Old San Juan! Have you been? I would love to hear your thoughts if you have: please comment below to respond.

If you have not yet visited, I hope I have inspired you to plan a trip to Puerto Rico soon! The island is beautiful, and you will love Viejo San Juan.

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Discover the best things to do in Old San Juan! From visiting El Morro to gawking at the colorful facades, this ultimate guide to Old San Juan describes the best sights and experiences, plus where to stay.

Dhara

Dhara's travel interests are eclectic, spanning everything from natural wonders to history, culture, art and architecture. She has visited 22 countries, many more than once, plus almost all 50 states of the USA, and has amassed a hoard of cherished travel moments.

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