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.
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.
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.
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.
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.
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.
#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.
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.
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.
With their many ramparts, passageways, and sentry boxes, the forts of Old San Juan are fun places to explore: one of the best things to do with kids in Puerto Rico!
#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.
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.
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.
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.
#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.
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.
#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.
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.
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!
#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.
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.
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.
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.
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!
#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.
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.
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!
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.
#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.
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.
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.
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.”
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!
#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!
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.
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.
#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!
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
#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.
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.
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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