Old San Juan is the oldest continuously inhabited part of Puerto Rico and is a treasure trove of history, culture, and charm.
With its colorful streets, iconic forts, and stunning architecture, it’s a destination that offers an enriching experience for the whole family.
Whether you’re stopping in Old San Juan on a Caribbean cruise, or just spending a day exploring while on vacation in Puerto Rico, here are 12 things to do in Old San Juan if you only have one day!
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12 Things to do in Old San Juan in One Day
Table of Contents
- 1. Tour Castillo San Felipe del Morro
- 2. Tour Castillo San Cristobal
- 3. Visit Santa Maria Magdalena de Pazzis Cemetery
- 4. Walk through the historic San Juan Gate
- 5. Step inside San Juan Bautista Cathedral
- 6. Take a photo on Calle de la Luna
- 7. Get a frozen hot chocolate from Chocobar Cortés
- 8. Tour La Fortaleza
- 9. Take a photo at Calle Fortaleza
- 10. Get a popsicle from Señor Paleta
- 11. Feed the birds at Pigeon Park
- 12. Wander the streets of Old San Juan
1. Tour Castillo San Felipe del Morro
Start your adventure in Old San Juan by exploring the majestic Castillo San Felipe del Morro.
San Juan is considered the “Gateway to the Caribbean” as it was the first major port that boats would come to when sailing from Europe in the 16th century.
Castillo San Felipe del Morro is one of two stone fortresses in San Juan that was built as a strong defense hold to protect the city against pirates and enemy invaders.
Construction first began in 1539 and was completed in 1790.
Today, visitors can tour the remains of the fortress which has been designated as a UNESCO World Heritage Site.
Spend time exploring the underground tunnels, dungeons, and living quarters.
Then head up to the top where you’ll find cannons, a lighthouse, and sentry boxes where guards once stood watch.
The sweeping views from the top are unmatched.
Your kids will also enjoy participating in the Junior Ranger program, which provides educational activities and a chance to earn a badge.
Castillo San Felipe del Morro is open for self-guided tours year-round from 9 am to 5 pm.
Admission is $10, children under $15 are free. This is also a national historic site so America the Beautiful national park passes are accepted.
The admission price also includes entrance into Castillo San Cristobal.
2. Tour Castillo San Cristobal
Continue your historical journey by visiting Castillo San Cristobal. This second impressive fortification was completed in 1783 and played a significant role in San Juan’s defense.
This is where the first shots of the Spanish American War were fired.
While on a self-guided tour of the fort, be sure to look for the Garita del Diablo or “Devil’s Sentry Box”.
This isolated sentry box is where a Spanish soldier mysteriously disappeared in the middle of the night while on duty.
Castillo San Cristobal also offers interactive exhibits, underground tunnels, and panoramic views.
As you tour around, posted signs will educate visitors about the fort’s construction and the ingenious engineering techniques used to protect the island.
This is also one of the best places to see La Perla, a colorful barrio that was made famous in the Despacito music video.
However, tourists aren’t always welcomed in this neighborhood so it’s best to view it from a distance.
Admission to this fort is included with the purchase of a ticket to Castillo San Felipe del Morro.
For a unique view of the fortresses, La Perla, and Old San Juan, consider taking a sunset sail around the bay.
3. Visit Santa Maria Magdalena de Pazzis Cemetery
Santa María Magdalena de Pazzis Cemetery is one of the prettiest cemeteries in the world, and definitely the prettiest one we’ve ever seen.
The cemetery is tucked between the two fortresses and overlooks the ocean.
Also known as the Old San Juan cemetery, the earliest headstones here date back to 1863 and it is the final resting place for some of Puerto Rico’s most prominent citizens.
The location of the cemetery next to the ocean symbolizes the spirit’s journey as it crosses into the afterlife, which is central to the belief that the Spanish have about the separation of life and death.
The cemetery can be easily viewed from the grounds of del Morro. If you would like to walk around inside the cemetery, you’ll need to enter through a tunnel that can be accessed via Calle Tiburcio Reyes.
4. Walk through the historic San Juan Gate
You’ll notice that much of the original city wall that was erected in the 16th century to protect San Juan is still in tact.
Six guarded city gates were placed around the wall where welcomed visitors could enter the city.
Today, the San Juan Gate is the only one of the original city gates that still remains.
The San Juan Gate dates back to the 1600s and can be found on the western coast of Old San Juan, just south of Castillo del Morro.
As you walk through the gate, you’ll find a beautiful view of the bay and the exterior of the original city wall.
You’ll also find a walking path that leads around outside a portion of the city.
5. Step inside San Juan Bautista Cathedral
A visit to Old San Juan wouldn’t be complete without exploring the San Juan Bautista Cathedral.
This historic church is the oldest cathedral in the US and the second oldest cathedral in the western hemisphere.
It was built in 1521 and is considered the oldest structure in San Juan. It was rebuilt in 1529 after being destroyed by a storm.
You’ll notice that the cathedral sits at the top of the hill directly in front of the San Juan Gate. Visiting dignitaries that arrived at San Juan by boat would walk straight from the gate to the cathedral to thank God for a safe passage.
The road leading up to the cathedral is one of the prettiest streets in Old San Juan with towering shade trees framing the brightly colored colonial buildings.
Once you reach the cathedral, visitors can step inside to marvel at the beautiful architecture, intricate stained glass windows, and religious artifacts.
All are welcome to attend a Sunday mass to experience the vibrant energy and devotion of the local community.
6. Take a photo on Calle de la Luna
Calle de la Luna is perhaps the prettiest street in Old San Juan.
The cobblestone street is lined with a rainbow of brightly colored colonial buildings, and truly captures the essence of Old San Juan.
The best place to snap an iconic shot of this street is just east of San Juan Bautista Cathedral on the corner of Calle de la Luna and Calle San Jose.
The street is pristine and not as crowded as some of the more touristy streets in Old San Juan.
Another photogenic spot is the Black Puerto Rican Flag Mural which can be found painted on an old door of an abandoned building a little further north on Calle San Jose.
7. Get a frozen hot chocolate from Chocobar Cortés
Chocobar Cortés is a family-owned cafe that has been in the Cortés family for four generations.
It was originally established in the Dominican Republic in 1929 and has been serving creations made fresh from Caribbean-grown cacao beans ever since.
They are known for their silky rich hot chocolate, but their frozen hot chocolate sure hits the spot on a hot and muggy Caribbean day.
Chocobar Cortés is also famous for its unique chocolate-infused menu. Try the Chocolate Grilled Cheese Sandwich, a Choco-Chicken Sandwich, or even Caribbean Ceviche with cacao nibs!
If you enjoy trying new foods, consider taking a Flavors of San Juan Food Tour to try some of the best local dishes.
8. Tour La Fortaleza
La Fortaleza, which translates to “the fortress”, was the first fortification built in the walled-in Old City.
It was completed in 1540 to secure the island’s defenses. However, after falling under attack twice, it was converted to the governor’s mansion in 1846.
Today, La Fortaleza is the official residence of the Governor of Puerto Rico and is considered one of the oldest executive mansions in continuous use in the Americas.
While the interior of La Fortaleza is generally closed to the public, the exterior of this impressive structure is worth a visit.
La Fortaleza showcases Spanish colonial architecture and is a symbol of the island’s history and heritage.
Free guided walking tours are available but reservations must be made in advance. See the Office of the Government website for more information.
9. Take a photo at Calle Fortaleza
Calle Fortaleza is one of the oldest streets in Old San Juan and cuts right through the heart of the city before ending at the governor’s mansion.
This narrow cobblestone street has become one of the most photographed spots in Old San Juan.
Several years ago, a colorful canopy of umbrellas was hung above the street as a whimsical art installation. Over the years, the umbrellas have been replaced by other objects, such as a giant Puerto Rican flag. When we visited, pink butterflies were fluttering above the street.
The street is closed to vehicles, and will sometimes be closed to pedestrians if there is an event going on at the governor’s mansion (which was the case while we were visiting).
10. Get a popsicle from Señor Paleta
The best way to cool off while exploring Old San Juan is with a refreshing Spanish-style popsicle from Señor paleta.
A paleta is a tropical frozen treat made from fresh natural fruits and often has a rich and creamy condensed milk base.
There are a wide variety of flavors to choose from at Señor Paleta, all of which are made fresh. Be sure to get your paleta dipped in chocolate and rolled in a topping of your choice.
The shop is small so expect a wait, especially in the summer months, but it is worth it!
11. Feed the birds at Pigeon Park
Parque de las Palomas, or “Pigeon Park”, is a unique stop in Old San Juan.
It is located just down the road from La Fortaleza and adjacent to the historic Capilla del Cristo, a small chapel and museum.
Pigeon Park is a sanctuary for hundreds of pigeons. If you have a fear of birds, this is not the place for you!
If you don’t mind being surrounded by pigeons, then you can purchase a bag of bird seeds for $2 and the birds will flock to you.
My kids had the best time feeding the birds and it was a highlight of Old San Juan for them. Just be sure to use the provided hand sanitizer afterward.
The park itself is a pretty little pocket in the city, with large mature trees and views overlooking the ocean.
12. Wander the streets of Old San Juan
Sometimes the best way to explore a city is just by wandering the streets with no agenda in mind.
Old San Juan is a very walkable city and the perfect place to aimlessly wander as there is always something to see.
One of the best ways to explore the city is with a guided walking tour. The tours are inexpensive and your knowledgeable guide will share some great insights into the history of Old San Juan.
It is possible to explore all of Old San Juan on foot, you do not need a car.
If you do have a car, parking is limited in the city but there is plenty of parking available at the nearby La Puntilla parking lot. The rate is only $3 per day.
A free trolley and garitas (golf carts) are also available to transport visitors around to the tourist sites. Click the link for the schedule and more information.
After parking, head out to explore the city streets.
Stop in a local shop, visit one of the city squares, venture into the side streets and alleyways, and sample some local Puerto Rican food.
Old San Juan is filled with so many photogenic cobblestone streets just bursting with color and character.
Calle de San Francisco is one of the main tourist streets running through Old San Juan. It is lined with local shops, cafes, restaurants, and galleries. This is the best place to go souvenir shopping.
This is also where you’ll find Cafetería Mallorca, a casual bakery and diner with the best traditional Mallorca sandwiches.
The flakey pastry sandwiches are made with ham and cheese, and dusted with powdered sugar.
In addition to the Mallorca sandwiches, they have an extensive breakfast and lunch menu as well as a variety of freshly baked pastries.
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Old San Juan is a captivating destination that combines history, culture, and culinary delights.
From exploring imposing forts to strolling through picturesque neighborhoods, there’s no shortage of things to do in Old San Juan!
And if you would like more recommendations for your time in Puerto Rico, check out our Ambitious 7-Day Puerto Rico Itinerary!
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