25 Top Things To Do In Old San Juan Puerto Rico
Discover the best things to do in San Juan, Puerto Rico with expert tips from locals. From historic landmarks and scenic walks to vibrant plazas and delicious local treats.
Old San Juan, Puerto Rico, is a destination that effortlessly blends history, culture, and vibrant modern life.
The city was founded in 1521 and is the oldest city under the United States flag and a UNESCO World Heritage site.
This historic city was originally known as “Puerto Rico,” meaning “rich port,” while the island itself was called San Juan Bautista.
Over time, the names switched, with the city adopting the name San Juan.
As the second-oldest European-established city in the Americas, Old San Juan is characterized by its colorful colonial architecture, cobblestone streets, and towering city walls.
Over the centuries, Old San Juan became a vibrant blend of Spanish, African, and indigenous influences, which can be seen in its architecture, music, and food.
Today, it remains a lively district where visitors can walk through over 500 years of history while enjoying modern-day Puerto Rican culture.
Whether you’re planning your first trip, stopping by on a cruise, or looking to discover more about this beautiful city, this guide highlights the must-visit spots and hidden gems in Old San Juan.
1. Explore the Iconic Castillo San Felipe del Morro
One of the top things to do in Old San Juan is visit El Morro.
El Morro, officially known as Castillo San Felipe del Morro, is a massive 16th-century fortress built by the Spanish to defend San Juan from naval attacks.
The fortress was expanded multiple times, making it a key military stronghold in the Caribbean.
The U.S. military used it during World War II to guard against German submarines.
With its towering walls, sweeping ocean views, and historic significance, it’s one of the most iconic landmarks in Puerto Rico.
As you walk through its massive walls and winding pathways, you’ll get a glimpse into Puerto Rico’s military past.
Highlights:
- Enjoy breathtaking views of San Juan Bay from multiple lookout points.
- Explore underground tunnels and climb the iconic lighthouse.
- Explore the cannon platforms that defended against sea attacks.
- Visit the barracks where soldiers lived and slept.
- Fly a kite or enjoy a picnic on the large green fields surrounding the fort.
2. Visit the Majestic Castillo San Cristóbal
Close to El Morro, Castillo San Cristóbal is another fortress that guarded the city from land attacks.
El Castillo de San Cristóbal was built by the Spanish in 1783 to protect San Juan from land attacks.
It’s the largest fort built by the Spanish in the New World and offers a deep dive into military architecture.
Over time, it successfully defended the city against invaders, including a major British assault in 1797.
Today, you can explore its tunnels, dungeons, and military structures while learning about its role in Puerto Rico’s history.
Things to Do:
- Visit the dungeon and see graffiti left by prisoners.
- Climb to the top for panoramic views of Old San Juan.
- Explore the cannon batteries that defended the city.
- Explore the underground chambers used for storage and defense.
- Learn about Old San Juan’s defenses through the educational exhibits
3. Parque de las Palomas
This activity can be a hit or miss, depending on whether you like pigeons or not.
El Parque de las Palomas, which translates to Pigeon Park, gets its name from the flocks of pigeons that gather here.
The park has stunning views of San Juan Bay, and local families often bring their kids to feed the pigeons.
Yes, that’s right. We buy bird food from local vendors, hold it in our hands, and wait for the pigeons to come and eat.
Important: Bring an extra shirt and wipes to clean up afterward. I’ve had to buy a new shirt before because pigeons have pooped on me. It’s part of the fun.
4. Stroll Along El Paseo de la Princesa
El Paseo de la Princesa is a scenic promenade along Old San Juan’s city walls, with beautiful views of San Juan Bay.
Designed in the early 20th century, this beautifully landscaped walkway features vibrant sculptures and historical monuments, including the iconic Raíces Fountain.
The Raíces Fountain celebrates Puerto Rican heritage with its striking sculpture of roots and figures.
On weekends, local artisans sell traditional Puerto Rican art, local food, and more.
As you stroll along El Paseo de la Princesa, you’ll see the massive fortifications of El Morro.
The walkway takes you behind El Morro, alongside San Juan Bay, which attracts many morning runners and joggers.
Enter Old San Juan through the Puerta de San Juan, a grand city gate built in the 16th century.
This historic entrance once served as the main gateway to the fortified city, offering a dramatic entry into the heart of Old San Juan.
5. Try a Refreshing Piragüa
While walking around it can get hot at any time of the year.
Cool off with a piragüa, a popular Puerto Rican shaved ice treat.
These icy delights come in various tropical flavors, like mango, coconut, or tamarind.
You’ll find them at small stands throughout Old San Juan, especially in busy areas.
6. Plaza de Armas
Plaza de Armas is a lively square in Old San Juan that draws locals and visitors alike.
It features charming colonial architecture and provides a perfect spot to relax and people-watch.
You’ll find colorful buildings and historic landmarks around the square, reflecting the city’s rich history.
The plaza often hosts events and gatherings, making it a vibrant place to experience the local culture.
Must-See:
- The City Hall, an impressive building with neoclassical architecture
- Festivals and events are often hosted here, so you might catch some live music or dance performances
7. Historic San Juan Cathedral
A visit to Old San Juan is incomplete without stopping by the Catedral de San Juan Bautista.
The Cathedral of San Juan Bautista, built in the 16th century, stands as one of the oldest churches in the Americas.
It played a central role in San Juan’s religious life and served as the site of significant historical events.
The cathedral is famous for its Gothic architecture and as the final resting place of Juan Ponce de León, the renowned explorer of the Fountain of Youth who was the first Spanish governor of Puerto Rico.
Today, the Cathedral still hosts mass and is a popular choice for weddings.
Don’t Miss:
- The beautiful stained glass windows
- The tomb of Ponce de León inside the cathedral
8. Admire San José Church
Dating back to the early 1500s, Iglesia de San José is one of the oldest churches in the Americas.
This historic church was built in the early 16th century under the Spanish rule.
It’s one of the few surviving examples of Spanish Gothic architecture in the Western Hemisphere.
The church has been under renovation for the last 20 years and it has finally opened to the public. The church experienced severe deterioration and structural damage problems.
The church’s exterior is simple yet elegant, with its whitewashed walls and distinctive bell tower.
Inside, you’ll find a serene and contemplative space, with a modest but charming interior.
9. Discover Capilla del Cristo
A small chapel with a big legend, Capilla del Cristo was built in the 18th century and sits at the end of Calle del Cristo.
According to legend, a rider miraculously survived a fall from the nearby city wall, and the chapel was built in gratitude.
Capilla del Cristo, built in 1753, is a small yet significant chapel in Old San Juan.
It originally served as a place of worship for sailors and travelers seeking protection.
The chapel is known for its simple but elegant design and its role in local traditions.
Over the years, it has become a cherished historical site and a symbol of faith for the community.
10. Explore Cuartel de Ballajá
Cuartel de Ballajá, built in the early 19th century, originally served as a military barracks for Spanish troops in San Juan.
Its impressive neoclassical architecture housed soldiers and their families.
After serving various military purposes, the building now has a cultural institution, a museum, and educational events
It’s a great stop for those interested in learning about Puerto Rico’s cultural history.
Must-Do:
- Visit the Museum of the Americas located inside
- The building’s open courtyard is perfect for taking photos
11. El Totem Sculpture
This modern sculpture known as El Totem is located in Plaza del Quinto Centenario next to el Cuartel de Ballajá.
It was created by Puerto Rican artist Francisco Zúñiga in 1986.
This modern totem represents the island’s indigenous heritage and cultural roots.
It stands as a prominent symbol in the city, celebrating Puerto Rican identity and artistic expression.
Many Puerto Ricans use it as a meeting point during festivals and events.
12. La Fortaleza and the Umbrella Street
A visit to La Fortaleza is essential when looking for things to do in Old San Juan, Puerto Rico.
La Fortaleza, built in 1540, is the oldest governor’s mansion in continuous use in the Western Hemisphere.
Originally constructed as a fort to defend San Juan, it later became the residence of Puerto Rico’s governors.
La Fortaleza features a blend of military fortification and colonial architecture, with its thick stone walls, arched doorways, and elegant courtyards.
Today, La Fortaleza serves as the official residence and office of the governor, showcasing centuries of history and architecture.
Don’t forget to walk along Fortaleza Street, where colorful umbrellas create a stunning canopy over the street.
This spot is perfect for an Instagram photo! Arrive early to avoid the crowds.
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13. Casa Blanca Museum
Casa Blanca Museum, built in 1521, originally served as the home of Juan Ponce de León, the island’s first governor.
The historic house features Spanish colonial architecture and offers a glimpse into 16th-century life in Puerto Rico.
Today, it operates as a museum, showcasing artifacts and exhibits related to the island’s early history and Ponce de León’s legacy.
The gardens at Casa Blanca Museum are beautifully landscaped with lush tropical plants and historic features, providing a serene escape and a glimpse into the colonial era.
14. Felisa Rincón de Gautier Museum
Museo Felisa Rincón de Gautier, established in 1990, honors Puerto Rico’s first female mayor, Felisa Rincón de Gautier.
The museum is housed in her former residence and showcases her contributions to Puerto Rican politics and society.
Visitors can explore exhibits featuring memorabilia, photographs, and documents that highlight Rincón de Gautier’s pioneering role in local government and her impact on the community.
The museum offers valuable insight into her legacy and the progress of women in Puerto Rican politics.
15. Antiguo Casino de Puerto Rico
Antiguo Casino de Puerto Rico, built in 1917, originally served as a social club for San Juan’s elite.
Its grand architecture and opulent interiors made it a central gathering place for high society events and cultural activities.
Today, the building functions as a cultural center, hosting weddings, art exhibitions, concerts, and other public events.
Its historical charm and significance continue to attract visitors who appreciate its role in Puerto Rican cultural history.
16. Experience a Show at Teatro Tapia
For culture lovers, catching a performance at Teatro Tapia is one of the best things to do in Old San Juan, Puerto Rico.
Teatro Tapia, inaugurated in 1824, is one of the oldest theaters in Puerto Rico.
It originally served as a venue for operas, plays, and concerts, reflecting the city’s rich cultural life.
Today, Teatro Tapia continues to host performances and cultural events, preserving its historic charm and offering a glimpse into the island’s artistic heritage.
The theater’s classic architecture and interior design make it a cherished landmark in San Juan.
17. Eat, Drink, and Dance at Callejón de la Tanca
Callejón de la Tanca is a vibrant alley in Old San Juan known for its lively atmosphere and local charm.
The street features colorful buildings, bustling shops, and cozy restaurants where visitors can enjoy Puerto Rican cuisine and live music.
Local musicians often perform here, creating a festive environment that captures the essence of San Juan’s cultural scene.
Walking through Callejón de la Tanca offers an authentic experience of the city’s vibrant community.
18. Santa María Magdalena de Pazzis Cementary
Located next to El Morro, this picturesque cemetery is the final resting place for many notable Puerto Ricans.
Established in 1863, it features elaborate mausoleums and impressive sculptures that reflect Puerto Rican history and architecture.
Puerto Rican notable figures buried here include:
- Pedro Albizu Campos – nationalist leader and politician
- Jose Celso Barbosa – founder of the Puerto Rican statehood movement
- José de Diego – Poet, lawyer, and liberal politician
- Manuel Fernandez Junos – writer of the Puerto Rican national anthem
- Rafael Hernández – composer and musician
- Lolita Lebrón – nationalist leader
- Rafel Tufiño – painter and graphic artist
Its location, overlooking the ocean, makes it a serene and beautiful spot to visit.
19. Puerta de San Juan
La Puerta de San Juan, built in 1539, is one of the original gates of the old city walls in San Juan.
This historic entrance once served as the main entry point to the fortified city and played a key role in its defense.
Today, La Puerta de San Juan stands as a significant historical landmark, offering a glimpse into the city’s past and a grand gateway into Old San Juan.
Its sturdy, time-worn structure highlights the fortifications that once protected the city from invaders.
20. Find La Casa Más Estrecha
La Casa Más Estrecha, known as the narrowest house in Old San Juan, was built in the 19th century.
It stands out due to its extremely narrow façade, measuring only about 5 feet wide.
Today, La Casa Más Estrecha is a charming example of the city’s unique architectural heritage.
Visitors often admire its quirky appearance and learn about its history as part of Old San Juan’s eclectic mix of buildings.
21. Discover Callejón de la Puerta con la Bandera
A hidden gem in Old San Juan, this alley features a large Puerto Rican flag painted on a door.
Callejón de la Puerta con la Bandera is an alley in Old San Juan, famous for its vibrant Puerto Rican flag mural.
This narrow street features lively artwork and provides a picturesque setting for photos.
Visitors flock to Callejón de la Puerta con la Bandera to capture the vivid colors and cultural spirit of Puerto Rico.
The mural and the surrounding area offer a glimpse into the island’s artistic and patriotic pride.
22. See the Puerta Bandera Blanca y Negra
The Puerta Bandera Blanca y Negra, located on Calle San José, is another mural of the Puerto Rican flag painted in black and white, symbolizing resilience and protest.
Before 2016, the flag displayed its original colors, but on July 4th, local artists painted it black in protest of a law the Senate was about to approve.
Many visitors and locales alike flock to the Flag Door to take pictures.
23. Cool Off with Limbers de San Juan
Another way to cool off in Old San Juan is by eating a limber.
A limber is a refreshing Puerto Rican frozen treat made with fruit juice and freezing it overnight in a plastic cup, similar to a popsicle.
The most famous spot to get a limber is Limbers de San Juan, a house located on Monja Street near the Puerta de San Juan.
Years ago, you would walk up to the “limber house” and shout “Limber!” to get the owner’s attention. She would then open a window and sell you a limber for $0.50.
Those were the good old days! Now you just need to ring the bell.
24. Bar Hop Along Calle San Sebastián
Calle San Sebastián is famous for its lively nightlife, particularly its bar scene.
Whether you want to sip a cocktail or dance to salsa, this is the street to be on after dark.
Must-visit bars:
- La Factoría – Known for its creative cocktails and lively atmosphere, this bar often features live salsa music and has 5 different rooms with unique atmospheres.
- El Batey – A historic dive bar with a laid-back vibe, famous for its graffiti-covered walls and strong drinks.
- Barrachina – Renowned for its classic piña coladas, this bar offers a vibrant setting and traditional Puerto Rican food.
- La Taberna Lúpulo – A popular spot for craft beers, featuring a wide selection of local and international brews.
- El Jibarito – A lively spot offering great cocktails, traditional Puerto Rican dishes, and a fun, casual atmosphere.
- Nono’s – Known for its relaxed vibe and excellent cocktails, Nono’s is a favorite for both locals and tourists.
- Café del Angel – Offers a cozy atmosphere with a variety of drinks and a selection of small plates.
- La Cubanita – A lively bar with a Cuban flair, known for its cocktails and vibrant nightlife.
- El Ocho – Offers a relaxed environment with a great selection of drinks and a casual, friendly atmosphere.
- La Terraza – Known for its rooftop views, La Terraza offers a great spot for enjoying drinks and soaking in the San Juan skyline.
25. Parking in Old San Juan
Parking can be tricky in Old San Juan if you have a rental car.
The law prohibits parking on streets reserved for residents only, and violators face a $250 fine. If the car remains parked after two hours, an additional $50 fine applies.
The city may also tow your car if you break this law.
As non-Old San Juan residents, we always use parking garages to avoid fines, and the costs are relatively low.
Recommended Parking Garages:
- Doña Fela Multi-story – This is our go-to parking garage. It offers safety, affordability, a flat nightly rate, and a convenient location.
- Covadonga Multi-story – This is another good, budget-friendly option, though it requires a bit of walking. If Doña Fela is full this is a great option.
- Ballajá Underground Multi-story – This garage is ideal for visiting Calle San Sebastián or El Morro, providing easy access to these areas.
- La Puntilla – This outdoor parking lot is affordable and located right in front of Paseo de la Princesa.
- Paseo Portuario Multi-story– Located next to Doña Fela, this garage is the most expensive of the five options. However, it remains affordable compared to parking prices in major U.S. cities.
Old San Juan Top Picks
Old San Juan is a treasure trove of history, culture, and charm.
From its stunning fortresses and historic churches to its lively streets and delicious treats, there are countless things to do in Old San Juan, Puerto Rico.
Whether you’re planning your first visit or looking to explore more of this enchanting city, the experiences here will leave you with unforgettable memories.
Make sure to take your time, explore the hidden corners, and soak in the vibrant atmosphere that makes Old San Juan so special.
