Top Things to Do in Old San Juan

With its pastel-colored streets, centuries-old forts, and lively plazas, Old San Juan feels like stepping into another world. The walled city is compact and walkable, making it easy to soak in history, food, and culture in just a day or two. Whether you’re visiting on a cruise stop or staying longer in Puerto Rico, here are the top things to do in Old San Juan.

1. Walk the Cobblestone Streets

Simply wandering the streets is an experience in itself. Blue cobblestones, Spanish colonial buildings, and colorful facades make Old San Juan one of the most photogenic cities in the Caribbean. Don’t forget to peek down side streets for hidden courtyards and murals.

If you’d like to turn your walk into more of an adventure, you can try a self-guided scavenger hunt experience like Tour in a Box: San Juan. It blends riddles, history, and local tips while guiding you through the city’s highlights.

2. Explore Castillo San Felipe del Morro

“El Morro” is the city’s most famous landmark. This 16th-century fort was built to guard San Juan Bay and is now a UNESCO World Heritage Site. Climb the ramparts for sweeping ocean views, stroll the grassy lawn, and imagine the battles that once took place here.

3. Visit Castillo San Cristóbal

Just a short walk from El Morro, this massive fort is the largest Spanish fortification in the Americas. Its tunnels, dungeons, and lookout points give a fascinating glimpse into San Juan’s military past. Together, the two forts are some of the most impressive historic sites in the Caribbean.

4. Relax in Plaza de Armas and Plaza Colón

Plazas are the heart of Old San Juan. Plaza de Armas is lined with cafes and is a great spot for people-watching. Plaza Colón, with its statue of Christopher Columbus, is often filled with local vendors and street performers.

5. Step Inside San Juan Cathedral

Catedral de San Juan Bautista is one of the oldest cathedrals in the Americas, dating back to 1540. The church is beautifully preserved and is the final resting place of Spanish explorer Juan Ponce de León.

6. Shop and Stroll Along Calle Fortaleza

Calle Fortaleza is a lively street filled with boutiques, souvenir shops, and restaurants. At one end, you’ll often see colorful umbrella or flag installations hanging above the street, perfect for photos.

7. Try Local Food and Drinks

No visit is complete without sampling Puerto Rican cuisine. Order mofongo (mashed plantains with savory fillings), sip a piña colada where the drink was invented, and try local favorites like empanadillas and alcapurrias from street vendors. For dessert, look out for piraguas, refreshing shaved ice with tropical syrups.

8. Visit La Fortaleza

The governor’s mansion, known as La Fortaleza, is the oldest executive residence still in use in the Western Hemisphere. Guided tours are available on weekdays and showcase its history and architecture.

9. Walk the Paseo de la Princesa

This scenic promenade runs along the old city walls and is lined with sculptures, food kiosks, and local artisans. It leads to the iconic Raíces Fountain, a great spot to catch the sunset over San Juan Bay.

10. Take in the Views at Puerta de San Juan

The San Juan Gate, once the main entrance to the city, is a striking reminder of the city’s colonial past. Walking through the gate brings you right onto the waterfront with views of the bay.

Bonus: Try a Self-Guided Adventure

Beyond sightseeing, you can immerse yourself in Old San Juan with Tour in a Box, a digital scavenger hunt that leads you to these historic spots while challenging you with riddles and stories of pirates, plazas, and hidden gems.

Final Tips for Visiting

• Old San Juan is very walkable but the cobblestones can be uneven, so wear comfortable shoes.

• Start early to avoid the heat and crowds, especially if you’re visiting from a cruise ship.

• If you have limited time, focus on El Morro, the Cathedral, and a stroll through the plazas for a perfect introduction.

Old San Juan is a city that blends history, culture, and Caribbean charm. Whether you’re there for a few hours or a few days, it’s a place that will stay with you long after you leave.