Old San Juan

Puerto Rico’s historic colonial district with colorful streets and centuries-old landmarks.

Old San Juan is the historic heart of Puerto Rico’s capital, known for its cobblestone streets, colorful Spanish colonial buildings, and impressive fortifications. The district is one of the oldest European settlements in the Americas and has been designated a UNESCO World Heritage Site.

Although this area doesn’t have beaches, it is famous for its dining, nightlife, and colonial vibe and architecture. It is compact enough to explore on foot and includes landmarks, museums, shops, and restaurants, making it one of the island’s most popular destinations.

It was founded in 1521 by Spanish settlers, nowadays featuring history with music, vibrant colors and friendly locals. It is the second oldest city established in America, and one of the most historically significant destination in the Caribbean.

History

Founded in 1521, Old San Juan quickly became a key stronghold for Spain in the Caribbean. Its strategic location at the entrance of San Juan Bay made it an essential port for trade and defense. The city was heavily fortified with walls and castles, including Castillo San Felipe del Morro and Castillo San Cristóbal, to protect against European rivals and pirates.

Over the centuries, Old San Juan developed into a vibrant colonial town, with churches, plazas, and residences that remain preserved today. The district’s layout and architecture reflect centuries of Spanish influence, combined with more recent U.S. governance since 1898.

What to See and Do

Visit Castillo San Felipe del Morro

Overlooking the San Juan Bay, El Morro is one of Puerto Rico’s most famous fortresses, a six-level military outpost used by Spain and later United States during the colonization era of Puerto Rico. El Morro was the second fortress built in the island (after “La Fortaleza, which nowadays serves as the governor’s home).

Walk around

Old San Juan is little, but it has a lot to see. You could walk the entire town in a couple hours. The city is filled with colorful restored colonial buildings, charming cobblestone streets small shops and beautiful views of the Bay. It is also a great place to take some pictures!

Eat Local

Puerto rican food is very tasty, and some of the best can be found in San Juan.

One of my favorite places to go to is Barrachina, a 40 year old restaurant that features all the puerto rican classics like mofongo, alcapurrias and habichuelas, in addition to being the birthplace of the world famous Piña Colada, where don Ramón Portas Mingot first made the drink in 1963.

Salsa Dancing

Old San Juan is home to many clubs and bars where you can enjoy a drink, some live music and good dancing, but my favorite perhaps is “La Factoria”. Chosen as one of “The world’s 50 best bars”, tropical cocktails, local flavors, secret passages, live music and 6 different bars can be found in here, enticing guests to dance the night away.

Visit "Parque de las Palomas"

Located on the top of the city wall on the southern end of Calle del Cristo, “Parque de las Palomas” or “Pigeon Square” in english, is a small cobblestone square filled with pigeons, (hundreds of them) that overlooks the Bay of San Juan, offering great views and a funny experience with the birds, which you can feed or chase.

Señor Paleta

Located in the heart of Old San Juan, Señor Paleta is a little and cute popsicle shop, offering a great variety of tropical and classic gelatos and sorbets (it has so many flavors it is very hard to choose one!) to die for. A must if you are visiting San Juan.

Fort San Cristóbal

Located in Old San Juan and with over 27 acres of land, the “Castillo San Cristobal” is the largest and best preserved fortress built by the Spanish in America, created to protect San Juan against land based attacks.

Inside you can find a museum about the history of the fortress, tunnel systems, military uniforms, garitas, cannonballs, living quarters, outworks and a chapel.

Paseo La Princesa

Paseo la Princesa is one of the most beautiful promenades in San Juan, offering great sightseeing of the city, the bay and encountering important landmarks on its way like the historic Puerta de San Juan (the gate used by the Spanish to guard the city), beautiful sculptures and a great deal of food and culture.

Shopping

Old San juan has a lot of artisan and souvenir stores, as well as clothing boutiques and local products like cigars, guayaberas and panama hats. It offers unique products that you will hardly find somewhere else, while allowing shoppers to enjoy its bright colors and beautiful architecture on the way.

Cathedral San Juan Bautista

The Cathedral is an icon of the city, with its beautiful and medieval architecture, built in 1540, it is the second oldest Cathedral in the Western Hemisphere.

Getting Around San Juan

On Foot: Old San Juan is very walkable, with most main attractions located within a few blocks of each other. Comfortable shoes are essential because of uneven cobblestones.
Public Transport: Buses operate in the metro area, but routes and schedules can be limited. They work better for residents than visitors.
Rideshare & Taxis: Uber operates in San Juan and is often the easiest way to move between neighborhoods like Condado, Miramar, and Santurce. Taxis are also available but less common outside busy spots.
Car Rental: Renting a car is useful if you plan day trips outside San Juan (like El Yunque or beaches farther east). Within Old San Juan, parking can be difficult.

When to Visit & Weather

Like much of Puerto Rico, San Juan has a tropical climate. Expect warm temperatures year-round with frequent rain showers in summer months. Hurricane season runs June through November. Shoulder seasons (spring and early fall) may offer fewer crowds and milder rain risk.

Tips for Visiting

Wear comfortable shoes, as the cobblestone streets can be uneven.
Start early in the day to avoid crowds and midday heat.
Many attractions, including the forts, are managed by the U.S. National Park Service and may require an entrance fee.
If visiting during weekends or holidays, expect larger crowds.

More things to do in Puerto Rico

Wondering what to wear or when to go? Check our Puerto Rico travel guide to discover more!

Check Puerto Rico Travel Guide

Are you ready to start discovering San Juan?

If you prefer organized experiences, tours can be a good way to explore San Juan and beyond without handling logistics. This is the list of our recommended tours

Are you ready to start discovering San Juan?

If you prefer organized experiences, tours can be a good way to explore San Juan and beyond without handling logistics. This is the list of our recommended tours