Old San Juan

Old San Juan has an unique beauty that can be hardly found somewhere else (perhaps similar to the vibe of Cartagena in Colombia). Although this area doesn’t have beaches, it is famous for its dining, nightlife, and colonial vibe and architecture. 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.

Whether you are visiting for a weekend getaway, a short trip or staying a while, there are aa couple sights that you shouldn’t miss!

Best things to do in Old San Juan

Castillo San Felipe del Morro

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).

Its construction started in 1539, but is wasn’t finalized until 1790, one of the largest fortifications built by Spain in the Caribbean. It is also among the most visited attractions of Puerto Rico, capturing the history of the island with its cannons, casemates and the chapel.

Walking around San Juan

Just Walk around

Old San Juan is little, but it has a lot to see. You could walk the entire town in a couple hours, and it is well worth it! 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!

Mofongo eat local old san juan

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.

dancing salsa cuba

Salsa Dancing

Puerto Ricans are vibrant and friendly people who like to party. 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.

Parque las palomas san juan

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 San Juan

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 Cristobal

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

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


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.

Catedral San Juan Bautista

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.

Old San Juan Tours