10 Favorite Experiences in Old San Juan

The oldest European-established settlement under U.S. jurisdiction, Old San Juan is a colorful colonial town that echoes with centuries of history. Culturally and geographically, Old San Juan is quite distinct from the rest of the city. Viejo San Juan – as the locals refer to it--- sits on a tiny island on the north coast of Puerto Rico and is connected to the mainland of Puerto Rico by three bridges. A lively and walkable town, it oozes with energy and joie de vivre, its narrow cobblestone-lined streets literally pulsating with the dynamic rhythm of the Caribbean. Its restaurants offer a one-of-a-kind gastronomic experiences; its colonial architecture is some of the finest in the region. Want to experience it yourself? Try the following 10 experiences:

You can’t travel to Old San Juan without visiting the sister forts of El Morro and San Cristóbal. The two forts stand guard on the coast of Old San Juan as a reminder of century-long Spanish rule in the West Indies. Nicknamed Gibraltar of the Caribbean, San Juan was the key frontier outpost of the Viceroyalty of New Spain. El Morro and San Cristobál glower across the Atlantic at any enemies – protecting the old town from invasion. The aggressive El Morro is believed to be the oldest Spanish fort in the Americas and the monumental Fuerte San Cristobál is one of the largest military installations ever built by the Spanish in the New World. The forts are connected by Calle Norzagaray, and although you can go from one fort to the other by taking a trolley, a walk along Norzagaray, by the pastel-colored houses of La Perla (stop by some of the museums along the way if you have time) is the more rewarding way to go. Cost: $3 each. Get the combo ticket to both of the forts for just $5.

On any given weekend, you’ll see countless colorful chiringas – the Spanish word for kites---of different shapes, dotting the sky of Old San Juan. The coastal breeze and the wide-open space make the park a perfect location for kite flying. You can choose to join the locals by flying a chiringa or spend a lazy afternoon picnicking. El Morro Park is also the place where locals play béisbol – Puerto Rico’s national sport, and where tourists catch a glimpse of the picturesque (not to mention historic) San Juan cemetery. Cost: You can get a chiringa and the string for less than $5 from one of the street vendors around the park (or you can always bring your own).

Every Saturday, the courtyard of Museo de San Juan is transformed into a community farmers market, where locals and visitors shop for the freshest local produce or purchase traditional handicrafts (or both). Stop by the market to tuck in an affordable and delicious brunch prepared from organic ingredients and served by friendly chefs. The market has a bountiful selection of vegetarian foods, which is rare to find on the island. Also on sale: flowers, aromatic soaps, and even composting worms used in vermiculture. Cost: Spend as much as you will!

Paseo del Morro is a trail following the masonry wall that surrounds the old city. The waterfront walkway connects San Juan Gate with El Morro, although the path does not provide access to the fort. The best time to take a stroll along this National Recreational Trail is at the end of the day as the sun sets over the bay and Cataño starts to light up. You will be sharing the trail with Old San Juan’s most conspicuous occupants: feral cats. Hundreds of them roam the street of and the Paseo del Morro is the place where they stretch and sunbathe. Cost: Free.

The second oldest cathedral in the Western Hemisphere is the prime example of authentic and rare New World architecture. It is located up the hill from San Juan Gate and the cathedral was the place where voyagers thanked God as soon as they got off the boat. It now it serves as the seat of the Archdiocese of Puerto Rico. Besides its ecclesiastical functions, Cathedral of San Juan Bautista is the final resting place of two famous, historical figures. Juan Ponce de Leon, founder of the first settlement in Puerto Rico and the island’s first governor, is entombed inside a marble casing inside the building. The cathedral also holds the relic of Saint Pius, a first century Christian martyr, inside a glass case so visitors are able to see his wax-coated remains. Cost: Free.

At the end of Calle del Cristo, there is a quaint little park filled with hundreds of palomas (the Spanish word for pigeons). Parque de las Palomas is a shady area with a great vista where you can enjoy the beautiful views of San Juan. Little kids love running around this park while feeding the gentle pigeons (and you should, too). When you choose to feed these birds, they will go at you fast (and one or two might try to climb onto you), but it’s a great fun for everybody and a wonderful photo opportunity. Don’t forget to cover your head! Although it is considered good luck by the locals, you don’t want to get anointed with bird droppings. Bringing hand sanitizer is also a good idea. Right next to the park is Capillo del Cristo, a well-preserved chapel built to celebrate a local miracle. Cost: You can buy a bag of peas or corn for $1.

Cuartel de Ballajá, a military barrack that houses the Museo de las Americas, is a completely different place at night. The building glows in colorful lights and the songs of the coquís ,Puerto Rican endemic frogs, fill the air. Every Thursday and Friday night, people come to the plaza to see a 17 minute-long 3D projection presentation entitled Puerto Rico: La Isla del Encanto. It’s a feast for the senses, a creative and spectacular combination of light and sound. Employing an intricate filmmaking technique called ultra HD 3D projection mapping, realistic-looking scenes are projected onto the far wall of the barrack. The show chronicles the long history of Puerto Rico from the Pre-Columbian era, as well as depicting the lively culture of Puerto Rico. The event also includes images of famous Puerto Ricans (including politicians, activists, actors, athletes, artists, and beauty pageant winners). There are two versions of the show: one in Spanish and one in English, shown alternately throughout the night starting at 7pm. Cost: Free.

Puerto Rican cuisine has a uniquely distinctive taste, a flavorful blend of Taíno, Spanish, African, and American influences. Locals refer to their cuisine as “cucina criolla” (creole cuisine) and many dishes involve deep-frying. Plantains can be considered as a staple for Puerto Rican people. Mofongo, the signature dish of Puerto Rico, is made from mashing fried green plantains in a pilón, a wooden mortar. The vegetables are served with fried meat as well as soup. The dish is a must-try for every visitor, and it can be found in virtually everywhere across the island – from little food stalls to five-star restaurants. Other than mofongo, you should also try tostones (fried plantain slices) and amarillos (sweet fried plantains; known as maduros in Cuba). As for the drinks, Puerto Ricans are proud of their rums, and the commonwealth boasts the top-selling rum in the world. Unlike in the fifty states, legal drinking age on the island is 18. Cost: Varies by restaurant.

The name translates to “The Promenade of the Princess”, and it is a beautiful pathway along the southern tip of Old San Juan decorated with constantly-changing displays and a rather European atmosphere. The Paseo de la Princesa also provides great views to the Atlantic Ocean and San Juan Bay. After the night falls, artisans and food vendors line the promenade, tempting strollers to peruse their artworks, nibble Puerto Rican snacks (such as alcapurrias and bacalaítos), and quench their thirst with piña colada or piragua. The walkway culminates at the glorious fountain of Raíces, which depicts the symbolism of Puerto Rican history. Cost: Free, but spending a few bucks at one of those street vendors is highly recommended.

The night is always lively in Old San Juan. Entertainment comes in every variety imaginable: casinos, bars, performing art scene, you name it. However, Old San Juan’s plazas are hard to beat. Musicians of all sorts gather and put on impromptu concerts there. If you’re lucky, you’ll also see Latin dancers moving to the rhythm of salsa, merengue, or bachata. In the Plaza de Colón, where a statue of Columbus stands tall atop a pillar. Adjacent to Iglesia de San José is Plaza de San José, where street musicians and young local performers spend their weekend nights entertaining the local crowd. Like the people and the food, Puerto Rican music is an eclectic mix shaped by the dynamic history of cultural assimilation. Cost: Free.