Treasures of Old San Juan, Puerto Rico

Two days of adventure amid 600 years of history in San Juan

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Discover the treasures of old San Juan, Puerto Rico, in 2 days. San Juan is the oldest town in the United States, established in 1508 by Juan Ponce de León. His home, La Casa Blanca, is now a museum and his tomb is in the Catedrál de San Juan Bautista. Old San Juan (Viejo San Juan) is a neighborhood in the capital city of San Juan. This seven-block historic district is by far the most interesting part of the city—the very essence of the island.

Treasures of Old San Juan

Day 1


Old San Juan is guarded by two 500-year-old Spanish forts with a square-mile, seven-block walled city between them. Enter the old city through the Puerta de San Juan, a 16-foot-tall red gate built in the 1600s. Turn right to find San Juan Cathedral (Catedrál de San Juan Bautista) on Calle del Cristo. This 400-year-old church is the resting place of Ponce de Leon, who is buried in a white marble tomb.

When you leave the church, take Calle del Cristo to a black granite totem pole that stands in Plaza del Quinto Centenario, a public square built to commemorate the Quincentennial of the European Discovery of America and Puerto Rico.


Take a five-minute walk back along Calle del Cristo to St. Germain Bistro and Cafe in a pink colonial building at the corner of Calle Cruz and Calle Sol. This eclectic French-inspired eatery has a bit of everything, from sandwiches to vegetarian meals.


Head to El Morro, about a 10-minute walk from St. Germain Bistro and Cafe. Officially known as Castillo San Felipe del Morro, the Spanish-built fortress overlooks the opening into San Juan Bay from the Atlantic Ocean and is the perfect location for defending the island from foes.

When you leave El Morro, amble about the narrow passageways with the intention of getting lost. Every cobblestone street in the old city leads to hidden gems, from unusual shops to secret bars. Enjoy a cup of Puerto Rican coffee or a beer at Cafe Poetico, near Plaza de Armas. Next door, Poetry Passage sells a fantastic selection of products related to music and poetry.


Dinner choices are almost limitless. Foodies may opt for one of the guided tours that include a variety of local favorites.

Find-it-yourself types can head for Marmalade or Trois Cent Onze, both on Calle Fortaleza, for creative fusion dishes.

After Hours

San Juan’s nightlife is among the best in the Caribbean. Drop into LaFactoría, where you’ll find a wine bar, mixology bar, and a dance floor. Calle Cristo has several popular bars, including Don Pablo and El Batey. Nuyorican Cafe bills itself as an “art theater music room.” You won’t find a more popular spot on weekends or late at night.

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Day 2


Fort Cristobal (Castillo San Cristobal) protects the eastern side of Old San Juan. The Spanish began construction in 1634 to defend against an enemy attack by land. El Morro was intended for seaside defense. Wander through leisurely, camera at the ready, and prepare to be awed by the views of the coast. Cristobal is huge, perhaps the largest fortress in the Americas, so allow most of the morning to explore the three levels and outer walls.


El Jibarito is less than a five-minute walk from Fort Cristobal. Try plantain tamales or goat stew for a taste of true Puerto Rican soul food. Another choice is Café BerlÍn, about two minutes from the fort. Sit outside if the weather is nice and enjoy vegetarian or vegan dishes.


Browse the stores in the popular SoFo district, named after South Fortaleza Street. From the Fort Cristobal area,  walk west toward Plaza Colon, turn left at the Brick House bar and follow Calle O’Donnell to Calle Fortaleza, about a three-minute walk. You can amble all the way down this charming cobblestone street to the governor’s mansion, La Fortaleza, near the old gate at Paseo de la Princesa. Along the way, browse through the tempting shops along La Calle, filled with local products, from masks and paintings to gourmet salsa.

Cool off and refresh at Himalaya Ice with a hand-rolled ice cream creation. La Fortaleza is a block down the street and you can visit the elegant mansion from 9:00 am – 4:00 pm on weekdays (free).

If you have the energy, head over to La Casa Blanca (White House), less than a 10-minute walk up Calle del Cristo. This National Historic Monument was built for Ponce de Leon, but he never lived there. The De Leon family occupied the house for more than 200 years and the mansion is now a museum decorated with 16th- to 18th-century antiques.


Book a food tour for your last night. Or try Verde Mesa, a vegetarian restaurant that also serves fish.  For authentic Puerto Rican food, get a table at Deaverdura and order the Puerto Rican Sampler.

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