The Perfect Weekend in San Juan

Old San Juan may look, at first glance, like a few other charming cities built during the height of Spanish colonialism—Havana or Santo Domingo, for example—but what sets it apart is the extent to which its architectural infrastructure from that era remains visible. It’s the only city that has its original colonial wall almost entirely intact, and both of its principal forts are in excellent condition, remain accessible to the public, and offer panoramic views of the Atlantic Ocean (so bring your camera). Both El Morro and Fuerte San Cristobal are run by the National Park Service; guided tours will leave you with greater knowledge about the era, as well as the forts’ construction and their role in Puerto Rican history. (There are other, smaller forts in and around the capital, next to the Caribe Hilton, and in Luís Muñoz Rivera Park, plus Fort San Juan de la Crúz in the nearby town of Cataño.)

Puerto Rican plazas are laid-back gathering spaces where locals buy snacks, watch shows, play dominoes, and chat with friends. Take a seat on a bench to give your feet a break and soak up some of the everyday comings and goings. At the Plaza de Armas in San Juan, buy the kids traditional treats like sesame-seed lollipops or coconut candies and check out the fountain with the four statues symbolizing the seasons. The Plaza las Delicias in Ponce is made up of two squares divided by a cathedral—one has a statue of journalist and governor Luis Muñoz Marín, while the other is home to the Lions Fountain from the 1939 World Fair.

Dating to 1521, the Cathedral of San Juan Bautista isn’t just one of the oldest buildings in San Juan—it’s the second-oldest cathedral in all of the Americas. Go inside to see the tomb of Spanish explorer Ponce de León, who founded the first settlement on Puerto Rico and in 1509 was named the island’s first governor. The remains of St. Pio, a Roman martyr, can also be seen in the cathedral—the saint’s mummy has been displayed here in a glass box since 1862.

Old San Juan offers historically and culturally significant experiences including a walk through 500-year-old forts, visits to UNESCO sites, historic churches, museums, the second oldest cathedral in the Americas and Ponce de Leon’s mansion. Cobblestone streets and pastel buildings are perfect for exploration during the day and variety of restaurants and shops make for a complementary evening.

Chef Peter Schintler’s San Juan restaurant remains one of the capital’s top fine dining destinations after more than a decade in operation. Marmalade, located in Old San Juan, has allowed Schintler to experiment with international flavors and techniques picked up at previous stints in kitchens around the world, including one at New York’s fabled Le Cirque. While beloved by omnivores and travelers who will jet-set for cocktails, vegetarians especially appreciate Schintler’s menu, which includes a spiced cauliflower meze and hand-rolled black truffle pappardelle. Reservations are definitely recommended.

A recent addition to the Puerto Rican capital’s culinary scene are food hall–style spots where diners can choose among multiple kiosks, or stalls, each featuring a distinct kind of cuisine. Lote 23 is one such spot, located in the working-class neighborhood of Santurce. More than a dozen food entrepreneurs have fare on offer here, from pizza and tacos to bao and burgers. If you just need something to cool yourself off in the tropical heat, there are popsicles and cocktails, too. The alfresco eating area has plenty of picnic tables where you can sit and enjoy whatever you’ve ordered.

Anywhere breakfast is served all day usually scores in my book. At Caficultura in Old San Juan, the food is “farm to table” and is as delicious as the creative menu sounds. In addition to the mostly healthy options, the highlight is the maple syrup made with rum, and coconut milk–dipped french toast topped with coconut shavings. The atmosphere was pretty cool—large black chandeliers hang from large wooden beams, and the picture windows face Plaza Colón outside.


Definitely a cool local place to stop into and grab a coffee or brunch while sightseeing throughout Old San Juan’s historic district.

Feel instantly cool when you slip through the unmarked wooden doors and enter La Factoria. Garden lights hang from the graffiti-covered walls (designed to look artsy-shabby with a stylish restraint), seductive music plays, and the liquor bottles behind the bar are lit from beneath to add to the glow. The flattering amber light in this neighborhood bar invites whispered conversations and lingering glances. La Factoria, which introduced San Juan to the craft cocktail when it opened in 2013, encourages experimentation. Take your time enjoying your drink of choice, but be sure to wander a bit further into the sprawling building where you’ll come upon separate spaces with different moods: a wine bar, a speakeasy, a dance floor.

Cacao beans’ scientific name is theobrama cacao, which translates into “drink of the gods.” Casa Cortés in Old San Juan will truly please any god with its Cortés chocolate concoctions. This welcoming café fuses modern style of its seats and dishes with the antique charm of walls covered in Cortés chocolate molds and a short history of chocolate on a collage of artwork that exudes nostalgia. The menu features mouth-watering items such as a baguette filled with Brie, chocolate, and a hazelnut spread; a blood orange and passion fruit cheesecake topped with a chocolate mousse; and an Argentinian ice wine. I opted for the mallorca (a sweet bread dusted with powdered sugar) stuffed with Ibérico ham, Manchego, chocolate, and a guava spread, accompanied by a European hot chocolate that was to die for. My meal was perfect, but I’m sure everything I didn’t get to taste was just as amazing. That’s what you get when your chocolate comes straight from a nearby farm. While I waited for my food, I watched a video on chocolate production. There’s also a museum (unfortunately, I was unable to see it, but you can bet I’ll be back there next time I come home to my beautiful island) and some products for sale. Make sure to take a little piece of Casa Cortés with you for future indulgences—they advertise one chocolate tablet as being enough for two beverages.

Concalma is the store of designer Matilsha Marxuach, a graduate of the Rhode Island School of Design who creates fair-trade products that are made and sourced locally. Her specialty is chic cloth bags and totes for men and women, and her trendy line offers a variety of sizes, styles and designs. Clothing, bags and jewelry by other designers, both quirky and cutting-edge, are sold here as well.

Old San Juan is known for its atmospheric and historic hotels, but none quite match the Gallery Inn for personality and creativity. Composed of six intertwined town houses, this endlessly fascinating hotel beckons guests to wander through its nine interior gardens and patios, and seven parlors and porticos. Dating to the mid-1700s, the oldest building, La Cueva Del Indio, is located above Old San Juan’s north walls, meaning the views out to sea are the same ones that captivated the conquistadors.

Owner Jan D’Esopo, is a well-known sculptor and her works dot the hotel’s meandering interior, which has enough comforts and homey character to avoid feeling like a museum. Equally unique are the 25 rooms, decorated with everything from silk screens and watercolors to sculptures and paintings. Some even feature elegant, four-poster beds and balconies with views of the ocean. Just don’t expect to watch TV—one, there are no TVs, and two, the views out over the old fortress walls are better than anything on Netflix.