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Lose Your Heart in San Juan

San Juan

Hotel El Convento, San Juan

There is no doubt that San Juan, Puerto Rico, lives up to the dream tropical island vacation. Sitting in the middle of the aquamarine Caribbean—only three hours and change by air from the U.S. East Coast—the island boasts white sand beaches, blue cobblestones, unique Criollo cuisine and a nightlife that swings to the beat of the island’s world-dominating cultural export: reggaetón.

Puerto Rico can absolutely excel at a simple shut-off-your-brain, relax-your-shoulders, work-on-your-tan, tropical island vacation. They literally invented the piña colada in this city! Who knows, the culture is so old that they probably invented sand and palm trees and trade winds, too. But after a week of playing dumb, we discovered that if you relax too much and you’re not careful with your heart, you can get to know San Juan a little bit—and you might just fall in love with the place.

When my wife and I landed in Puerto Rico, we weren’t exactly sure what we were getting into, but we showed up reasonably prepared. We were familiar with the accounts of Hurricane Maria devastation, of course, and had read about the thorny politics of Puerto Rican statehood that stretch back a century. One guidebook urged a cautious postcolonial etiquette: Don’t talk to the locals about politics—yours or theirs—because they can’t vote on the mainland and you wouldn’t want to needlessly offend. So we would concentrate on eating and drinking and swimming and sunbathing. You know, the easy stuff.

Our first three days were spent at a golf resort 30 minutes outside of San Juan. At the St. Regis Bahia Beach in Rio Grande, we were pampered and primped, swanning through the lushly landscaped grounds, lazing by the private beach or in the gigantic pool, swilling perfectly creamy piña coladas without a thought beyond the genius who made the one we were sipping—let alone the genius responsible for making the first one ever.

At the end of our stay, we took a $20 Uber to Old San Juan and checked into the Hotel El Convento, a 17th-century Carmelite convent that had been renovated into a boutique hotel by the Woolworth family in the 1960s. El Convento sits right across the street from the Catedral Metropolitana Basílica de San Juan Bautista, the second-oldest church in the Western Hemisphere, first built with wood and straw in 1521 and now the marbled final resting place of the conquistador Juan Ponce de León. After a walk around the block in Old San Juan, it was painfully obvious that an island vacation here can get as deep as your heart will let it get.

That night, we ventured into another neighborhood, Santurce, to visit the acclaimed Jose Enrique, a restaurant just off La Placita, the square where the entire city—not just the tourists!—congregates to buy produce during the day and to drink and smoke and dance at night. Jose Enrique is the most famous restaurant on the island, first because its namesake chef fed his people during their time of greatest need, in the aftermath of Maria, at one point serving 20,000 meals a day. And second, because the cuisine is actually delicious—Enrique’s creativity and skill has made his restaurant the epicenter of Puerto Rico’s farm-to-table movement and the most inclusive fine-dining experience in the Caribbean. He builds his menu based on what he can get his hands on that day and puts it on a dry erase board, letting his servers guide you. I’ll make it even easier: Order everything you can. The night we were there, we ordered the minutas, a mess of tiny, deboned snapperlike fillets on a bed of yam mash, and the combination of crispy fillet and sweet mashed-up yam hit me in that ancient reptilian part of my brain that I thought only the perfect ratio of pineapple to coconut with rum could reach.

After dinner, we took another Uber to El Batey, a dive bar across the street from El Convento. You could smoke cigarettes in there, and where there is smoke, there’s a Puerto Rican journalist who wants to talk politics with his American compatriots from the mainland. We were full of tiny fish, drunk on Don Q and openly violating the guidebook’s ban on politics. After an intermittent period of laughter and Spanglish and trying to sound smart, we stumbled back to our room, glancing over the adoquines, shimmering blue in the moonlight. The mind reeled, thinking about how these cobblestones were originally ballast on a Spanish ship. Perhaps you came here for the “typical” island vacation—chances are, you’ll get more than you bargained for.


Where to Dance

Criollo culture is a cocktail of Spanish, African and American influences—you can taste it in Puerto Rico’s cuisine, but you can also hear it in its music. Located in the heart of Santurce, La Respuesta is where the locals come to shake it.  

Where to Read

Book a private tour of the collection of La Casa del Libro in Old San Juan. Located in a beautiful colonial building in the heart of the historic city, the collection includes the earliest map of the island and a royal cedula issued by King Ferdinand and Queen Isabella authorizing the facilitation of Columbus’ second expedition. 

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