San Juan Puerto Rico
Credit: Brian Pineda

Puerto Rico is easily the Caribbean’s most convenient destination (JetBlue offers multiple flights a day from New York City). San Juan’s Old Town is always good for a stroll, but there’s more elsewhere, like these six highlights.

Aaron Stewart Home

A pair of ex–New Yorkers have created the ultimate spot for souvenirs everyone will love, particularly the brightly printed pillows, textiles, and ceramics.


A tiny hole-in-the-wall next to a gas station serves native versions of pubby offerings, like steak-and-rice egg rolls and porchetta, ricotta, and tomato on brioche toast. 562 Calle Cuevillas; small plates $7–$17.

Condado Vanderbilt

At this 319-room hotel in a Spanish Revival–style building, there's a lovely beach and a great restaurant, 1919; the tuna tartare will blow your mind.; doubles from $365, entrées $36–$48.

Olive Boutique Hotel

The foil to mega-hotels in Condado, this 15-room stay has a Soho House–style rooftop club. At Sage, order the yuca gnocchi.; doubles from $169, entrées $29–$45.

Bar Gitano

Spanish-style tapas and paellas, along with potent sangria, are always flowing from the kitchen and bar. Live flamenco plays two nights a week. 1302 Avda. Ashford; tapas $6–$14.

Jose Enrique

The very popular restaurant from a James Beard Award winner turns out dishes like fish fritters and grilled mahimahi and has a cult following.; entrées $14–$58.