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. aaronstewarthome.com.
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.
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. condadovanderbilt.com; 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. oliveboutiquehotel.com; doubles from $169, entrées $29–$45.
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.
The very popular restaurant from a James Beard Award winner turns out dishes like fish fritters and grilled mahimahi and has a cult following. joseenriquepr.com; entrées $14–$58.