Upon arrival in San Juan, kick-start your vacation with dinner among locals at the eponymous restaurant of 2015 James Beard finalist José Enrique. His no-frills dining room is eternally packed, and the queue inevitably spills into the street. Come early and make friends with the neighborhood regulars while you wait for coconut water cocktails and swordfish fritters in house hot sauce. When it’s time for a digestivo (the mood here inspires anything but sleep), follow an off-duty chef to La Factoria, an unmarked mixologist’s lair that occupies a historic corner building in the heart of Old San Juan. Inside, friendly bartenders flavor tropical concoctions with fresh passion fruit and homemade ginger syrup. Spend the night at St. Regis Bahia Beach, a luxurious stay for families, golfers, nature lovers and spa junkies—and anyone keen on waking up within steps of a splendid stretch of sand.
Sun worshippers of all stripes will want to take in the lush landscapes (and plenty of fresh Caribbean air) beyond the San Juan city limits. Outdoors enthusiasts can spend the day among wild orchids, waterfalls and chirruping coquí frogs in El Yunque National Forest, the only tropical rainforest on U.S. soil. Happily, for travelers with children, El Yunque’s canopied picnic areas and hiking trails are a mere half-hour drive from the capital. The lush forest is also a haven for adrenaline-pumping activities, including horseback riding, ATV tours, zip-line courses and more. Meanwhile, epicures favoring a more leisurely outing can entertain themselves as the locals do with a few hours of seaside grazing and revelry in neighboring Piñones. This laid-back beach community springs to life on Saturday afternoons when locals flock to its boardwalks for their weekly fix of street music and frituras (fried local delicacies sold at rustic kiosks).
Greet the day with San Juan’s coffee cognoscenti at the family-owned Café Hacienda San Pedro. A bag of single-origin beans—hand-harvested a few hours away by fourth-generation growers—makes a lovely and aromatic souvenir. Properly caffeinated, make your way to the islet of Old San Juan to tour the Spanish-colonial city’s blue cobblestone streets and its iconic 16th-century fortress, Castillo San Felipe del Morro (“El Morro”). Thanks to sweeping ocean views and a constant breeze, the citadel’s esplanade is popular not only with history buffs, but also with kite aficionados. Many neighborhood shopkeepers stock reasonably priced kites should you wish to join them. Otherwise, it’s on to La Casita Blanca, a venerable luncheonette fit for an old-fashioned farewell feast. Bid the island adios with fresh guava juice, seafood arepas and a whiteboard menu of meaty staples that would make any homesick Puerto Rican swoon.
Or, better yet, hop a 25-minute flight and spend a few nights on one of Puerto Rico’s offshore isles—perhaps at the W Retreat & Spa Vieques Island? You’ve covered a lot of ground in 36 hours, but just wait until you see Culebra Island’s fabled Flamenco Beach.