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Of all the sunscreen-smeared, piña colada-drowned Caribbean vacation destinations, Puerto Rico is easily the most underrated. The US took this island paradise from Spain more than a century ago, and ever since, it’s barely registered in the American imagination. There’s no popular literature describing its pristine beaches and steamy rain forests (unless you count Hunter S. Thompson’s Rum Diary, which describes San Juan as “cheap, sullen and garish”) or music celebrating the deep-rooted culture. Hell, even the Beach Boys snubbed it in their No.1 hit “Kokomo” in favor of crime-ridden Port-au-Prince and volcano-ravaged Montserrat. It’s as if, by virtue of being an American territory, Puerto Rico is somehow too familiar.
But there’s plenty new to love on this Connecticut-sized island, especially if you steer clear of sterile all-inclusive resorts and stay in the vibrant, history-rich capital of San Juan. Set on the north-facing Atlantic coast, near the foot of the Sierra de Luquillo mountains, the 500-year-old city is both the gateway to the interior — within easy striking distance of deserted beaches, perfect swells and jungle-draped mountains — and itself a destination worthy of exploration. Hop an easy four-hour (passport-free) flight from NYC, and you’ll discover a blend of island hedonism, Old World history and American convenience that’s as intoxicating as it is exotic.
Where to Stay
If you want to stay amid Old San Juan’s narrow cobblestoned lanes and postcard-perfect colonial architecture, check in to the Gallery Inn, the lush, offbeat retreat built by New York-born artist Jan D’Esopo. Inside, a labyrinth of staircases, passageways, patios and lush gardens connect six historic townhouses. Artists-in-residence, intimate concerts and happy hours at the proprietor’s nearby beach house only make for a more singular stay. For a more laid-back location, try Dreamcatcher Guest House in leafy Ocean Park, just a block from the ocean along a relatively undeveloped stretch of beach. Stylish, handpicked vintage décor extends from the rooms to open-air kitchens, intimate courtyards and other common spaces. Start each day off right with Chef Jerome’s famous three-course vegetarian breakfast.=
Where to Eat
First off, try to score a patio seat at Caficultura, where you can sip coffee and watch the morning unfold around Plaza Colón while you wait on breakfast. Come lunchtime, Ocean Park’s trendy Acapulco Taqueria Mexicana uses fresh ingredients and perfectly spiced Mexican meats, including beef tongue and barbacoa, to elevate simple street food into high art. For happy hour, head upstairs at the European-style St. Germain Bistro & Café, where bartenders serve one of the city’s best mojitos. Be sure to request smoky-sweet Barrilito, a tradition-rich rum that’s barreled and aged locally using a century-old family recipe. For more informal local flavor, Fatty’s cooks to-die-for Caribbean fusion like jerk chicken, pigeon peas and fried plantains out of a hole-in-the-wall storefront with plastic furniture and a home-style feel.
