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-PR-Gear-Patrol 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-PR-Gear-Patrol 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.
What-To-Do-PR-Gear-Patrol What to Do
By all means, do eat, drink and window-shop your way through Old San Juan’s centuries-old historic architecture. But try to avoid the midday hours, when behemoth cruise ships unleash armies of dawdling, sun-crisped tourists on the blue-cobbled streets. There’s a whole urban landscape to explore outside of the old town, and a good place to start is Mercado Santurce, an ancient market where you can forage for fresh produce before hitting up one of the city’s impressive art museums. On the way, get a pick-me-up from Hacienda San Pedro Coffee Shop, the urban outpost of one of the island’s oldest, most prestigious coffee plantations. Afterwards, take shade under a beachfront palm at Ocean Park, or hit the surf at La Ocho, a big, steady break that rips right inside city limits near Escambrón Beach (nearby, La 8 rents boards by the hour). Come nightfall, you can soak up the swanky atmosphere at La Concha‘s lobby bar, where the city’s beautiful people sip cocktails and gawk at each other under pulsing, rainbow-colored ceiling lights.
Venture-Out-PR-Gear-Patrol Venture Out
Puerto Rico offers more territory to explore than many tropical islands (Aruba, the Bahamas and Turks and Caicos all spring to mind), but its relatively efficient American infrastructure means that no corner of the island is more than 2.5 hours from San Juan. An hour southeast of the city, drive up into the Sierra de Luquillo to explore the jungle pathways of El Yunque, where rain-swollen rivers cascade through the only tropical rainforest in the national forest system. Make sure you arrive early, before massive tour buses unleash a stampede on the intimate trails. Northeast of El Yunque, coral reefs protect the golden sands of Luquillo Beach from the pounding North Shore surf. Of course, nowhere is more laidback than Culebra, a tiny spit of pristine beaches that’s offshore of Vieques, which is off the eastern shore of Puerto Rico. To max your time relaxin’, hop a 30-minute Cape Air flight from the San Juan Airport.

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