Itty Bitty Puerto Rico

The Best Little Adventures on the Island

Adventure One: Street Food
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San Juan

The best of all worlds, a stroll through vibrant Old San Juan by night showcases some of the New World’s most beautiful Spanish colonial architecture, mighty and mysterious fortresses, and sultry night life. But for the purposes of this Itty Bitty Journey, the highlight of Old San Juan is the line-up of food trucks on the Plazoleta del Puerto, where the Pinchos are flavorful and cheap, and seasoned ground meats and fishes are expertly stuffed into various pastries and deep-fried in all sorts of exquisite fashions. Tropical drinks novel and familiar grace the menus at virtually all of the kiosks, and somehow the sweetness seems to cut the grease appropriately. When you’ve had your fill, saunter down the Calle Recinto Sur to Inaru. Skip the outdoor dining and head straight to the bar, where the remarkably warm and intuitive bar staff act as matchmakers between people and drinks. Don’t bother to look at the menu. Just ask them what they think you should have.


The whole island is a treasure trove of street meats, some questionable and some legit, but for a breathtakingly well-established roadside snack scene, visit the Lunquillo Kioskos. Ranging from fancy-pants to frightening, with everything in between, over 60 kiosks sit side-by-side and showcase Puerto Rico’s wealth of informal culinary brilliance. You want pastellitos. And a cold Medalla.

Adventure Two: Best Beaches

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If you’re venturing out to the Rio Camuy Caves or to the impressive observatory at Arecibo, leave time in your day for a stop at the Guajataca Tunnel. Nestled at the eastern edge of a chain of Puerto Rico’s most picturesque beaches, a historic train tunnel hosts a walking path that connects a curious assortment of ruins. Saunter around the remnants of a long-forgotten train platform or hike over a giant and apparently purposeless wall, all the while breathing in the tropical flora. When the spirit moves you, bury your toes in the perfect, silky sand and stare for a bit at the considerable surf. Bonus Points: On the return through the town of Arecibo, stop at El Farol for what we believe is the best Churrasco on the island. This little haunt is humble, to be sure, but by the end of the meal you’ll be well-fed, and friends for life with the proprietor and his family.

Mar Chiquita

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We asked our favorite bartender in San Juan where the prettiest beaches were, he told us to explore Manatí. Hidden away from well-traveled roads, the beaches of the region are largely empty save for summer weekends, when Puerto Ricans escape the heat of the city for adventures by the sea. Perhaps the most unique among Manatí’s beaches is Mar Chiquita, where a narrow inlet through natural limestone walls creates a crescent-moon shaped cove. Here, waves build on themselves as they’re channeled into the lagoon, generating a hypnotic display of hydrodynamics at work. Around the beach, wild dogs wait for vibrantly painted kiosks to open, hoping for a morsel from a generous stranger. Old walls and abandoned structures gather ornate graffiti, providing shutterbugs with ample opportunity to fashion vacation-art. In the cove, the water ranges from still to wildly inhospitable, and it should be noted that undercurrents can be strong during ebb tides, particularly in the winter months.

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Adventure Three: Ittier, Bittier Islands

Travel guides of various sorts debate the merits of Puerto Rico’s satellite islands of Culebra and Vieques, and each island is in itself worthy of a relaxed beach vacation. But travelers wishing to balance a remote island experience with access to Puerto Rico’s diversity might want to consider the luxe villas at the Waldorf Astoria’s Las Casitas Village in the port town of Fajardo. Though the rack rate on rooms can be breathtakingly high, persevere: reasonable rates appear often on discount travel sites, and the resort itself often runs last-minute specials. With boat access to the resort’s private Palomino Island, one can swim and explore the shoreline of the 100-acre treasure by day, and enjoy Fajardo’s charming restaurants by night. A tiny rental shack provides access to a host of water toys, ranging from Sea-Doos to Hobie Cats. Hire a kayak and venture a few hundred yards to Palomonitos Island, the tiny cay that made a cameo in Pirates of the Caribbean: On Stranger Tides. A single palm tree adorns this minute isle, which is rumored to be rapidly disappearing into the sea. Feeling like a landlubber? Venture out on a trail ride with the island’s own stable, where ranch hands are happy to help you pick up chicks when your ride is over.

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The Rundown: There’s a reason that Puerto Rico was named one of Travel and Leisure’s Hottest Travel Destinations for 2013. Just go.

Where to Stay: San Juan: The San Juan Water Beach Club. Affordable and chic. Great rooftop bar. Minimal touristy corniness. Fajardo: Las Casitas Village. Lovely villas. Beautiful pools. Private island access. Pricey, but you can find good deals, and you don’t need to pay for adventures once you’re there. 

What to Eat: Street Food. Churrasco. Mofongo. Piragüas. Pastellitos. Pinchos.


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