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3 Perfect Puerto Rico Itineraries

There’s a reason why Puerto Rico is known as the “island of enchantment”—all types of travelers can easily fall in love with the Caribbean destination. Cosmopolitan types find the capital city of San Juan to be a treasure trove of history, culture, and style; yachters looking for some solitude can’t beat the boating scene on east coast, which is the gateway to the sister islands of Vieques and Culebra; and the surf is always up for thrill seekers and beach bums on the west coast. Follow these three perfect itineraries to enjoy Puerto Rico’s sunniest sides.

The City


Founded in 1521, the historic center of Old San Juan is the oldest city in the US. Ancient and arty at the same time, the old city is only 7 blocks square and an entire day can be spent exploring the nooks and crannies of the cobblestoned streets. Start bright and early with a café con leche at Caficultura, in a classic Spanish-style house perched right on Plaza Colon. Down the block, Cafeteria La Mallorca is a great spot for a grab-and-go breakfast—the Mallorca sandwich—puffy, buttery rolls filled with eggs, cheese, and ham and topped with powdered sugar.


Once fueled, sightsee via foot (or via a free trolley—look for the numbered stops), being sure not to miss landmarks such as La Fortaleza, the Governor’s mansion, and historic forts San Cristobal and El Morro. Enjoy El Morro’s vast lawn, especially on Sundays, when kite enthusiasts come to catch the ocean breezes. Hungry? If it’s Saturday, pop into the Mercado Agricola Natural, tucked in the courtyard of the Museo San Juan, for a vegetarian sancocho and other healthy prepared foods. Or join San Juan Food Tours for a roving feast. Walk off lunch along the stunning Paseo de la Princesa to take in breathtaking harbor views.

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At Pier 2 at the foot of the walled city, hop on a quick ferry to Cataño across the harbor to the Bacardi Rum Distillery. Taxis await on the other side to whisk visitors over for a tour and a tasting to learn about the island’s favorite spirit. After the tour, return to the walled city via ferry, and take a break. Put your weary feet up, and have them massaged while enjoying a cocktail at Anam Spa and Cocktail Lounge on Calle Cristo. For dinner, sample chef Peter Schintler’s exquisite cuisine at Marmalade, with signature dishes such as tiny white bean soup with scallions, black truffle, and pancetta dust. Cap off the night at one of the old city’s storied dive bars, such as El Batey or El Farolito (Calle Sol 207). Or salsa the night away at Nuyorican Cafe.

Where to Stay: El Convento is an elegant, converted convent right in the heart of the Old City.

The Beach


Some of the island’s most beautiful beaches are on Puerto Rico’s west coast in Rincon. A 2½ – 3 hour drive from San Juan (or a 30-minute jaunt from Rafael Hernandez Airport in Aguadilla), it’s worth the trip for the sand, surf, and slower pace. The perfect day begins with breakfast in the hills at The English Rose a charming inn with sprawling mountain and ocean views. Dishes like eggs Benedict and “The Full Monty,” a classic British assembling of bacon, sausage, two eggs any style, tomatoes, mushrooms, “bubble and squeak” have won such fierce fans that waits can stretch up to two hours without reservations. Then, hit the ocean with Taino Divers to catch a glimpse of beautiful coral reefs and sea life like lion fish, dolphins, and lobster. The coast is also rife with whales; Taino Divers offers excursions for spotting the frolicking mammals, too.

And then, there are the beaches. Maria’s Beach is the sweet spot for surfers. Need a lesson? The dudes at Rincon Surf School are your go-to guys. Steps Beach is the stop for snorkelers; while sunbathers enjoy the placid waters of Sandy Beach or Antonio’s Beach. Sun and swimming work up the appetite, so grab some of the area’s best empanadillas, fried turnovers stuffed with seafood, fish, or meat, at El Patio Familiar (Route 115 at km 12, 787-431-8482). Their conch and rabbit-stuffed varieties are among the area’s most delicious. Sunsets are best at Tamboo Bar at Beside the Pointe Inn at Sandy Beach or Calypso Cafe at Maria’s Beach. Shake off the sand and dress for dinner at the dignified Restaurant Aaron at the Horned Dorset Primavera, where the local lobster tail may be accompanied with French foie gras.

Where to Stay: Horned Dorset Primavera is a seaside estate with exemplary service and the area’s most sophisticated dining.

The Boat


The pirates of the Caribbean may be long gone, but there are plenty of sailors looking to castaway on Puerto Rico’s east coast. The port town of Fajardo has marinas full of boats in every size. Breakfast at La Vista Café (83 Calle 2 (787) 655-7053), is a great spot for rooftop harbor views and well-made classics such as French toast and pancakes. Then set sail with East Island Excursions on a catamaran, complete with glass bottom and water slide. Spend the day snorkeling in the crystal-clear waters around Icacos Island or discover the hidden coves of Culebra while enjoying lunch, soft drinks, and rum drinks on board.

Upon return in the afternoon, dry off, and have cocktails and an early dinner at the atmospheric La Estacion. Chef Kevin Roth’s traditional whole roasted pig recently won the Cattleman’s BBQ Caribbean BBQ competition for best lechon. His whole pig feast on Sundays includes an all-you-can-eat platter piled with belly, loin, ribs, shoulder, crispy skin, and sides of traditional rice with pigeon peas and escabeche of local tubers. Once darkness has fully settled in, explore the glow-in-the-dark waters of Fajardo’s own bioluminescent bay via kayak with Eco Adventures. Or catch the evening boat to Vieques for a catamaran trip, and dinner, through radiant Mosquito Bay.

Where to Stay: El Conquistador Resort offers a casino, private island, and beach, and is conveniently located for all Fajardo excursions.

Photo credits: Courtesy of Hernan F. Rodriguez

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