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Top 10 historic hotels in the Caribbean

Top 10 historic hotels in the Caribbean

Posted by Shanelle Weir on May 28, 2014

Caribbean hotels and resorts are among the finest in the world, with the best of them offering vibrant interior design and cutting-edge technology. But a handful of hotels have something that's impossible to create from scratch: an authentic historical heritage. The oldest of these properties dates back to the 16th century; others are former 18th-century plantation houses, while some are iconic properties from the 1950s. Below are 10 of the Caribbean's most appealing historic hotels.

Hostal Nicolas de Ovando, Dominican Republic

Santo Domingo's Colonial Zone is packed with historical treasures, including the 16th-century Hostal Nicolas de Ovando, named for the property's original resident, Governor Nicolas de Ovando, the first governor of the Americas. The Dominican Republic hotel comprises three houses with thick stone walls, hacienda shutters and sun-splashed courtyards. Choose one of the Colonial rooms for the ultimate back-in-time experience. Given the hotel's history, it's a surprise at how hip the ambience is, with Santo Domingo twenty-somethings enjoying an evening cocktail by the pool while a D.J. lays down tropical beats. The hotel's Cibao Bar presents a selection of rums from 12 different Caribbean countries as well as a choice of primo Dominican cigars.

Graycliff, The Bahamas

This hotel has a storied past. The structure dates back to 1666, when it was the first Anglican Church in Nassau, The Bahamas. The church was destroyed by the Spaniards in 1703 and then rebuilt as a garrison in the 18th century. Graycliff mansion was constructed in 1740 by the notorious Caribbean pirate, Captain John Howard Graysmith, who plundered the seas upon his ship, the Graywolf. The building's transformation into a place of lodging came in 1844, when it became Nassau's first inn; one of the property's most famous guests was Winston Churchill. The 20-room hotel sports a proper English atmosphere and has antique-filled rooms, a swimming pool, the Humidor Churrascaria restaurant and is the site of the award-winning Graycliff Cigar Company.

Hotel El Convento, Puerto Rico

Old San Juan is a colorful neighborhood rich in history. Originally a 17th-century Carmelite convent that was converted into a hotel in 1959, this 58-room property exudes Old World Spanish charm, with decorative glazed tiles and details, wooden beams and antique furniture. The AAA Four Diamond property has three restaurants and a plunge pool offering views over San Juan Bay. Perhaps best of all, guests are right in the heart of Old San Juan, where a sense of history is evident with every step taken along the winding, cobblestone streets.

Half Moon, A RockResort, Jamaica

A group of heavy hitters from American families with names like Firestone, Armour and Reynolds joined forces with similarly powerful Brits, Canadians and Bermudians to create their own cottage colony in Montego Bay in the mid-1950s. What they all had in common was an intense love affair with Jamaica. Half Moon takes its name from its crescent-shaped beach. In no time at all, the property became a magnet for wealthy travelers, including Hollywood stars like Clark Gable and Joan Crawford; and world leaders such as Her Majesty Queen Elizabeth II and JFK and Jackie. The sprawling 400-acre resort has a world-class spa, championship golf course, 197 guest rooms and suites, and 33 private villas.

Hotel Nacional de Cuba, Cuba

This was the number one choice of visitors during Cuba's heyday in the 1950s, before the Cuban revolution. Former guests include cultural icons like Ernest Hemingway, Frank Sinatra and Pablo Casals. The 457-room hotel was also a regular meeting place for the mob, with crooks like Meyer Lansky and Santos Traficante settling in to plot their next move. Even more famously, the hotel was the site of Fidel Castro's 26th July Movement and an integral part of the Cuban revolution. The hotel was officially opened in 1930 and sports a hodgepodge of architectural styles, from Moorish to neo-classical.

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