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Road, Town, Tortola, British Virgin Islands

It's one thing to visit a Caribbean island for a vacation. It's another to make the pristine British Virgin Islands your destination of choice. But there's nothing quite like escaping to a private island in the British Virgin Islands—especially when it's the home of and playground for the Peter Island Resort.

The resort has piled up plenty of stellar accolades and is consistently...

Old San Juan, Puerto Rico
Even though Hotel El Convento is not on the beach, no list of San Juan's top hotels is complete without mentioning it. The hotel occupies a 350-year-old former Carmelite convent in an attractive part of Old San Juan. Its present-day splendor is all the more impressive given its history: after 250 years as a nunnery and cloister, the structure served less and less reputable functions, from retail...

Gros Inlet, St. Lucia

On the Caribbean island paradise of St. Lucia, Sandals' prime real estate dominates a slender peninsula with the sea virtually all around. Sailboat-dotted bays, volcanic mountains, and tropical greenery will take your breath away... and that's before you've even stepped into the grandiose colonial throwback that is the Sandals Grand St. Lucian.

Beneath its rather nondescript...