The Caribbean: Jamaica
For a weekend
What's the best Caribbean vacation that's close by and lets me try two different hotels? Jamaica. Stay in a mountain-view room at Strawberry Hill in the Blue Mountains above Kingston, then take a helicopter to Villa 10 (if you can get it) at Round Hill. Jackie and J.F.K. stayed here, and it still does the trick. Strawberry Hill: Rooms, $325-$775; 800-688-7678, 876-944-8400; www.islandoutpost.com. Round Hill: Rooms, $850-$3,140; 800-972-2159, 876-956-7050; www.roundhilljamaica.com.
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