Jamaica: Round Hill Resort 

Round Hill has hosted its share of icons--from Elizabeth Taylor to Fred Astaire--but every guest is treated famously. A driver picks you up from Montego Bay Airport for the 30-minute ride to the resort, where louvered doors open to private balconies overlooking tropical plans and the beach from each of the stone-floored, Ralph Lauren-decorated oceanfront rooms.

Go Ahead, Indulge: Sit at the thatched-roof beach bar and sip an ice-cold Red Stripe while checking out the surf.

Make A Date: Call for a dinner reservation at the nearby Tryall Club and request the private water-front gazebo. Enjoy local seafood as waves lap in the background; 876/956-5660.

Best Sunset: Float to the edge of the infinity pool for unobstructed views of the pink, purple, and gold sky.

Rates: From $579; 876/956-7050 or roundhill.com