The study at Roundhill Jamaica.

ROUND HILL | MONTEGO BAY, JAMAICA

The Scoop: If it’s good enough for John F. Kennedy and wife Jackie to visit multiple times (he even wrote his inauguration speech in his cottage here), you can bet the privacy and luxury at this resort are at the top of their game. One of the most beautiful and elegant boutique hotels in the Caribbean, this celeb hotspot is a truly  lush escape. It has remained among the most elite resorts since its opening in 1953.

The Difference Maker: The oceanfront guest rooms of the Pineapple House were designed by fashion icon Ralph Lauren, who gave them an easygoing Nantucket vibe. Sink into four-poster king beds and soak in deep tubs, two amenities that never, ever hurt in a hotel room.

Day Tripper: When in the Caribbean it would be almost sacrilege to not test out the waters, including the rivers in Jamaica. Enter bamboo river rafting. Climb aboard a 30-foot bamboo raft and skillfully pole (or have your local captain do the work) the raft through the jade-green waters of the Martha Brae River located in the parish of Trelawny (a.k.a. birthplace of Olympic record-breaker Usain Bolt).

Visit roundhill.com to learn more.