Which Caribbean Island Is Right for You?

Don’t know your Saint Martin from your Sint Maarten? Your Virgin Islands (UK) from your Virgin Islands (US)? For such a compact region, the islands of the Caribbean are surprisingly diverse. Below, a super-tight edit to help you — aspiring archipelago-er — decide which is the Caribbean paradise for you.

For the Future Head of State
Jamaica Inn
Ocho Rios, Jamaica

Winston Churchill slept here (in the airy, exquisite White Suite). As did Noel Coward, Kate Moss, Katharine Hepburn and Marilyn Monroe. Play a round of croquet, take a seat at Coward’s piano, kayak along the beach (possibly the adjoining topless beach). Kids might be bored but 21-and-overs will be in heaven.

For the Rock Star on a Break
Paradise Beach Resort
Nevis

Traveling with an entourage? Then you want the just-refurbished four-bedroom Ocean Villa at Paradise Beach Resort — like the Four Seasons down the road, just way, way, way more exclusive. It’s all-private-everything: plunge pool, regular pool, dinner (courtesy of an on-call chef), spa treatment — everything. Plus the close attention of a concierge (because you need to arrange a helicopter tour of the island, stat) and butler (because those bags aren’t going to unpack themselves).

For Families with Kids Enrolled in un Lycée Français
Riu Palace St. Martin
Anse Marcel, St. Martin

St. Martin and Sint Maarten share an island and an eponymous saint, but you’ll know it when you cross the border from the family-friendly Dutch Antilles to the upscale French side, where you pay for your Champagne in Euros. The all-inclusive Riu Palace is the just-right balance between the two: take the kids snorkeling on the white-sand Anse Marcel, then leave them with a grandparent and take the wife on a private sailing trip.

For the Yacht-less Tech Mogul
Eden Rock
St. Jean, St. Barts

St. Barts is as much a pitstop on the worldwide celeb circuit as Gstaad, Cannes or Sundance; it’s the island Vanity Fair called the “chic-est” in the Caribbean. There’s no shortage of over-the-top hotels for those arriving by plane rather than super-yacht (like St. Barts fans Paul Allen and Roman Abramovitch), and our pick among them is Eden Rock, which opens up to our favorite beach on the eight-square-mile island. Stay in one of two villas; our choice is the two-bedroom Villa Nina, where you can look out on the bay from the comfort of two private pools.

For the JetBlue Fan Looking to Celebrate
Curtain Bluff
Carlisle Bay, Antigua

Put it on your calendar: JetBlue starts flying direct to Antigua from J.F.K. on November 7. A sleepier — though no less luxurious — Caribbean experience than you’ll find elsewhere, Antigua offers picture-perfect, low-key beaches. Curtain Bluff, its best resort, has everything: diving, snorkeling, sailing, local cooking classes, tennis, golf…it’s the ne plus ultra of Caribbean resorts. Bring the kids.