An Insider’s Guide to the Caribbean

It isn’t too early to start planning for your sun-drenched winter vacation in the Caribbean. But which island will offer you the best experience? It all depends on your particular travel dreams. Here’s a thumbnail guide to help you decide.

The Best Island . . .

For Celebrity Spotting: St. Barthélemy
Chic, oh-so-French St. Barths (pronounced “Barts”) not only boasts celebrities by the score, it is also one of the most gay-friendly Caribbean islands. St. Barths is far from a bargain destination, but it delivers value in every way — from perfect French food to intimate five-star hotels to 17 glorious beaches and great shopping (skimpy French bikinis are big bargains now, thanks to the weak euro). Choose between renting a villa in the mountains (many have magazine-cover views) or booking into one of the small luxurious hotels on the beach. You will also need to rent a car to get to the best island beaches. The price is high, but if your dream vacation is to share a strand of sand with the likes of Beyoncé, Lindsay Lohan, Derek Jeter, Mariah Carey, Michael J. Fox or Sean Combs, it’s worth the splurge.

Language: French; Location: The Leeward Islands; change to a small plane in nearby St. Maarten/St. Martin for a 10-minute flight with a somewhat dramatic landing; or take the ferry over.

For Honeymooners: St. Lucia
Think of St. Lucia, and the Petite and Gros Pitons — those two steep, lush green mountains overlooking an impossibly blue sea — immediately come to mind. That romantic setting draws honeymooners from all over the world. Many of them book into Ladera, arguably the island’s prettiest resort, which offers close-up views of the pitons from your suite or villa. You will also have a private plunge pool (and maybe a waterfall), and your suite will have no fourth wall. That lets you enjoy the cooling breeze and see the sun set sans glass (no one can see in). If you want a livelier, right-on-the-beach scene, the Sandals Grande St. Lucian Spa & Beach Resort in the north — tucked between the Atlantic and Rodney Bay — wins raves. It has beachfront rooms, four huge pools, sports galore, a lively nightclub and lots and lots of young fellow honeymooners (plus shuttles run to the two other St. Lucia Sandals, which offer exchange privileges). Of course, there is a lot to do away from the resorts, but many couples simply stay right where they are.

Languages: English, French Creole; Location: Lesser Antilles, Eastern Caribbean; some nonstop flights available, some require a change in San Juan.

For Nature Lovers: Tobago
Bird watchers (and bargain hunters) flock to the tranquil, easy-going island of Tobago — next-door neighbor to bustling Trinidad — in the southern Caribbean. Tobago doesn’t have a vast tourist infrastructure, which keeps the numbers low and the pace slow. That said, its coastline is dotted with some of the prettiest, most secluded beaches in the southern Caribbean. Its biggest draw, however, is its large protected rainforest, the oldest, and arguably most pristine, in the western hemisphere. Hire a guide to point out more species of birds than you’ll ever see in one day again. The island’s marine parks also abound with tropical fish in designer colors. The price is right, too, on Tobago. You can still get all-inclusives for two for under $200 a night. Bigger, more expensive hotels are arriving however, so go now to experience the gentle, old-fashioned Caribbean.

Language: English; Location: Republic of Trinidad and Tobago; Windward Islands (not far from the coast of Venezuela); you may be able to get a nonstop flight to Trinidad, then take a puddle-jumper to Tobago; some flights go directly to Tobago via San Juan.

For Chilling Out: Virgin Gorda
Sometimes you just want to get away from it all, really away from it all. That’s when you go to Virgin Gorda. It’s not glitzy. It’s not about nightlife or seeing and being seen. It is about sheer, utter relaxation. Fly into Tortola’s Terrance B. Lettsome International Airport then arrive at Biras Creek Resort, on Virgin Gorda’s North Sound, by boat. Check into one of the 31 suites that dot 140 acres of postcard-perfect grounds. Ride your bikes down to the beach for lunch. Know that dinner at this Relais & Châteaux property will be superb. The wine list is endless, and the sommelier makes choosing seem like a delightful game. Spend a day touring Virgin Gorda, one of the most beautiful of the 50-plus British Virgin Islands. Make sure you stop at the Baths, a maze of natural grottos and boulders shaped by the sea. Pick up t-shirts in Spanish Town for the folks back home, and keep an eye out for Morgan Freeman, who docks his boat there.

Language: English; Location: British Virgin Islands, just east of Puerto Rico; change in San Juan for the short flight to Tortola; go to Virgin Gorda by boat.

For Partying: Aruba
Okay. You are young and energetic and your idea of a vacation to is to play the night away. Book your flight to Aruba now. This small island Dutch island, roughly 20 by six miles, is party central, and the real nightlife doesn’t even start until about midnight. If you want to get ahead of the game, however, you can board the Kukoo Kunuku, the psychedelic red party bus (a ’57 Chevy) at your hotel as early as 6 p.m. It will take you and all your new friends to the beach for a glass of champagne, to dinner at an Aruban home or restaurant, and then on to three bars. Think of it as a designated driver on a grand scale. If you choose to go on your own, there is good karaoke at Choose-a-Name and equally good trance at the neighboring Tantra-both in the Royal Plaza Mall in Oranjestad. Aruba’s casino action goes late, too, with the Crystal Casino at the Renaissance Aruba getting high marks. By day, this near-desert-island is well worth exploring, and there is a good Numismatic Museum. Or, you might just choose to snooze on the beach. That works, too.

Language: Officially Dutch, but English is universally spoken; Location: In the southern Caribbean, close to the Dutch islands of Curaçao and Bonaire, and near the coast of Venezuela; Nonstop flights from many major American cities.

For Shopping: St. Thomas
St. Thomas, in the U.S. Virgin Islands, is still Caribbean bargain central for U.S. residents. The reason: Those returning to the States enjoy a $1,600 duty-free exemption. Look for deals on everything from fine jewelry (good prices on diamonds and emeralds) to linens, china and crystal, which they will ship for you. There are also great prices on liquor, perfume and high-end designer sunglasses. The genuine local products — the hand-carved calabash bowls and home-crafted dolls — are charming. You may have better luck haggling in the smaller mom-and-pop shops than in the big stores designed to process legions of cruise ship shoppers quickly. Of course, no one is likely to take a vacation just to shop. St. Thomas is rich in high-quality resorts, from the Ritz-Carlton to the Wyndham Sugar Bay Resort & Spa, but there are good accommodations in every price range. Save some time to tour historic Fort Christian, which dates back to 1680, and the Seven Arches Museum, a handsomely restored 18th-century home. Then go fishing.

Language: English; Location: Leeward Islands, just east of Puerto Rico; Nonstop flights available from some cities; many flights require a change in Puerto Rico.

For Diving and Snorkeling: Roatán
The good news is that you are probably saying, “Roa . . .where?” This little slip of an island in the Western Caribbean, 40 miles long and just two miles wide at its widest point, has long been off the radar screen for everyone except really dedicated deep sea divers. Now, the word is out. Roatán, one of Honduras’ Bay Islands, near the second largest barrier reef in the world, is simply perfection for people who like to see under the sea. Think 500 different types of fish swimming in water so clear you can spot them from the plane as you land. Roatán is also one of the least expensive places to learn to dive. Anthony’s Key Resort, a PADI Gold Palm 5-Star Instructor Development Center, has done just that for more than 40 years. One you’ve mastered the skill, there are great wreck dives, including El Aguila, a 230-foot cargo ship now inhabited by garden eels. Snorkeling along this vast coral reef is another great pleasure. Accommodations are reasonably priced on Roatán. The new Turquoise Bay Resort is a bit more posh than most, has a great restaurant and also has a fully-equipped Dive Center.

Language: Spanish, but English is fairly well known; Location: Western Caribbean, off the coast of Honduras; it is possible to fly nonstop to Roatán from Newark, Houston, Atlanta and Miami.

For Families: Jamaica
Jamaica is a great family destination, simply because there is such good infrastructure for kids in the hotels and so much to do when the family is out and about. Some resorts, including the ultra-posh Round Hill (Ralph Lauren is one of the owners), the all-inclusive Runaway Bay, and Sunset at the Palms on Negril Beach, offer extensive children’s programs. Half Moon, near Montego Bay, has its own private children’s village, complete with nannies. Kids’ programs typically include everything from nature walks to dress-up parties to reggae classes. Off property, older children love to climb the slippery steps up Dunn’s River Falls, to float down the Martha Brae River on a raft made from bamboo or to get their hair braided on the beach. Sampling spicy jerk chicken or pork is a “hot” treat they won’t soon forget. Horseback riding along water’s edge will delight older kids. Simply meeting the warm and friendly Jamaican people — including those their own age — will probably be the activity they enjoy most of all.

Language: English; Location: Greater Antilles, due south of Cuba; great range of nonstop flights from American cities via Air Jamaica and others.