How to Choose the Right Caribbean Island for Your Vacation

Bottlenose dolphins jumping over water next to boat,Freeport,Bahamas
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What's the Caribbean vacation of your dreams? With more than 7,000 islands to choose from, it's not always an easy decision. The good news is that -- short of skiing or ice skating -- the islands of the Caribbean offer something for everyone.

Couples Getaways

Bermuda is great for its wonderful restaurants and pubs, sophisticated resorts, and convenience. Jamaica is the place to go if you're looking for an all-inclusive, couples-only resort. Also, St. Lucia's dramatic cliffside resorts, unique dining options, and dramatic geography make it an idyllic couples' paradise, reminiscent of the South Pacific.

Family Fun

It's hard to beat the Bahamas for a family Caribbean vacation: the Atlantis on Paradise Island and Our Lucaya on Grand Bahama Island are two of the most complete resorts in the region. Aruba also is an excellent family destination, with its friendly population and many options for off-resort activities. Families looking to go off the beaten path should consider St. Kitts and Nevis, which has old forts, haunted plantations, and a vintage railroad to explore.

Flying Solo

Safety and a great transportation system make Bermuda an excellent choice for solo travelers, although young singles may find the nightlife somewhat lacking. Curacao and Grand Cayman are other destinations with a reputation for safety that appeal to solo travelers, especially women.

Gay-Friendly Destinations

The Caribbean hasn't always rolled out the welcome wagon for gay and lesbian travelers -- in fact, some have openly discouraged gays and lesbians from visiting. But that may be changing. The Dutch and French islands of the Caribbean have developed a reputation for tolerance. Gay and lesbian travelers also tend to gravitate to islands where discrimination is barred by law, particularly Puerto Rico. San Juan has the region's best gay nightlife.

Hitting the Beach

Families love Palm Beach in Aruba for its gentle surf and wide array of watersports. Barbados is famed for the exquisite stretches of sand along its Gold Coast, home to fabulous luxury resorts like Sandy Lane. If you're looking for solitude, check out the Grenadines, where you can still find a secluded beach to call your own for a day.

Water Sports

The Caribbean may be best known for its diving: top destinations include Bonaire, Virgin Gorda, Grand Cayman, Turks and Caicos, and St. Croix; snorkelers prefer Antigua, St. Croix, and St. John. The trade winds that caress Aruba and Curacao make these islands ideal destinations for windsurfers; sailors tend to set course for the Grenadines or the British Virgin Islands.

More Info on the Caribbean's Best Dive Destinations

More Info on the Top Sailing Destinations in the Caribbean

Partying Till Dawn

San Juan, Puerto Rico, is the virtual capital of the Caribbean, the region's only true "city," and home to the most diverse nightlife, from all-night, Latin-flavored dance halls to fine restaurants, casinos, bars, and cockfights. For resorts that don't go to sleep at 10 p.m., head to the Dominican Republic or Jamaica. For bar-hopping and booze cruises, check out the British pubs, restaurants, and discos of Bridgetown, Barbados.

Casinos and Gaming

The best-known casino in the Caribbean -- and the most "Vegas-like" -- is the Atlantis on Paradise Island, which is also the largest hotel in the Caribbean. Puerto Rico has long been a gambler's mecca; the Wyndham El San Juan is perhaps the best-known casino, the Wyndham Rio Mar one of the newest and nicest. The Dominican Republic has the most casinos in the Caribbean, but I prefer the laid-back atmosphere of Aruba, which has a nice concentration of upscale hotel/casinos on Palm Beach.

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