St. John
Thanks to Laurance Rockefeller, whose land donation in the 1950's turned two-thirds of the
island into a national park, St. John is, and will remain, among the most pristine and low-key
spots in the Caribbean. You won't find many beachfront villas; most houses are in the hills
above the west and south coasts, or near Coral Bay, the sleepy east side settlement at the
end of a long, sinuous mountain road. (Though Coral Bay is lovely, it is not the place to
rent if you plan to make frequent trips to town.) Don't come expecting much entertainment
beyond what you'll see through a snorkeling mask.
Jamaica
Nonstop flights from many major cities make this sprawling, mountainous island (the Caribbean's
third largest) particularly attractive to families with young kids; also appealing is the
fact that most rentals come with a full staff, including energetic nannies. Look for great
family properties along the beachy north coast near Montego Bay; many have grassy lawns and
game rooms, as well as access to facilities and kids' programs at nearby top-notch resorts
such as Round Hill and Tryall Club. Golf, river rafting, waterfalls, horseback riding, and
shopping are easy day trips away—if you can talk anyone into getting out of the pool.
Barbados
A well-developed, easy-to-get-to, and unintimidating destination—ideal for first-time
Caribbean-goers and Anglophiles. Villa options range from opulent, staffed estates on the
quietly glam west coast to simpler digs on the more rollicking, pub-lined south shore. Families
will be kept busy snorkeling, windsurfing, and Boogie boarding (waves are biggest on the Atlantic
coast). The underground tram ride through Harrison's Caves is a big draw, though claustrophobes
may want to skip it and go directly to afternoon tea, which is served at many hotels, including
the posh but surprisingly kid-oriented Sandy Lane.
Virgin Gorda, British Virgin Islands
Long a favorite stopover with the yacht-chartering set, the hilly, arid, lightly developed
Fat Virgin is increasingly being discovered by landlubbing vacationers. Casual, open-to-the-trade-winds
villas offer access to sublime boating, fishing, and hiking (especially in Gorda Peak National
Park), plus extraordinary beaches. Don't miss the Baths, where a jumble of giant boulders
form grottoes and secret pools (go early before day-tripping cruise ship passengers arrive),
and the Crawl, a rock-rimmed lagoon perfect for young snorkelers.
Anguilla
If your family is content killing the day on a perfect sweep of white sand, consider this
tiny, fashionable yet unpretentious coral outpost, 20 minutes by ferry from bustling St. Martin.
Many impressive spreads (including Villas of the World's No. 9033, shown below, rented by
Brad Pitt and Jennifer Aniston, pre-split, for $10,000 a day) are right on the electric-blue
water. Though dining is serious business here—a case in point is the Malliouhana restaurant,
with its ambitious French menu and 25,000-bottle wine cellar—you may be just as happy
getting sticky fingers at Uncle Ernie's or one of the many other terrific beachfront BBQ shacks.
Necker Island, British Virgin Islands
Family reunions don't get any more luxe, or more secluded, than on this 74-acre palmy hideaway.
Your party of up to 26 can have the run of the place—when owner Richard Branson, the
Virgin Atlantic tycoon, isn't in residence. Forty-two-thousand dollars a day gets you the
handsome stone nine-bedroom hilltop Main House and four one-bedroom thatched-roof Balinese
villas. You'll also get the use of a water-sports center, stocked with the latest kite boards,
Windsurfers, and sea kayaks; a fleet of power- and sailboats (with skippers); four pools;
a cliffside open-air spa (treatments cost extra—if you can believe it); all meals and
drinks; and a highly attentive (and ridiculously good-looking) young staff of 42. Oprah Winfrey,
Steven Spielberg, and Princess Diana have all stayed here—look for the schoolboy scrawls
of Princes William and Harry in one of the guest books.
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