Breakfast
Babbo chef Mario Batali takes his family to the Virgin Islands twice a year, and he raves about the breakfast buffet at the Caneel Bay resort on St. John (340-776-6111). "I've got two kids, and dining out is never easy. But they've got pancakes and omelets made-to-order, and everything else — fruit, cheese — spread out to choose from. It's only fifteen feet from the beach, so my wife and I can read the one-page New York Times fax while the boys run back and forth, grabbing a mango square or a couple of Frosted Mini-Wheats on their way. It's perfect."

Music
When Wyclef Jean heads down to Kingston, Jamaica, for the town's reggae and dancehall festivals, like "Overloaded" (held annually in December) and "Fully Loaded" (July), he takes the stage to "battle" with Jamaica's prodigiously talented indigenous M.C.'s. "Kingston plays host to the best soundclashes in all of Jamaica," Wyclef says, "so when I'm there, I know I'm battling with the best." (Call 876-755-4042 for festival information.)

Spa
Makeup queen Cristina Bornstein (she co-owns Tony&Tina) maintains her alignment at Pura Vida Spa in Costa Rica (888-767-7375; www.puravidaspa.com). "You can do yoga, visit a volcano, go white-water rafting, and benefit from om cho, a Tibetan massage technique traditionally taught only to blind men," she says.

Nude Beach
"Nude sunbathing is the best way to feel the sun, the wind, and the water without being stuffed into hot, sticky Lycra," says Judi Ditzler, editor of Nude & Natural magazine and a member of the Naturist Society. Club Orient (590-87-33-85), on the French side of St. Martin, is her personal favorite. "Orient has that free-spirit island feel combined with a unique European flavor. You can't find that on South Beach."

Shopping
Pat Buckley has explored the Caribbean dozens of times with sailor hubby William F., so she knows better than anyone where to find the best island shopping. "You go to St. Martin," she insists. Not St. Barts? Or Puerto Rico? "No, no, no. Listen to me. Go to St. Martin. In Marigot, on the French side of the island, you can get your Chanels, your Manolos. At Christmas, they fly in the most marvelous foods. Foie gras — whatever you want. It's St. Martin. Hands down."

Socialite-spotting
Hotelier Jeff Klein — pal of Alexandra von Furstenberg and Lulu de Kwiatkowski — is opening his City Club Hotel in Manhattan this winter. He's usually secretive about the getaways of his friends, but he still happily names a few of their haunts: "Mustique and Careyes, Mexico, are always chic, and you won't get the couple with their screaming kids. I love kids, but come on. It's all about getting a massage at sunset."

Honeymoon
Plotting out nuptials for Tom Clancy, various Rockefellers, and Kyra Sedgwick keeps wedding planner Marcy Blum with her finger on the haute honeymooner's pulse. "Last year, there were two destinations: Bali and the Amalfi coast," she says. "But now everyone is going to the Caribbean. Jamaica, Antigua, the Bahamas." She recommends Sandals Royal Bahamian (242-327-6400) and the intimate Small Treasures properties in the Bahamas (www.smalltreasures.bahamas.com). "There was a trend away from just lying on the beach. But now people are traumatized and are returning to old-fashioned, relaxing honeymoons."

Bed & Breakfast
When British handbag designer Lulu Guinness is looking for inspiration, she heads to Florence and the Residenza dei Pucci: "There are incredibly comfortable beds and lots of chintz fabrics. It only has eight rooms and is perfectly located only 50 paces from the Duomo." After visiting the Uffizi and stopping by the Santa Maria Novella perfumery (which inspired her Perfume bag), she hits Zibibbo in Via di Terzollina for dinner. "The menu is different every night."

Cheese Store
Where does Artisanal's fromagier, Peter Kindel, go when he needs a quick fix of the stinky stuff? "Paris," he responds. "Without a doubt." Kindel goes to Barthelemy in the Seventh Arrondissement. "They have Vacherin Mont d'Or — the biggest cheese to get in France right now. I'm a cheese-o-phile and a Francophile, so it's perfect!"