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Who goes: Kate Hudson, Nicole Richie, the Hilton clan, Dennis Hopper, Stavros Niarchos.
Where to stay: The Four Seasons Resort Maui at Wailea.
Where to eat: Nick’s Fish Market at the Kea Lani, the Hawaii branch of Spago or Haili’imaile General Store for a lilikoi margarita.
What to wear: Free City T-shirts, Puka bead necklaces and a Fred Segal shopping bag—as a beach bag.
What to do: Snorkel in Molokini reef (one of the best in the world) or take a helicopter tour of the island.
Beware: Reserve your poolside cabana at the Four Seasons early—guests have been known to send their nannies down at 4 a.m. to claim a spot.
PALM BEACH, Fla.
Who goes: Woody Allen and Soon-Yi, Vera Wang, Aerin Lauder, Marjorie Gubelmann.
Where to stay: The Breakers, The Colony or Mar-a-Lago if you are an FOT (Friend of Trump).
Where to eat: Chez Jean-Pierre, Daniel Boulud’s joint Cafe Boulud, Amici for lunch, Michael R. McCarty’s for a nightcap.
What to wear: A Lilly Pulitzer one-piece or Vineyard Vines swim trunks, Steven Stolman sweater sets and Stubbs & Wooton velvet slippers—lose the socks.
What to do: Shop along Worth Avenue or take a seaweed bubble bath at the spa at The Breakers.
Beware: Winter weather in the Sunshine State can be iffy.
Who goes: Jemima Khan, Hugh Grant, Sting, Simon Cowell, Cindy Crawford.
Where to stay: The Sandy Lane Hotel.
Where to eat: Enjoy the view from the glamorous Cliff restaurant, try the beachside Tides or get down at Oistin’s Fish Fry.
What to wear: All you need is an Eres bikini.
What to do: Waterski, play golf on Sandy Lane’s three courses or surf the waves at Bathsheba beach.
Beware: The Sandy Lane refuses to serve tap water anywhere on the premises and charges for bottled water.
Who goes: Valentino, Roman Polanski, Ivana Trump, Linda Evangelista, Elle Macpherson, the Khashoggis.
Where to stay: The Gstaad Palace Hotel, your own mountaintop chalet or go Eskimo-style at Iglu-Dorf.
Where to eat: Work up an appetite on the slopes for a seven-course meal at Chesery.
What to wear: Euro ski–chic and a bauble or two from the Cartier or Bulgari boutiques.
What to do: Rub elbows with Roger Moore at the superexclusive Eagle Club (but the wait list is three years long) or hire a guide for snowshoeing.
Beware: Given global warming, there might not be snow on the slopes at the same time you are.
Who goes: Nicole Kidman and Keith Urban, Russell Simmons, Jay-Z and Beyoncé, Paul McCartney, Ron Perelman, Clive Davis, Harvey Weinstein.
Where to stay: A private yacht, one of the 36 private cottages at Eden Rock Hotel or a room at Hotel Le Toiny on the Atlantic side for secluded sunbathing.
Where to eat: Maya’s, which rates with Martha Stewart; La Mandala, or Kiki E Mo for sandwiches and snacks.
What to wear: Calypso bikini bottoms (topless sunbathing is de rigueur), flat sandals to navigate the treacherous roads and an Hermès Birkin bag.
What to do: Hit the nightclub Nikki Beach, the outpost of the Saint-Tropez spot of the same name, or Le Ti St. Barth’s. By day, shop on Rue de la Republique.
Beware: Fresh fish only comes in on Thursday. Keep that in mind when ordering dinner Wednesday night.
Who goes: Goldie Hawn and Kurt Russell, Jack Nicholson, Seal and Heidi Klum.
Where to stay: Little Nell or the Jerome.
Where to eat: Cloud Nine, located halfway up Aspen Highlands; Nobu’s Matsuhisa restaurant,
or new the hot spot Lu Lu Wilson.
What to wear: Aviators on the slopes and Sorrel boots for après-ski—only neophytes wear furry boots or Uggs.
Where to après-ski: The Caribou Club or 39 Degrees, or hear a band at Belly Up.
Beware: At 7,800 feet above sea level, it’s common to suffer from altitude sickness—or to get tipsier than expected.