WHERE Grand Cayman
WHY The Ritz-Carlton drafted the equivalent of the NBA Dream Team for its new Grand Cayman resort, scheduled to debut this month. The starting lineup: celebrity chef Eric Ripert, opening two restaurants (one formal, one casual); champion golfer Greg Norman, designing an environmentally sensitive nine-hole course along a saltwater lagoon; explorer Jean-Michel Cousteau, running an aquatic education program; and legendary tennis coach Nick Bollettieri, presiding over the courts. As if that weren't enough, La Prairie was also brought in to create a 20,000-square-foot spa—one of the largest in the Caribbean—featuring treatments inspired by the tropical setting.
HOW Seven Mile Beach; 800/241-3333 or 345/943-9000; www.ritzcarlton.com; doubles from $699.
WHY Celebrate three holidays in one aboard the Crystal Serenity. The special 14-day cruise departs December 21, sailing round-trip from Los Angeles to Mexico's Paciﬁc coast with stops in Cabo San Lucas, Puerto Vallarta, Mazatlán, and La Paz. The itinerary incorporates a wide range of festivities and adventures—from a Hanukkah dinner (complete with latkes and matzoh-ball soup) and Christmas-tree lighting, to a zip-line adventure in the Sierra Madre mountains, to a Bloody Mary brunch on New Year's Day.
HOW 800/804-1500; www.crystalcruises.com; from $6,245 per person, all-inclusive.
WHERE Southern Maine Coast
WHY York Beach is even more atmospheric off-season—its deserted boardwalks, shuttered arcades, and often misty shores are perfect (albeit chilly) for walks in the salty air, with only intrepid seagulls for company. Just down the shore, the historic Cape Neddick lighthouse is at its most photogenic, shrouded in snow; in nearby Kennebunkport, Santa Claus arrives by lobster boat during the annual Christmas Prelude (December 111). Warm your beachcombing toes before a ﬂagstone fireplace in one of the three Arts & Craftsstyle Wharf Cottages at the White Barn Inn.
HOW 37 Beach Ave., Kennebunkport; 207/967-2321; whitebarninn.com; cottages from $525.
WHERE Paradise Island
WHY Watching movies from a beach chair just might be the perfect antidote to the winter blues. Designed for cinéastes and snowbirds alike, the Bahamas International Film Festival (December 811) showcases more than 50 films from around the world, including features, shorts, and documentaries, with a special category for Caribbean productions. Screenings of films such as the underwater documentary Deep Blue and Turtles Can Fly, an Iraqi war drama, take place not only in theaters but also, after sunset, on the sand. Plus, director Spike Lee will be in attendance as this year's honoree for career achievement.
HOW www.bintlfilmfest.com. Atlantis, Paradise Island Resort, 888/528-7155 or 242/363-3000; www.atlantis.com; doubles from $270.
WHERE Ambergris Cay, Belize
WHY Get away from it all at Azul, a secluded, two-villa beach resort opened this year by a pair of expats from San Francisco. Located six miles north of San Pedro on one of the island's most idyllic stretches of sand, the property's meticulously crafted open-plan villas combine modern perks (plasma TV's, Viking kitchens) with rustic design elements (bamboo railings, cabinets carved from ziricote wood). Take a dip in the rooftop hot tub overlooking the jungle and use the old-school walkie-talkies to summon frozen mojitos from Rojo Lounge, Azul's beach bar.
HOW North Beach, San Pedro, Ambergris Cay; 011-501/226-4012; www.azulbelize.com; doubles from $695.