These days, the resort's offerings are enjoyed by three generations of Flynns: Donal, a retired television executive; his wife, Joyce, a former soap-opera actress; their grown daughters, Nancy Flynn and Kathryn Flynn Michaels; Kathryn's husband, Lawrence; and the Michaelses' daughter, Serena, five. When the Flynns aren't snorkeling over coral reefs off Grotto Beach or swimming and snacking at the open-air grill on Mermaid Beach, they like to collect shells on remote Whistle Beach, with its craggy cliffs, big waves, and pelicans nesting on a high promontory. "Basically, we live in bathing suits and beach robes," Joyce says.
The resort was founded 55 years ago, and in the old days, guests—referred to as continentals—came for the whole winter and hunted boar on the property. Bringing children wasn't allowed. Today the Buccaneer is extremely family-oriented and has an all-day kids' program. Serena's favorite activity, though, isn't on the schedule; it's simply having breakfast on the great house terrace and leaving trails of sugar for lizards and bananaquits, the black-and-yellow birds that come to call.
The Flynns always look forward to the rollicking cocktail party held for guests on Tuesday nights in the original stone sugar mill. There's a steel-drum band, rum punch, and Mocko Jumbies, dancers who dress in vivid feathered and beaded costumes and leap about on stilts—a centuries-old island tradition by way of West Africa.
Many evenings the family heads out by rental car to explore the island's restaurants (Kathryn recommends West Indian barbecue night at the Mermaid). They'll also leave the resort for a kayak adventure on the Salt River, where Christopher Columbus once landed, or a catamaran jaunt to Buck Island, an underwater national park, where they snorkel past parrot fish and brain coral (it's labeled). And they're not above stopping at Mont Pelier Domino Club, a bar with a beer-drinking pig. But on Christmas morning, the great house, where Santa hands out presents, is the place to be. "In the afternoon, the steel-drum band plays on the beach," Joyce says. "Music wafts over the water, and we have sandwiches under the palms."
800/255-3881; www.thebuccaneer.com; family suites from $500.
WHO The Schroeder Family
WHERE Vista Verde Ranch, Steamboat Springs, Colorado
YEARS GOING 10
Not one for lazy pleasures, Kihm Schroeder, a telecommunications specialist from Austin, Texas, doesn't like beaches or cruises, or even sitting through a movie. "But if you wake him in the middle of the night and tell him it's snowing, he'll put skis right on," says his wife, Tricia, a former kindergarten teacher.
Back in the early nineties, the Schroeders began searching for a snowy Christmas vacation spot where Kihm (it's an old German name) could ski his heart out and the rest of this sporty family—Tricia, son Jared, 25, and daughters Erin, 21, and Amanda, 15—could do as they pleased. In 1993 Kihm and the kids made a trial visit to Vista Verde Ranch in the Colorado Rockies, 25 miles north of Steamboat Springs. The family hasn't missed a year since.
The big draw in winter is off-trail cross-countryskiing. But the Schroeders are also smitten with the ranch's good-natured staff; its sophisticated local fare (think pepper-seared venison loin topped with poached pears, blue cheese, and a port-wine demi-glace); and its packed program of igloo-building, ice-climbing, dogsledding, and hot-air ballooning so high you can see Wyoming.
The Schroeders stay in one of nine hand-hewn log cabins with wood-burning stoves and doughy down comforters. Upon arrival, Tricia takes a walk around the property to catch up with returning families and staff. Kihm and the kids waste no time strapping on skis. Soon they're up to their knees in powder, revisiting silvery aspen groves and alpine lakes. Elk, snowshoe hares, ermines, and ptarmigan (those grouse-like birds that turn miraculously white in winter) make cameo appearances.
The family sets aside a day to go skiing together, and after dinner all of them enjoy the sing-alongs led by two madcap musicians in the lodge. The rest of the time, Kihm and the kids are apt to be exploring the backcountry while Tricia reads in the hot tub on their porch, rides horses, or cross-country skis on groomed trails.
One year, the Schroeders arrived before Christmas and joined staff and other guests snowshoeing into the forest to cut down a fir tree, which they brought back to the ranch to decorate withcranberry garlands they'd made the night before. But the family's enduring tradition is to head to Vista Verde a few days after Santa's big night. That way, they don't miss the New Year's Eve dinner, when everyone skis or rides on a horse-drawn sleigh from cabin to cabin for appetizers such as salmon tartare "ice cream cones," served with champagne by candlelight. Final stop: the main lodge for an opulent dinner. En route, caroling and plumes of white breath fill the night.
800/526-7433; www.vistaverde.com; cabins from $1,200 per person for a three-night stay, including meals, ski rentals, and ranch activities.