Mohonk Mountain House New Paltz; 800/772-6646 or 845/255-1000, fax 845/256-2100; www.mohonk.com; doubles from $310; kids 4—12 $70, over 12 $115 (all meals included). THE SETUP A seven-story Victorian pile on a lakeside cliff, with about half of its 261 rooms overlooking the water, plus six cabins that sleep up to six people each. GENES MATTER The Smiley family—could there be a more appealing name for hotelkeepers?—have owned this lavishly landscaped perch since 1869. They cater to reunions with their Victorian dining rooms, kids' programs even for two-year-olds, and weekend themes appropriate to family ancestries—if you're of Scottish descent, say, you can gather in January to study bagpiping and kilt-making.
Guadalupe River Ranch Boerne; 800/460-2005 or 830/537-4837, fax 830/537-5249; www.guadaluperiverranch.com; doubles from $299; kids 5—12 $45, 13—17 $65, 18 and over $85 (all meals included). THE SETUP Cut-stone cottages in the woods plus river- or canyon-view rooms and suites (46 units total), on an estate that belonged to Olivia de Havilland. THERE'S EVEN A SPA Form flotillas of inner tubes to ride the sleepy Guadalupe River. Send your party's adults for sea-salt polishes at the spa, while the kids check out a doe that lives improbably among the longhorn cattle: the herd raised it after it was orphaned, and it stays even though it could easily jump the fences now. As a souvenir, give everyone jars of barbecue sauce made from the ranch's prickly pears.
GOOD DEAL: Wildflower Inn Lyndonville; 800/627-8310 or 802/626-8310, fax 802/626-3039; www.wildflowerinn.com; doubles from $150; kids 4—11 $20, 12 and over $25 (breakfast included). THE SETUP A Federal farmhouse and outbuildings, many in Vermontian red, with 21 suites or rooms. THE TICKET FOR YOUNG FAMILIES The owners know it's important to serve pancakes shaped like teddy bears, as well as early kids' dinners followed by G movies (during which adults get to linger over filet mignon or cognac-soaked breast of duck). Parents and offspring can swim together in the granite-edged pool in summer; in winter, sled down the inn's hill or play broom hockey on its pond.
GOOD DEAL: Beach Haven Resort Eastsound Eastsound; 360/376-2288, fax 360/376-6183; www.beach-haven.com; cabins or apartments from $95; one-week minimum in summer, two- or three-night minimum the rest of the year. THE SETUP A strip of pebbly beachfront and centuries-old pine forest, with 13 log cabins and two modern apartments, all kitchen-equipped, accommodating up to 10 people per unit. LOOK FOR THE HOLE Summer returnees tend to book the following year's visits as they're leaving, so consider gathering for spring break or Thanksgiving—the Puget Sound's year-round attractions include sea kayaking, watching pods of orca whales, crab trapping, and peering into tide pools of sea anemones and starfish.
Red Rock Ranch Kelly; 307/733-6288, fax 307/733-6287; www.theredrockranch.com; $1,585 per person for six nights; six and under half price (all meals, activities, and gratuities included). THE SETUP A ranch with nine log cabins of up to three bedrooms each. The ranch owns the valley floor, surrounded by national wilderness. CALLING ALL COWBOYS Fish for cutthroat trout in the ranch's creek, sip coffee boiled over open flames at a riverbed cookout, and hike or ride to take in views of three mountain ranges. Your group's seasoned horsepeople should know, though, that they can rarely gallop at the ranch—saddle time is spent mostly in the steep wilderness, where the horses can't rush and must concentrate on every hoof-hold.
The Buccaneer Gallows Bay, St. Croix, U.S.V.I.; 800/255-3881 or 340/773-2100, fax 340/778-8215; www.thebuccaneer.com; doubles from $195; kids under 18 free in summer, kids 12 and under $10 in winter (breakfast included). THE SETUP A plantation house and pastel outbuildings (many with connecting suites), totaling 138 units, plus an 18-hole golf course, owned for five decades by a family that's lived on St. Croix since 1723. IF ANYONE CARES TO BUDGE FROM POOLSIDE Take free lessons in snorkeling, sailing, or kayaking. Encourage the 4-to-12 set to hunt for geckos in the free kids' program.
Dragon Bay Port Antonio, Jamaica; 877/677-3724 or 876/993-8751, fax 876/993-8971; www.dragonbay.com; one-bedroom suites from $210; kids 12 and under free, over 12 $20. THE SETUP Thirty villas climbing a lagoon bank, with décor that combines tropical prints with such neo-British colonialisms as a half-timbered pub. SIGHTSEEING WITH A HOLLYWOOD THEME Lord of the Flies and Robin Williams's Club Paradise were filmed on these white sands, the real Blue Lagoon is nearby, and Tom Cruise made Cocktail at the resort's thatched-roof beachfront watering spot—now known as the Cruise Bar.
GOOD DEAL: Maho Bay Camps/Harmony Studios St. John, U.S.V.I.; 800/392-9004 or 340/776-6240, fax 212/861-6210; www.mahobay.com; doubles from $75; kids under 16 free, over 16 $12; minimum one-week stay in winter. THE SETUP A solar- and wind-powered eco-compound of 114 "tent-cottages" (canvas-wrapped wooden frames) plus a dozen cabins built from recyclables, alighted as gently as tree houses on steep terrain. A FEW INDULGENCES You can view lava-red sunsets, snorkel through neon-hued fish schools, and hike to ruined sugar mills. But you'll also have to take showers (brrr) in communal bathhouses (unless you have a cabin), fill drinking-water jugs from communal taps, and cook on propane stoves—or you can dine at posh Caneel Bay down the road, or at Maho's own restaurant, self-serve, of course.
GOOD DEAL: Nail Bay Virgin Gorda, B.V.I.; 800/871-3551 or 284/494-8000, fax 284/495-5875; www.nailbay.com; rooms from $99 off-season, suites from $135, villas from $176; kids $30. THE SETUP A year-old spread of two apartment houses and 16 privately owned and diversely decorated villas, with up to five bedrooms apiece. PLAY HOUSE Pretend you've all managed to agree at last on buying one grand family compound. Roam from villa to villa, dipping into each other's private pools and ogling each other's architecture (one house even comes with a waterfall in its living room). Break from the clannish insularity over West Indian barbecue at the resort's restaurant, or sip drinks from the swim-up bar.
Peter Island, B.V.I.; 800/346-4451 or 284/495-2000, fax 770/476-4979; www.peterisland.com; doubles from $490 in summer; villas from $870; children under 12 $75 (all meals included). THE SETUP Fifty-two bungalow-like rooms, plus two villas on a squiggle of an island off Tortola on which almost nothing else has been built. WHY YOU'LL TEAR YOURSELF AWAY FROM THE BIKE AND BOAT SUPPLY For a trip to the island's tallest ridge. At 1,000 feet, it offers one of the Caribbean's finest vistas—a dramatic backdrop for that family photo.
The Club Med Alternative
For privacy, you might be able to do better. It's not the perfect ticket for a grand cultural excursion, either. But for family fun by the minute and, most important, ease, look no further. The majority of Club Med's 127 villages worldwide (800/258-2633, www.clubmed.com)—whether the sun-worshiping spots in the Caribbean, Mexico, Brazil, Asia, Australia, and on the Mediterranean coast, or the ski resorts in the Rockies (a new outpost just opened at Crested Butte, Colorado) and the Alps—welcome multigenerational gatherings. And the kids' program lasts all day.