ITALY (2006 Winner)
Walking the Piedmont
This six-day introduction to the still-quiet agricultural region 40 miles southeast of Turin is a glutton's guide to Italy. Long a gastronomic hot spot (the Slow Food movement began here), Piedmont produces the country's noblest wines—Barolo and Barbaresco—and hearty and refined cuisine like wild boar and risotto with fresh truffles. After daily hikes of six to 15 miles, arrive at a farmhouse ringed with vineyards. When you're not hiking with a naturalist or dining in an award-winning restaurant, taste wines with a local family, sip spumante with a top producer, trail a trifulao (truffle hunter) and his prized dog, or take cooking lessons—then soak in a hot bath enriched with crushed grapes.
Outfitter: Butterfield & Robinson, 800-678-1147, www.butterfield.com
When to Go: May, September
Cycling the French Alps
A ten-day fantasy camp for serious cyclists: Accompanied by a former pro rider/professional photographer, you'll ride stages of the famed Dauphiné-Libéré, contested over many of the same roads as the Tour de France. Ditch the peloton at day's end for elegant digs in picturesque mountain villages such as Uriage-les-Bains, where you'll fortify yourself for the next day's ride with local delicacies like goat sausage from Savoy Alps pastures and flinty white wines. Save your legs for the final 73-mile day (you can also opt for either a 55-mile or 93-mile route)—the Megève-Mont Blanc Classic, with 9,000 feet of climbing over three magnificent cols.
Outfitter: Velo Classic Tours, 212-779-9599, www.veloclassic.com
When to Go: June
Swimming the Coast
Caught in the narrows between Sicily and North Africa, Malta is a group of islands with some of the warmest and clearest waters in the Mediterranean. On this six-day swimfest, you'll self-propel two to three miles a day, hopping from island to island and drying off in small family-run inns. You can always hop aboard the escort boat, but rest assured that your guides know their stuff—many have completed solo crossings of the English Channel. In the evening, the fun continues with talks on swimming technique and video analysis in the hotel pool.
Outfitter: Swim Trek, 011-44-20-8696-6220, www.swimtrek.com
When to Go: April-June, September
Dressage Training and Trail Riding
Difficulty: Easy to Moderate
Saddle sores will be your only worry on this six-day romp through Spain's vast central plateau. HQ is the utterly tranquil El Molino, an 18th-century equestrian center on the fringe of the medieval town of Pedraza. Each morning, saddle up your horse, perhaps a purebred Andalusian, and train in dressage technique. Then take guided afternoon trail rides through the wheat fields and rolling hills of the Castilian countryside, galloping by deep gorges and velvety forests or trotting through Roman ruins. Come evening, you'll dine on tapas, fresh seafood, and el frite—fried lamb with garlic and lemon—accompanied by dry local wines.
Outfitter: Cross Country International, 800-828-8768, www.equestrianvacations.com
When to Go: January-November