It's every serious skier's summer fantasy to make a pilgrimage to Chile, with its intense steeps, untracked powder, and abundant red wine. Book your trip now for the first three weeks in August, after the Chilean July holidays wrap up, leaving the ski areas empty. Start in Portillo—where each season the massive yellow Hotel Portillo hosts an eccentric cast of Brazilian heiresses and Austrian ski racers—and then head south toward the Lake District. Along the way you'll find Nevados de Chillán, where you can ski off-piste powder past hissing, steaming blowholes on an active volcano and tap into the open bowls of Valle Nevado, El Colorado, and La Parva, where hidden gullies shelter powder long after storms. There, if you rent a car, you have the flexibility to do road laps (think DIY cat-skiing). Don't forget the actual snowcat operation at wild, untamed Arpa, a low-key yin to Portillo's luxe yang. For a great introduction to Andes skiing, check out professional skier Chris Davenport's Ski with the Superstars week in Portillo, which features personalized coaching by some of the biggest names in freeskiing, including Mike Douglas, Olympian Wendy Fisher, and Davenport himself ($2,150; steepskiing.com). Admire your lines from the best ski-lunch spot on earth—the deck of Tío Bob's, an old stone shepherd's hut perched on the edge of a rocky ridge surrounded by the jagged Andes.