Ditch summer entirely and head to the Southern Hemisphere, deep in the throes of austral winter. An overnight flight to Santiago, Chile, plus a two-hour drive will land you high in the Andes at Portillo ski resort, one of the country’s top winter draws. The Grand Hotel Portillo, looking spruce after a major makeover, abuts a frozen lake and offers ski lifts to terrain that ranges from scenic groomed runs to extreme couloirs. If you want to up the stakes, book a heli-skiing trip. Après-ski, slump gratefully into the hotel’s lakeside hot tubs or pool—it may the only time you’ll appreciate a heated swim in August.