Almost nothing about Portillo is conventional. There is no town, no condos, no day pass: you book a week at Hotel Portillo, you ski Saturday to Saturday, and you share the mountain with around 450 other guests. The drive from Santiago takes roughly two hours up through fruit valleys and into the Los Libertadores tunnel that crosses into Argentina, with the resort appearing just before the border, framed by the jagged Aconcagua range. The 1966 Alpine World Championships, the only ones ever held in the Southern Hemisphere, gave Portillo runs like Roca Jack, Garganta and Plateau, still legendary today for their steep, sustained pitch and the quirky Va et Vient slingshot lifts that fire skiers up impossibly tight couloirs. The US, Austrian and other national ski teams come for July-August summer training, which means you often share lifts with Olympians. Beyond the lift-served terrain lies a vast playground of high alpine ridges and powder bowls. Evenings are unmistakably retro: cocktails in the Bar de la Cumbre, four-course dinners in the dining room, movies and dancing at the disco. There is no other ski week quite like it on Earth.