By Lindsey Olander
June 26, 2015
Credit: Will Wissman

Upscape (formerly Santiago Adventures) ordinarily specializes in ultra-bespoke journeys, but their first group tour, Ski-In / Wine-Out, is as enticing as any tailored trip. For nine days, serious ski lovers will mountain-hop in the Chilean Andes (think early mornings spent carving the slopes of Valle Nevado, Portillo, Ski Arpa, and Chillán). Craziest moment? Traveling by snowcat up Ski Arpa—the only snowcat ski resortin South America—before descending some 13,000 vertical feet through fresh, untracked power.

Credit: James Florio

Don’t think it can get any better? After hours of high-altitude runs, indulgence awaits in the form of nightly wine tastings at some of the country’s premier vineyards—Viña Errazuriz, in the same family for five generations; the Mingre estate, owned by winemaker Julio Bouchon and known for its Maule Valley reds—before bedding down in local haciendas. Call it the best of both worlds. Tour runs August 1–9, 2015; from $5,995.

Adventure Scale = ***

Lindsey Olander covers adventure at Travel + Leisure. Follow her on Instagram and Twitter at @lindseytravels.

* Child’s play.
** You’ll break a sweat.
*** Heart-pumping happiness!
**** Adrenaline junkie, much?
***** Balls to the wall, envy inducing, nutso.