Aspen Snowmass

Aspen is chic and cozy with lodges and condominiums nestled right on the slopes. With the average home costing over four million U.S. dollars, Aspen is one of the most upscale ski resorts on the planet and a playground for the wealthy. Aspen is certainly not your run-of-the-mill destination and if you want it ritzy you can have it—rubbing shoulders with showbiz and sport celebrities, many of whom have homes here—but it is also a great ski area. Some come to Aspen just to see and be seen, but skiers and ski-bums in the know are coming here in increasing numbers to test themselves on Highlands, which boasts some incredibly challenging terrain, including spectacular backcountry access.

Skiing in Aspen can be very expensive (if you go five-star) but it can also be affordable. If you’re on a tight budget it is cheaper to stay in Snowmass or Highlands or commute from one of three more modest towns up to half an hour away. And there are the occasional freebies such as complimentary mountain tours, free shuttles between the four mountains, and free coffee and cookies at the base of the mountains.

Aspen itself is a historic Victorian-era town and has restaurants, art galleries, stores and boutiques, along with an opera house, two movie theaters, an ice rink, and a skateboard park.