With four mountains on a single lift ticket and a classic ski town — as well as more than a few Hollywood starlets — it's hard to go wrong in Aspen. Aspen Mountain rises straight up from downtown and has a "First Tracks" program, which lets you sign up to get first crack at the slopes. If steep bumps are your thing, head to Bell Mountain; more forgiving terrain can be found at Buttermilk Mountain or Snowmass. When the lifts stop running, head to the Aspen Brewing Company, where you can sample microbrews as well as meet some locals who just might end up showing you the goods on the mountain the next day. The Red Onion Bar and J-Bar both have been around for more than a century — the kind of authentic ski-town bars that hardly exist anymore.
Best For: The buddy trip.