Jackson Hole is home for Tommy Moe. It's where he serves as a ski guide and ambassador for Jackson Hole Mountain Resort. Moe became the first U.S. alpine skier at 23 years old to win two medals in the same Olympics at Lillehammer, Norway: the gold medal in downhill and silver in super G. You and four other buddies can ski all day with Moe for $1,400. Or foot the bill yourself and follow him for seven hours to his favorite personal stashes. He'll even throw in some tips to improve your skiing. Call 800-450-0477 to schedule a ski date.