If you fly privately, you're the type who's most-likely been to Aspen. See this recent, wonderful article from contributor Shelby Hodge, and see why it's called a rich man’s paradise.
If you don’t own your own plane, charter one and head to KASE (the four letter identifier for the Aspen airport). We recently put a family of six on a mid-sized plane from Houston to KASE for a four day weekend for under $30,000. If you live closer, that number would go down. Four couples on a slightly larger plane could run $38,000 – split that four ways, check into the Hotel Jerome and start drinking at the Caribou Club!