Vail and Aspen Colorado and Key West Florida are the 3 priciest US destinations per cheaphotels.org. Ever been to any of them?Didja like?

I've been to all of them.  I had fun at each, like I always do.  The fact that they were expensive wasn't the determining fun factor.  It never is.  Thank God I don't carry that chip on your shoulder.

I've gone skiiing at the Vail, CO ski resort. It was very nice.

Otherwise, no, I've never stayed in Aspen, Vail, or Key West.

Key West is fun. I've been there a couple of times with my family.