Well.....since someone else is paying.....Hawaii is an obvious choice. Spend some time on Oahu —Honolulu for some city activity, Waikiki beach, and Pearl Harbor for the tours.
Then puddle jump to Maui for super relaxing times, LaHaina, snorkeling and drive up to Haleakala. 5000 would pay for a lot of activity and some damn nice hotels.
My 1st thought was Hawaii,
My wife's uncle did 2 weeks in Italy maybe 2 or 3 years ago and said they WILL go back, but I doubt thats in the $5k or less budget
I personally would love to see Greece,or Italy, Switzerland , Ireland etc etc etc.
But wife doesn't like to fly so getting her on that long of a flight is near impossible
