Well if I'm single, I probably go to the place that I think has the most women that fit into my type. It would definitely be fun for a few years, but I probably wouldn't have much to show for it when it's all said and done, because those places ain't cheap, and I'm sure I'd be spending a lot on entertainment too in addition to the cost of living price tag.
But if I'm smart, I forget about any kind of enjoyment now, and focus on my retirement plan. Go to the place with the cheapest cost of living. Maybe move in with my folks. You can retire before 40, then it's all vacation after that. Financial Independence is definitely an achievable dream, read up on it, a lot of stories out there of people who successfully achieved it.
If you'll be making the same $100k+ salary wherever you go, assuming you live in a place l like Boston now, you'd be taking a pay cut to move to NYC or San Francisco or Hawaii, probably a lateral move to LA or San Diego or Alaska, but you'd be getting a nice lift in Miami and Vegas(
at least according to the Cost of Living calculator I'm playing with online right now), but I'd imagine entertainment eating up all my savings in those places. Places like Dallas, San Antonio, Austin, Charlotte, Charleston, Denver, Atlanta, Nashville, etc. would probably be nice places to live with a lot of things to do, good size singles crowd, and cheap cost of living. Stack as much of that paper while you can, don't spend it all.