Congratulations on the empty nest, Lisa!
We've been pondering the relocation dilemma for two years now. We had hoped to be in SoWal (or close by), but here we still are.
We have one kid who just graduated from college, and another who has two more years in high school--but if the right job came up, we would not be hanging around here. Colorado is really changing and it's not for the better.
After many landlocked years, the water beckons us. I lived on both coasts before moving to Denver and miss the ocean. And I am sick of shoveling snow.
We loved Hawaii (esp Kauai), but there are social issues there and yes, it is far away. One friend of ours built a condo in Playa del Carmen, another is interested in both Belize as well as Costa Rica. I loved Guatemala, but only as a place to visit.
If our kid settles in Europe or anywhere else, we'll visit there, but I am not interested in aging in a non-USA location.
Sarasota is very nice, "but it's full of old people," says my husband.

We like the Keys, were just there in February, and they 'felt' right, don't know how to describe it.
We have looked into the Carolinas as well.
I like the big boat/little boat idea.
Spouse wants out of Denver. We shall see what shakes out.