Some stories:
My grandparents retired at 60 and 61, with full-pensions. They had previously used the few weeks a year my grandfather had off from work as a machinist to travel, typically via a conversion van, but sometimes even in a car. My grandmother was a teacher, so some summers she'd travel by herself, and some summer she'd do the great American road trip. By the time that they were in the 40's they had visited nearly every state in the lower 48. In their 50's they headed for Alaska. In retirement, they didn't get enough and lived the RV life for 12 years. All the while living in York County, PA, in the same home they had owned for 35 years.
Luckily, my father and his brothers stayed local. Our family didn't leave Pennsylvania. Hell, very few of the family traveled at all.
My father and uncle are both gone, leaving my grandparents youngest son as "the decider." He pretty much determines where they will live. Unfortunately, he has decided that Florida is his new state of mind, and has brought my grandparents with him. This, to their chagrin, is not as enjoyable as they might have hoped. All his life he felt stuck in Pennsylvania, and while we all supported his moving, the rest of his life wasn't ready to go with him (including wife, kids, etc.)
My grandmother says "I would have enjoyed living in Florida when I was in my 60's, and had 20 years to make friends, now I just feel like an outsider, torn away from home, my relatives, my friends...what few were still living." She's pretty depressed because she's outlived many of her friends, her siblings, her sons. She wanted her last remaining son to be happy, and his happiness is moving his family to live where he lives (in Florida.)
My parents and in-laws are similar but different situations. My parents, in their early 70's, are watching younger friends run off and do the "late career jump" where you follow the money in order to ramp up the social security perks. My parents will never be able to afford living multiple places, but in their case, unlike my grandparents, they have nothing to lose. Family is dwindling, and friends (and me) are starting someplace new.
Surprisingly, my parents are considering living in Costa Rica for 1-2 months next year. This is very much unlike my parents. Their reason? An excuse to experience new things and meet new people. Not to live permanently, just to have stories to share with friends back home.
My in-laws, can't bear to leave family behind, despite the fact that they always intended to retire in style. It becomes increasingly worrisome how fragile her parents are becoming. They've got all the money, but none of the desire to leave a place their kinda unhappy with. The opposite of my parents.
We have some friends and former neighbors who did it right. When the parents retired, they basically committed to following their kids, and their families, where-ever. When the kids went to Phoenix, they bought a house in Phoenix. When the kids came home, they bought a house down the street. I think it has made their family stronger, even after the grandfathers on both sides of the family died.
All of this has made me want a "Mother In Law Suite" more and more. I value my new life in the desert Southwest, and I don't want to leave it, but at the same time, I wish my family, and my in-laws could live more comfortable with us, for longer lengths of time.
When you're retired, you can visit your kids, friends and family as long as you are welcome. Your kids can't say the same with todays limited vacation time. Eventually you get to an age where you've gotta plant yourself. Starting making connections in that place today, so 20 years from now it's the place you'll want to die. Something to think about.