@dke - yes, plenty of folks we know who own family cabins in the mountains in NC. When they retire, they summer there.
@MaineLonghorn - 80° is my ideal temperature!! I am freezing if the temps get much below 70°. In the summers, it is cooler (relatively speaking) at the beach than it is inland. Beach breeze helps. But, I would much rather be hot than cold.
It’s wonderful to live in a country that has so much diversity of climate, vistas, and lifestyles. Something for everyone!
We have a timeshare in Grand Cayman. There are several people who have 6-8 weeks and they spend Much of winter down there.
When we were at Turks and Caicos there were several snowbirds there also. It seemed like they had pretty small condos for winter, and they would go home if they needed medical care, for example (this is pre-COVID).
AMEN! H and I have had people comment on our choice but we are not hot weather people. WE would be miserable year round in a place like Florida.
HI is our dream snowbird place too. We absolutely love it there, esp on Kauai (beauty) or the Big Island (diving + volcano).
The con is it’s so far away from everything and everyone else. At least in the Caribbean it’s a short flight away from some islands - and a boat ride away for many of them (esp nice for sailing-lover H).
From what I’ve heard, a big con of HI is high cost of living (especially if you want to buy a place).
Has he thought about ice sailing? 
My sister-in-law has a place in Costa Rica. Her area gets a lot of snowbirds from Canada. People rent but they come back year after year developing a community. I’ve heard the same for those who do winter rentals in Palm Springs area.
Too late. I’m here in Florida, though it has been unseasonably cool for the last few days.
My in-laws began coming to Florida every winter (largely because I didn’t feel like spending winter holidays up in Canada). First for 3 weeks then a month and now to 5 months. Because of that, they got to know people and build a community. My FIL died, but my MIL knows quite a few people. She then had a partner and he would come down. He has now died and she has slowed down a lot so is seeing people a lot less. But her family is coming down to enjoy the weather and take care of her.
He said he’s seen it, but the cold doesn’t appeal to him. Right now he’s quite pleased that two of our boys are next to Great Lakes and the other is in the Caribbean. We might not need a place of our own. We may be able just to set up shop seasonally in their basements. 
I still want to try it. Just need to find an opportunity.
Best boat is one a friend owns. Just like a pool. 
H just owns a small, antique racer right now - one he got for free and restored. (Lightning) He loves his baby and gets a lot of positive comments from people about it.
One of the funniest things is one of my guys was making a video about plants and someone commenting said something to the effect of, “Sorry to go off track, but is that a LIGHTNING behind you???” Son took it in good stride and told him about the boat, etc, but he made sure to check his background before making videos afterward.
Don’t come to San Diego because…hmmm…ummm…
Got it! There really are bugs here and it does rain in the winter. Although we are finishing the driest January since 2014.
And there’s marine layer at the coast in the late spring and early summer.
I learned to sail in a Lightening, so don’t go calling them antiques!
One thing to consider as well (especially as we age) is medical care. Sadly, HI is short of specialists, especially on all islands other than Oahu. If you’re pretty healthy, it may not be an issue but as we age, things do pop up and flying for medical care isn’t all that fun, though I’ve been doing it for >20 years.
My DIL was born and grew up in HI. They left when her mother got ill and they tired of her having to fly to other islands for treatment.
Some of the docs fly to treat neighbor island patients but that seems likely tougher to schedule. I have local MDs on Oahu plus have flown to see my specialists in Denver and SF and Palo Alto. With telehealth and ability to see my local MDs, I’ve made it work but if I needed more care, it would be challenging.
I’m loving all the snowbird discussions and the opportunities for establishing communities. I was frankly all set to plan a future out west where my kids are located - hub’s desire for warm weather has made me rethink that as a singular destination.
I’m hopeful in the next year we can try out some of these warm spots! A family member has a timeshare in Mexico - I’m thinking renting near family can be another way of setting roots/establishing a network in a part-time place!
Good point raised about potentially transitioning to the warm, part-time place full-time, down the road (and whether there is the medical infrastructure to support that!).
Yes, medical professionals and good specialist are important to me, as I’ve seen the difference between outstanding medical care and so-so or worse care. We have traveled for my care and for our kids’ care. It was well worth it to us.
This is what we’ve been doing for a few winters now, taking a “break” and going to our usual spot in FL last year during Covid (and a few years while we were paying for college - hence - becoming “the office workers”). I gotta say, testing these places out in Feb is rough, really, really rough when it’s 29 degrees out and pretty brown looking outside as we get ready to leave. 
If we buy, it’ll probably be in a year or two, but first we need to find a spot that appeals to us enough to want to return there a bit. So far, we’ve enjoyed visits, but other than HI, we’re more interested in seeing what else is around.
It might be that “we” are better renters than owners due to our love of wandering and seeing new places vs wanting a place to settle down. If my body could handle sailing, H would be spot on thinking we’d enjoy a liveaboard sailboat. Alas, I prefer scuba and snorkeling to sailing.
It’s so hard to decide where to move for “retirement.” After I sold my company 13 years ago we jumped into the relo game for DH. We moved 4 times since then. Our parents stayed in our hometown until we were ready to find our final destination. My parents moved here last year and MIL is considering it as well. All of our siblings are still in the relo game, so we’re the only ones who hopefully won’t move again. We figure DD may end up in the same situation. That’s one of the reasons we picked upstate SC because we figured she’d come back to Clemson for games, reunions, etc. Bonus was it was a vacation/retirement spot, so lots of amenities. We really considered the beach instead of Lake Keowee, but figured with the $ we’d save we’d we could go to the Caribbean for vacay 