November

November for sure!

November or October
 

Regardless of which time frame you pick, do it soon. Rentals having been booking up like crazy! My beautiful 3/2 villa is available 11/16-30th, if you're interested. Rent From A Villager | Home Rentals in The Villages Florida | Advertise Your Village Rental

October is weather transition month
 

October is when the days start getting noticeably shorter, so even though it's till a bit warm, it's still pleasant, not as hot. November is the best Fall month for weather in central Florida so I would personally chose November to come down. And no, you wouldn't be a lousy parent if you were to take a break from the family routine for Thanksgiving for one year.

Usually by November the heat breaks and is way better than October which is still pretty warm. As far as guilt about ditching the family missing one Thanksgiving dinner….they will all survive fine without you. It’s only one day. You will have so much to do in The Villages that getting here the best month is worth it in my opinion.

November, definitely.

Sorry, We are booked.
Serious residents need only apply

We always liked coming in November. But we are here permanently now. Settle on our house in August.

No guilt three. Just tell them if u want to visit for thanksgiving I’m here or I will seep in December

You could always rent a Johnny On The Spot for the week and put it out in your driveway !! ;)

We first visited TV over Thanksgiving 2019... We stayed with friends who had move here that August...

When we told our (adult) daughters (aged 33, 29 and 24 at the time) of our plans, they were mortified! "What will we do for Thanksgiving???", as their mom or grandmothers had hosted every year of their lives...

"You'll figure it out", we told them...

They would up having a "Sisters" Thanksgiving, along with a few roommates and they had a blast. They slept over at my youngest's townhouse for a few nights, and it was a great bonding experience for them...

On our way back home, we stopped by and they fed us turkey sandwiches and other leftovers, just like we'd done for them over the years...

I guess we raised them right...

However, they're still not 100% on board with us moving to TV full time...

Our family loves gathering in TV for holidays. There is something fun for everyone to do. Each family unit rents their own house so everyone has private space and quiet time when needed, and we gather for meals and activities - sometimes all together, sometimes in smaller groups. It works out great. Whoever has the biggest table, most seats, and most dishes hosts the holiday meal, and we all pitch in with the set up, cooking, and clean up.

November

Tell them get on board with us moving here or their place in your will, will be going to the most ridiculous charity you can find. Personally would pick one that benefits left footed frogs.

They say historically April & Oct are the nicest. Last year Oct was very warm and humid. Mid Oct to mid Nov sounds right for us. Seems you've been a responsible caring adult for many years, and as such should be allowed to enjoy the golden years as you see fit. Let your heart make your choices, your kids and grandkids should understand this. If they don't then maybe they don't deserve your love.