Do you ever stay long enough to where you feel done?

Anything past 5 days and I'm ready to go.

But I live in FL and it's a 3 hr drive for me so that has a lot to do with it as I know I'll be back soon. If I had to fly and deal with all of that I'd probably have a different take.
 
Prior to retirement, my longest visit was 9 nights on one trip. I also did up to 4 trips to WDW each year and also spent time at DHHIR and VB (own at both). First visit was 1988 so a lot of trips since then.

On some trips I was 'done' after 3 or 4 nights, depending on who I was with. On most it was time to go because of responsibilities at home and work. My shortest trips were for 3 nights.

Back then the dream was to buy more points and spend a couple of months in Florida, including an offsite rental. As time passed things changed. I retired in 2018. Prior to Covid I had an option to stay in a relative's short time rental in Reunion. I stayed there a couple of times with family and it was really nice. But overall, I prefer the bubble.

So, also as time went on the months I want to visit have changed. Right now it's November through March. This year I have 3 trips booked, November, December, Late January into Early February. And that's enough.

My kids grew up, got married and have babies. Grandchildren! Now I want to be home at Xmas and NY's, for birthdays and special occasions. Immediate family will come on some trips, but mostly I'll be with a friend or two or I'll be solo.

Things change but I'm still going. I'm rarely bored, always have passes, and never feel compelled to go to a park, I just go when I feel like it. I also go other places, such as Universal, Seaworld, just not recently, but may go again when someone wants to. There are 2 coasts and I like to walk on a beach. I love Florida's state parks. I always try to get to a strawberry festival every few years. I try to see Manatees in the wild when they come up the rivers during cold spells. Haven't been to Kennedy SC in a while, I'm thinking it may be time for a visit. And then there are the birds, I love birds, and I'm the nut with the camera at daybreak and coffee in hand.

Anyway, Disney is in my life but I like to balance things. I'll never exactly be done on any trip because I know I'll always plan to be back. At least until 2042, lol.
 

I wouldn't have any particular time limit, though my stays are rarely longer than 5 nights since I've been a DVC member. That's mostly due to my work vacation time limits - I get 4 weeks a year, so I try to spread it out to include 4 or 5 trips to Disney and one international vacation or cruise of 7-14 days. By wrapping the Disney trips around weekends, I only need to take off 2 or 3 vacation days each trip and can get a 4 or 5 night stay. I go roughly every 3 months or so, so I'm there often enough that anything I 'miss' on one trip I just shift to my next trip. My DIsney trips are my little de-compressions from work - I'm not there to rope-drop, rush from ride to ride, etc...so I don't really suffer any burn-out or feel I've done it all and want to head home. I may choose to spend some time not going to parks, touring resorts, sleeping in late and cooking breakfast in the room, starting the parks in the later afternoon and then transitioning into night entertainment at bars or music spots. I ride a lot of boat transportation because I find it so relaxing. And sometimes, I even do a little work while up there since I can remote in, do a Zoom meet, or call a client if I really need to.

Of course, I don't have any pressures about leaving warm, sunny Florida when I leave Disney, since I live in warm, sunny South Florida - so the weather's usually the same at home as at Disney - if anything, Disney gets a little cooler than we do, so on trips in December through March, I'm hoping to experience some cooler nights that I don't get back home!
 
We had a backlog of timeshare assets from the pandemic closures, and I ended up booking back-to-back weeks at Saratoga with some of them. By the end of that two weeks, I wasn't *done* but I was also rejuvenated enough to go back home.
 
We go for 10 days every March. Rarely go to parks. Just hang out at the pools. I’m usually ready to go home. I’ve been on a few trips where I could stayed much longer. Transatlantic cruises…love those sea days. Africa…incredible. Morocco…would go bs k in a second. And Paris.never enough time.
 
I did once, it wasn't because I did everything I wanted, it was because the cousin I traveled with on that trip was a horrible traveling companion. After the first day, I felt done. 😡
 
We have never managed to do everything. There are experiences that we'd put off due to laziness or time constraints and now those attractions don't exist any more. We have places we like to return every visit and some of those are gone (ESPN) or changed to the point that we no longer enjoy them as much (Rose 'n Crown) and places we've aged out (RnRC). One of the downsides of the pandemic is now all the parks seem so crowded so we tend to just drift away. Shopping isn't as interesting when we've a house full of stuff and know our kids aren't going to want any of it. We're not suited to family trips so I don't put myself thru those any longer. We love the 4D cruise with a WDW night on either end because we get a bit of that excitement to stay at a high point resort and visit places there we've read about.

Over the years we tried different length trips and have come to 5N, 3 times annually, being our sweet spot. After 5 days I really start to miss my own bed and I'm tired of my clothes selection.
 
It’s one of the reasons I love doing 3 to 5 night vacations!!!

Not only at WDW, but for cruises too! Its why I planned my retirement the way I did…instead of a month in January, I will do shorter trips every month!

I’ll hit WDW about 6 times and cruises or other trips the rest! Goal is almost every month!!!
DVC was a life changer.
When we bought our first contract we calculated 7 nights, prob every other year, knowing we would be sad when leaving WDW. This was right before the pandemic.
Now we try to do a Disney weekend of 2-3 days every other month when possible, with Sorcerer passes. (We live in NYC flying into and out of MCO.)

Every trip and every experience is different.
Short answer; No. I do not believe that we will ever feel 'done' with WDW.
 













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