When do you start planning? (Several years between trips)

The one problem I see with planning too far in advance is planning for stuff not yet done.

I feel sorry for anybody planning for Star Wars: Galaxy's Edge right now. It could open November 1, it could open December 31!

This is why we are waiting for Galaxy Edge and the Guardian's ride and the Spaceship Earth refurb to be done. Those are the three big things we want to see next.
 
I’m about to go on Spring Break, but my daughter wants to go next summer for her senior trip. So currently, we are about 18 months out and we are at the point of trying to narrow down a time frame, resort, and length of stay. We’ve already decide that we want to do park hoppers and dining plan on this trip which are things we rarely do. So it will probably be a shorter stay. Between now and say June first, I’ll be reading trip reports and trying to get a feel for crowd calendars which I realize will be completely skewed once Galaxys Edge opens. Our schools let out mid May, we do might try planning right after school let’s out to hopefully beat some of the summer rush. By June, I hope to be ready to book something tentative. Where we book will have to do with what promotions they are running at the time. Then I’ll start focusing on ADR’s and be ready at 180 days to make those.
 
I also book with a TA that does agency exclusive discounts that come out a year before. So I book our room then. I have an idea of where we would like to stay, I get a few quotes for different resorts and then we decide which hotel to book. We don't really change resorts once we've decided where to stay so it's nice to have our resort booked WITH a discount a year ahead. No waiting for Disney to release discounts. Last trip I also rented DVC points 11 months out so that was a done deal. No changes! That takes a huge load off of me.

Then once that's booked I'm in full planning mode!
 
We went on our first family trip this past October 2018. DS was 5 when we went. We decided we wanted to go again once alot of the new stuff opens and before DS turns 10 so he will still be a Disney kid....pricewise. So most likely we will be going either the summer of 2022 or summer 2023. Starting in January I started a file where I have jotted done some tentative possible plans for our trip.
 

We guesstimate 2021 at the earliest after our trip in June. So once June is over we plan for a different theme park vacation the next year. DD10 is finally at 54" which in the coaster world puts her at riding pretty much everything. Budget wise we plan small theme park vacations on our off Disney years so we can save for future Disney visits. A portion of my paycheck goes towards a vacation account and we budget based on that. With all the OT I've had to do the past year, we should have enough to go for 10days. Usually get a Friday flight and a Sunday flight home, with our work scheduled that burn only 6 vacation days
 












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