First Timer Help

Your target trip is Fall 2026. For September 2026 for example you would book October 2025 for it.

You would use points that at in the UY covering that trip. (If have a June UY, it is 2026 points. If you have a December UY, it is 2025 points.)

Also you look at how many points you have that can be banked from the prior UY or borrowed from the next for the reservation.
When I bought I thought I wanted Oct use year because I do t want to go when Orlando is on fire. I settled for September because the contract was kind of what I wanted. Turns out I am happy with that and have a trip booked for the end of Sept which is the cheapest time to use DVC points. Nevermind Orlando will still be on fire.
 
For your UY, you've identified the months you are MOST LIKELY to travel to WDW - September and mid-summer (I'll just say July and August for that). That is part of picking the best UY. To pick the best UY for you, you also need to consider the months you are LEAST LIKELY to travel to WDW. You want those months to come just before your UY begins.

So, if you think you will almost never travel during November and December, then I'd probably look at a February UY.

If you think you might want to travel around the holidays or the winter months, but you're definitely not going in late spring (April/May), then you might want to look for a June UY.

What you want to avoid is (1) ever having to cancel within 30 days of a reservation no matter your UY, or (2) canceling a reservation in the last 3 months of your UY, but even with 30+ days notice. If you do #1, no matter when, those points go into "holding." If you do #2, they won't go into holding, but you will only have to the end of that UY to use them or lose them which can be as bad or worse than points going into holding.
 















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