Which resort for which stay?

Queen of the WDW Scene

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Original Poster
In the Parks
For planning purposes let's assume things are mostly back to some kind of normal at Disney for these trips...

My sister and I are planning for 2 trips next year. It would be around the same time they were meant to be this year.
This year the plan was value resorts for both trips and the dining plan for one trip and not the other.
Now that we are not spending the money this year we are thinking about doing club level at CR for one trip and standard room at POP with the dining plan for the other trip.

Now we are just trying to decide which resort for which trip.

The first trip will be arriving in the morning on a Sunday and leaving later in the evening on a Friday. (In August)
The second trip will be arriving later in the evening on a Thursday and leaving in the morning on a Monday. (In November or December)

My thought is that it may be better to stay at POP and get the dining plan for the first trip since it is the more likely trip to offer free dining plus its a bit longer than the second trip so dining experiences can be more relaxing?
Then the second trip stay CL at CR. Save money because its one less night. Enjoy drinks, desserts, and fireworks the first night and mostly just get breakfast the rest of the time, eating QS at the parks since its not as time consuming/costly and we have less park time.

Do you agree that that's the better option or would you do it the opposite and do CL at CR the first trip and POP with dining plan the second trip?

I'm looking for fresh eyes to look at my reasoning lol.


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Your reasoning makes sense to me. Shorter stay with CL, longer stay with dining plan. Love it.


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I agree with your plans from a dining perspective! Also think it would be nicer to be on the monorail line during Nov/Dec assuming you'll want to see Christmas decorations at MK and the nearby resorts.


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I guess it would really depend on exact timing of these trips for me and what discounts you wind up seeing. I'll preface this by saying that we're not DDP fans and will go for a room discount over dining if both are offered. Still, if I'm basing my choices on normal and using 2019 as a gauge...I might be more inclined to go with August for CR when you factor in room cost differences based on time of year and potential savings based on past discounts.

August will be cheaper for lodging than Nov & Dec, regardless of when you go. So, your August rack rate automatically puts you ahead of the game for lodging, no matter where you stay. Based on the rates I'm seeing on Mouseavers for 2021 at the Contemporary, the rack rate difference in these months is significant. You'll also likely see deeper room discounts for August. I don't know what offers you usually qualify for, but if you're a Disney card holder, it was up to 35% off for summer 2019. I don't think room discounts for Nov and Dec 2019 went beyond 20%. I've also seen free DDP in Nov and Dec. It doesn't happen all the time, but it's not out of the question. In fact, we went one Thanksgiving and while room discounts cut out 2 days into our stay, free dining was offered for our check in day. So, it's the one time we opted for it as our discount since it carried through for our entire trip based on how FD works.

So, while it seems logical to pick the more expensive resort for your shorter stay, I think you stand to save more by opting for it on your longer one since it's a slower time where prices are noticeably lower pre-discount.
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