So I’ve seen a lot of divisive topics on here as of late. I’m all for open debate and the exchange of ideas, but I thought it might be nice to discuss something fun. So I hope some of you will join in. Here is the question: What is your dream Disney trip? Money is no object. No need to worry about COVID, ADRs, FPs, etc.
Location:
Resort(s):
Number of Days:
Special Event(s):
Who would tag along:
Other Comments:
I’ll start
Location: WDW
Resort(s): Split stay - BLT / BC / AKL
Number of Days: 10
Special Event(s): End of October to hit Halloween and Christmas parties. A VIP Tour!
Who would tag along: DH, DS7, DS4, all my family. Like 30 people.
Other Comments: I would spend some of the time going ride crazy like we do, but I’d take 1-2 days to take it all in. A more relaxing pace. I’d hit up the waterparks, minigolf, Disney Springs, enjoy the resorts more. I’d try out restaurants that I’ve never been to, like California Grill.
Location: WDW
Resort(s): Wilderness Lodge Grand Villa (treehouse?)
Number of Days: 8 nights 9 days
Special Event(s): ?
Who would tag along: The family!
Other Comments: Want a chance to do a more relaxed family trip. 9 days would allow a lot more resort and rest time
Location: WDW
resorts: Split stay AKL Jambo and WL/CC
number of days: well, forever, but in Real Life, 7 each
Special Events: maybe MVMCP but we’re ok if not
Who: DD22, DS26, DS29, DDiL(to be) 29, DH – wish for DGDs and DGSs but not there yet
Tag alongs: I’d love to bring Dsisters and families but they would have to be on board with my planning
Other: My dream is to plan a great stay, and then let everyone in my family go live their Best Disney Life. I want to be part of it, but I want everyone to be happy, with or without me at every moment 
Location: Tokyo DisneySea
Resort(s): Disney Ambassador Hotel
Number of Days: 7
Special Event(s): Disney Halloween
Who would tag along: My Japan loving daughter
Other Comments: I’d love to spend 10 - 14 days doing both Tokyo Disneyland & DisneySea since they are so easy to access in one trip. However, if I’m only doing one Disney park in the whole world it has to be DisneySea!! It takes Disney to another level in every way!
Oowwww, I feel like we get to kinda plan a trip!
Location: WDW
Resort(s): AK, BW, and Poly
Number of Days: 8
Special Event(s): Halloween Party!
Who would tag along: DH
Other Comments: Id love to just have extra days to do half days at the park and lounge around at the resorts some. Would want to try ALL the TS restaurants and Dinner Shows of interest.
Resort: BLT Grand Villa, Theme Park View of course, AKL Grand Villa, Savanna View of course.
Days: 2 wks (1 and 1)
Special Events: V&A Chef’s Table
Location: WDW
Resort(s): Wilderness Lodge theme park view
Number of Days: 10 days
Special Event(s): Christmas without the crowds.
Who would tag along: my immediate family (DH and 3 DS’s)
Location WDW
Resort Cabins at Wilderness Lodge, Bungalows at Polynesian, BLT 3 bedroom villa (is there a 3 bedroom?)
Number of days 14
Special events MVMCP and Festival of the Holidays
Who: DH, DS, DD, DSiL, and DGDs
Other Comments I like @michelle625 's idea to go at the end of October to also catch the Halloween party, but I really like Festival of the Holidays
Location: WDW
Resort(s): Split stay- ending hotel would definitely be the four seasons. The starting hotel is harder…probably AKL CL.
Number of Days: 14
Special Event(s): Halloween and Christmas. Get there just before Halloween and stay until the Christmas party season started.
Who would tag along: Whole family (this is a dream, because my teacher DH would never get that time off!)
Other Comments: Since the trip would be so long, we would have lots of time to enjoy the pools (especially at the FS), resort hop, other attractions, etc.
Things I’d definitely fit in:
Halloween Party
Christmas Party
Topolino’s (for character dining)
DAH!!! Whatever they offer I’d do.
VIP tour
Waterparks
Dinner with just DH
All the fireworks parties
Four Seasons character breakfast
Tons of relaxing without the kids at FS (since they have a kids club)
So, clearly I’ve thought about this one before…
Location: WDW
Resort: AKL Royal Asante suite/Poly Bungalow
Number of days: 14 - 7 nights at each location
Special Events: MVMCP, Moonlight Safari , Dinner with an Imagineer at HBD. Would love to do another fireworks cruise. Did Illuminations and Wishes that way years ago, and I never want to stand in a crowd to watch fireworks again.
Who would tag along: My hubby and our kids. I guess if my older kids had a boyfriend/girlfriend/partner they’d come too.
Other comments: I’d also love to dine at all the locations that I never get to go to bc of my picky family members. Takumi Tei, V&A, Jiko.
Fun!
Location: WDW
Resort(s): Beach Club and Poly
Number of Days: 14 - why not, right? Lots of time to do everything and still take some relax days!
Special Event(s): Tough call. I want to say the Christmas party, but I also want to go Closer to March when it’s more likely to be swimming weather. Maybe a dessert party? Oh, and early morning magicA! TSL AND Fantasyland!
Who would tag along: Just the family - husband and the boys. It would be fun to do a trip with a bigger group but I always like just being on our own the best.
Other Comments: I miss planning a Disney trip!
Adding to Dream!
We’ve been in March a couple times because it fell in line with Mardi Gras. Disney in spring is AMAZING, so beautiful!
Location: WDW and UOR
Resort(s): WL (accept no substitutes)
Number of Days: 5 (4 WDW and 1 UOR); TBH I can only take so long ‘in the bubble’ before the artifice of it gets on my nerves
Special Event(s): V&A Chef’s Table; MVMCP
Who would tag along: DW, DD
Other Comments: Early December the way it used to be - low crowds (CL 2 and 3)
Im going very early December this year, hope its low crowds! 
I think that the low crowds (In terms of CLs/wait times) from 5+ years ago are a thing of the past, unfortunately. WDW management have gotten quite ruthless with their capacity management and staffing levels.
Location: WDW
Number of days: 14
Resort: split stay BLT 2 bedroom theme park view, Star Wars Galactic Starcruiser
Special events: HEA dessert party, Keys to the Kingdom tour, the Starcruiser events (whatever they might be), Savi’s, Dine with an Imagineer, Space 220, Hoop de Doo
Who would tag along: DH, DS16, DD13
That was fun!
Location: Tokyo Disneyland / DisneySea
Resort(s): What’s the nicest one?! That one!
Number of Days: 3 at parks, 4 in Tokyo
Special Event(s): I have no idea but all of them
Who would tag along: DW
Other Comments: We’re having our dream trip to WDW next year so I went even bigger here!
Location: WDW
Resort(s): Boardwalk, Grand Villa or two
Number of Days: 12 - 14, late January early February is good
Special Event(s): maybe none, tbd
Who would tag along: extended family, Sept 2019 we had 19, but with money being no object fairly sure we could add nearly another 19; might need 3 grand villas if Boardwalk has 'em
Other Comments: table service. At least brunch and supper every day. Parks, resorts, Disney Springs . . .