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September, 2025: Halloween on the High Seas!

My first EVER Disney Cruise! My sister and I are doing a short-but-sweet 3-night “Halloween on the High Seas” cruise on the Disney Wish. It literally goes from Florida to Nassau to Castaway Cay and then back to Florida. For obvious reasons, we are referring to this trip as Sisters on the High Seas! Ha. This is like a normal Disney Cruise on steroids, theming-wise.

Until recently, I’d been resistant to the whole idea of the Disney Cruise. I have no idea why. Perhaps I thought the lack of rides would somehow make it less… fun? Or maybe I felt so much attachment to the parks that I felt like a being anywhere else wouldn’t cut it. It’s really all about the theming and the vibes, though, in which case I think I’m about to become hooked on the whole cruise thing (oh god, am I going to have to sail on all the ships now?). From what I can tell, this cruise is basically Mickey’s Not So Scary Halloween Party, but on a (very) large boat, and spread out over several days, which sounds fantastic! I totally get it.

My sister and I live on opposite coasts so we’ll meet up the night before the cruise. It’s a very easy flight for me, but a bit of schlep for her so I appreciate it all the more that she’s doing this with me (even though it was totally her idea! She has the best ideas…). I plan to head out a couple days early for a little park time - and to see if I can get a rez at Geo-82. [update: I have a rez at GEO-82 the day before. But now I have to see about Beak & Barrel…]

I’ll be doing a split stay - first night at The Contemporary, second night at Pop Century - a value resort on the skyliner route! I’ve never stayed at Pop C before so while I’m a little underwhelmed about the room itself, I’m excited to walk around the PopC/Art of Animation area and check out the theming, especially around AoA. I am not going to rush around trying to pack too much into the ~2 days because it’s really all about the cruise. Originally I had two nights at PoPC and then I got the Incredi-Pass and things escalated from there. Night 1, I’ll be watching the Fireworks from the CA Grill terrace and then heading to my room. Next day, I’ll make my way over to EPCOT for my GEO-82 rez, check into Pop-C and end the day back in the Magic Kingdom area for Storybook dining at Artists Point, which is the Snow White themed dinner.

As far as the cruise itself goes, I’m not an “outdoorsy” person, so I’m not signing up for any excursions. I’ll take a walk around the two ports of call, but I would much rather explore the ship and save my energy for the Halloween events in the afternoon and evening. It also seems like a great time to Disney Bound and cosplay and all the rest of it, but I might end up in a tee shirt and jeans the whole time and cosplay as Person Who Couldn’t Be Bothered Once They Got There.

Let’s hope the weather behaves itself. We have insurance.

Aside from just the entire thing, I’m looking forward to:

  • Halloween themed food!

  • Pirate night!

  • Trick or Treating :)

  • Doing some “Color Bounding” - wearing appropriate
    colors and slapping on some ears or a hat!

Update - My ADR window opened and I have a confirmed lunch rez at GEO-82
and a very early dinner (like 4:30!) at Storybook Dining - where I am planning to Disneybound
as Snow White but with a retro vibe.

I also put together my pirate look for Pirate Night and a Jack Skellington-ish look for the Halloween party.

October, 2025: Mickey’s Not So Scary Halloween Party

Ever since I went last year, I’ve wanted to go back - and take the kid! I knew she’d love it. It’s silly and fun and there’s candy and costumes and food and a catchy song. Thanks to my abundant JetBlue air miles and Mosaic 2 status, our flights are costing a whopping $22 total ($11 each) for seats with even more legroom. We’re going to zip down early Saturday morning, stay at the Contemporary so we can be within walking distance of the party on Sunday night, and then zip back on Monday afternoon and be home in time for dinner. Monday is a school holiday that is currently only observed by two states, so the parks won’t be teeming with the usual school holiday crowds - they’ll just be their normal level of average crowdedness. And yeah, it’s hurricane season… but I was there last year during peak hurricane season and it wasn’t too bad so I’ll keep my fingers crossed.

Alright, let’s BOO this! ;)

January, 2026: Solo Trip

Another one week solo trip!

It’s too soon to have any detailed plans, but the gist is to check out Animal Kingdom Lodge for the first time. I also want to go to the new GEO-82 lounge in EPCOT so I’ll need to make a reservation once the 60 day window opens on 11/18/25. One goal I have for this trip is to do as much free stuff as possible - that is, just go around a see things and be in environments and just sit and people watch - and maybe lean more into the fireworks and parades and that side of things.

So far, I have my accommodation and flights booked. The flights are JetBlue (miles - and I used my Mosaic status to get extra legroom so the entire thing was $11) and I’m doing a “split stay”: 4 nights in a preferred view Studio at BLT (Bay Lake Tower), a night at Animal Kingdom Villas (Jambo House) , and then 2 nights at Grand Floridian (aka Grand Flo) in a studio with a view of the park so I can watch the fireworks (my belief is that Grand Flo is what WDW has in lieu of a Disneyland Hotel - I mean, you can’t be calling yourself a ‘World and then have a ‘Land hotel - and since this will be my first time actually staying there, I will have stayed at all of the The Disneyland Hotel hotels).

For park tickets, I priced out 5, 6, 7, and 8 day park hopper tickets and once you get past 5 days the marginal cost of each additional day is very low - the difference between 7 and 8 days is $40 - so I’m planning on getting an 8 day ticket to keep my options very open. I want to build in some resort time and, of course, plenty of quality time just a sittin’ on ye olde monorail… I will not be doing any lightning lane nonsense - not with an 8-day park hopper. That would be ridiculous! update: After doing the math on all three trips, it was cheaper to get the annual Incredi-Pass (at time of writing it came with a $100 GC as well). Not only did I save a little bit on the park tickets themselves, but I re-booked my hotel rooms (for the Fall ‘25 trips) at the Annual Passholer discount rate and saved even more (heh heh heh, “saved”). There are some additional discounts at shops and restaurants but they look to be the same as what I get with my Disney Visa and there’s no stacking. It was definitely worth it based on this year. Next year is going to be a light year in terms of trips. The pass expires September ‘26.

Side note: I booked the January hotels by renting DVC points, which means I paid 54% rack rate but it’s non-refundable. This was well before I got the Annual Pass, so I’m going to check back nearer the time for any lower AP rates on those same rooms just to see what might have been. Having the flexibility to change, cancel, or spread out the payments make it something to consider in the future.

I am counting down the days. At time of writing, the days is… so many days.

Spring Break, 2026 (tentative)

Whelp. It worked! Now that I have the Incredi-Pass, the lure of perceived value is too strong! Well played, Disney. Like Thanos, you are inevitable... I booked 6 nights at the Caribbean Beach Club Resort for the kid and me for her Spring Break. I’ve put down a deposit on the room and am hoping for a passholder discount to kick in nearer the time. I wanted to do some kind of trip for her and thinking about planning something more complicated - and expensive - seemed too daunting. So… here we are. It makes me happy, and she seemed very into it. So why not?

Is it too many trips? Probably. Should we go somewhere else, do literally anything else? Probably. But it was definitely cheaper than doing an all-inclusive resort package at one of those Caribbean places. It’s definitely not cheaper than staying home and not doing anything, of course, but I don’t find that restful. And I think getting away is good if you can swing it. I don’t find “staycations” at all useful. Every weekend I have a staycation right here in New York Ci-Tay where I live and I don’t come out of it feeling any less stressed than when I went in.

I’m very excited to stay at Carribbean Beach Club - a moderate resort. Partly because of the price, but also for the different experience we might have there than our usual “Disney” vibe, which is to be as close to MK as possible and run around like the entire thing is about to close and we’ve got to squeeze in as much as possible before they turns the lights off forever. I like the idea of going more often and… uh, not doing that. Perhaps we’ll spend more time at the resort taking advantage of the little beaches and pools and general “island” theming and actually relax.