Winter Break. Part I - Days 1 and 2: The Longest Vacation Ever... Begins.
Here we go: Winter Break 2026. And of course, as always, I have to start with the pre-show.
The week before the trip, Hallie came down with a very bad cold, which turned out to be RSV. She stayed home from school for two and a half days, and I was a nervous wreck—mostly worrying about whether Madeleine would get it too. But by Shabbos, Hallie was doing much better. Nobody else had gotten sick, and I thought, okay, great—this was our illness. We survived it. Now we can get ready for vacation and everything will be fine.
How wrong I was.
On Shabbos, we went to shul, and there was a large kiddush for a bar mitzvah. I actually met someone there who was going to be on the same cruise as us, and we joked that this could be a super-spreader event. Sunday was totally normal, but by Sunday night, Tzvi was nauseous and up all night, and by Monday morning, let’s just say things were not looking pretty out of either end.
It became pretty clear that some sort of stomach bug was making its way through everyone who had been at that kiddush. We don’t know exactly what it was, but it was bad. Really bad. You can only imagine how I was feeling. There was the obvious panic: who else was going to get it? What if Tzvi was just going to be vomiting and having diarrhea forever? It was really, really awful. But by some miracle, nobody else got sick, and by Wednesday, Tzvi was feeling pretty decent, and off we were.
Our flight was at 5:30PM, so I picked up the kids early from school and we headed to the airport. Check-in was super easy, and the airport was practically empty. I’m telling you—Wednesday at 5:30 is the perfect time to fly. Our flight even pushed back a minute early, we were in the air 11 minutes later, and while the flight was pretty bumpy, overall it was very good.
We landed at Orlando Airport, our luggage came out first, and our transportation was right by baggage claim waiting for us. The ride to Disney was a quick half hour, and we pulled up to Disney’s Bay Lake Tower, a Disney Vacation Club property at the Contemporary Resort.
For this trip, we opted to “buy” DVC points from a woman who sells them, which allowed us to stay in a two-bedroom villa at the Contemporary. Thanks Jay from Toddys for the connection – the best bagels and best Disney tips. We had never done Disney this way before and didn’t know what to expect, but it ended up being really fantastic. It was kind of like blending our stays at Vistana (my parents’ time share) with a Deluxe Disney resort. We got a two bedroom, three bathroom suite with a living room, kitchen and dining table, and laundry! The room was really nice and very spacious. We booked a lake view because a park view is outrageously expensive, except we ended up with a corner room – or as close to a corner as you can get in a round building. When we opened the terrace doors we looked straight out at the lake, but when we turned our heads to the left we had a full view of Magic Kingdom. You can see the castle, Space Mountain, Tron. You can even hear the people screaming on Tron. It’s really, really cool.
We got settled in quickly, unpacked a bit, and then of course the kids were hungry even thought it was 10PM. So Tzvi and I walked to the main Contemporary lobby – it’s a one minute walk across a bridge – where there was a quick service restaurant open.
We ordered pizzas and fries for the kids and then sat down to wait for our food. And then we waited, and waited, and waited. Eventually Tzvi went over to see what was going on and it turned out they had “lost” the ticket. I’m not really sure how that happens, but they were very apologetic and gave us the meals for free.
The kids enjoyed the pizza, and finally it was time for bed. Overall, despite everything, it was a great travel day and start to the trip.
Day 2 – Thursday: Hollywood Studios
Thursday morning, we woke up, got ready, and left the hotel in an Uber to head over to Disney’s Riviera Resort.
It’s a resort that’s only a few years old, but we’d never been there. On the top floor is a restaurant called Topolino’s Terrace, which has a character breakfast featuring Minnie, Mickey, Donald, and Daisy. We’d never done it, so I thought this was a good time to try it. Our reservation was at 10:00 a.m., which made for a nice, slow start to the day. It’s an à la carte meal: they bring out a basket of pastries with jam, Nutella, and butter, and then you can choose an entrée. We were nervous about it not being a buffet, but this was actually way more food than anyone needs. Also, we are on the Disney Dining Plan because we were able to get both kids free. With the dining plan, you’re even entitled to an extra drink with each meal (even at breakfast), so technically we could have ordered breakfast cocktails, but nobody needed that, so we got lattes instead. The character interactions were also really sweet. Daisy even sat down and started fake-playing Old Maid with Madeleine, which was adorable. Overall, it was just a very nice breakfast and one I would highly recommend.
From there, we took the Skyliner—Disney’s aerial gondola system—over to Hollywood Studios. I had never been on the Skyliner before, and it was really cool, by which I mean it was cold and there was no heat. I guess it was better than the opposite – I can imagine it’s awful in those things in August. I should mention Florida is going through a cold spell – the high for the day was 62, but it was just dreary and the real feel was definitely lower. We spent the day walking around shivering in our coats.
We decided we would do Hollywood Studios and Magic Kingdom for this trip because last year we did EPCOT and Magic Kingdom, and we wanted a change. We had the Premier Pass, which meant we could go on basically all the rides whenever we wanted without booking specific Lightning Lane times, which was fantastic.
We started in Toy Story Land and did Midway Mania, Slinky Dog Dash, and the Alien ride. Madeleine was scared of Slinky Dog and did not love it, but overall we had a good time. There was an area where they were displaying three outfits from The Era’s Tour, so that was very cool to see. From there, we made our way to Tower of Terror and Rock ’n’ Roller Coaster. We did a rider switch for Tower of Terror—Hallie did it and loved it. Rock ’n’ Roller Coaster was just me, Hallie, and Shir. It’s funny because they’re in the process of switching Rock ’n’ Roller Coaster over from Aerosmith to the Muppets. It hasn’t closed yet, but all the Aerosmith branding and the pre-show are gone, and they even changed the songs. They’re still Aerosmith songs, just not the ones they used to use. We’ll see how that ride ends up changing.
For lunch, the kids had pizza, and we had Asian noodles in a waffle bowl, which was… interesting. After that, we walked over to Star Wars land. Madeleine didn’t do Rise of the Resistance, but she did do Millennium Falcon. I think she was scared, but she handled it like a champ. We also saw a couple of shows – the Disney Villains show, which was cute, and the Little Mermaid show. Unfortunately, we didn’t make it to the Frozen show—there just wasn’t enough time.
For dinner, we went to Woody’s Rodeo Roundup, which we’ve eaten at several years ago and love. They do a really great vegetarian spread. I honestly don’t remember everything we ate, but it was all BBQ and a lot of food. There’s so much sauce you can barely tell its vegetarian. It was great. The kids also love that every 20 minutes or so, a toy comes on the loudspeaker and announces that Andy is coming, at which point all of the servers freeze until they say the coast is clear. It’s a very cute thing.
After dinner, we debated staying for Fantasmic at 9:30, but it was just too cold. By the time we got out of dinner it was around 34 degrees. We were barely able to walk the length of the main street to get out of the park, so there was really no way we were standing outside to watch a fireworks show.
We grabbed an Uber back to the hotel. Our driver was from Venezuela, and when we asked him how he felt about things, he said, “I am happy Maduro is in Brooklyn.”. When we got back to the hotel we were actually able to catch some of the Magic Kingdom fireworks from our balcony, so that was nice.
All in all, it was a good day.