But not the sort of breezy airport traveling that I’d enjoyed in my pre-kid years.

Yeah, I think those days are a long way off still...
I could NOT figure out the seatbelt (the clip just kept ending up right in the middle of the seat!)
I'm not entirely certain what you're saying here, but if the seatbelt buckle is ending up in the middle of the seat, I heard a tip to ask the flight attendant for a seatbelt extender - I did that one flight where I was having trouble and it really helped (brought the buckle to the side of the seat).
I’m considering buying a lighter-weight seat for our Disney trip (a la @duggette backpack seat), but might just do the heavy lifting again and save some money. Anyone have any other recommendations?
Honestly, it depends on what you are willing to have for a travel carseat and how much that is worth to you. For me, I got our travel seat for about $30 and have used it on lots of trips, so it's a no-brainer. And it's like 9 pounds. And I have gate-checked it on flights where we couldn't get a seat for Izzy and I just used one of those cheap orange gate-check bags you can get at the baby stores. No damage, but even if it was beat up, I'm only out $30. I also like that we can leave our "good" seats in our own cars and not worry about them getting beat up on a trip.
I didn’t plan to bring it on the cruise ship… but maybe I should? We aren’t planning to do much in Nassau and will be covered at
Castaway Cay. Thoughts?
I doubt you'll need it. We brought ours on only because we didn't keep the rental car while we were on the cruise (did two one-way rentals), so it was just tucked away in the stateroom the whole time.
But what is one more piece of luggage to pull of the baggage claim and throw on a cart?
Depends how big your rental car is - all that baby stuff (stroller, pack 'n' play, luggage, etc.) can really take up a lot of space.
I’m going to be very cognizant of naps and careful to ensure she gets enough sleep.
I agree that is a smart top priority!
During a recent hotel stay, I put her PnP in the corner of the room, wrapped the rooms drapes around her PnP (and a sofa chair, so that she couldn’t pull on it), stuck her sound machine on the floor inside the drapes, and she slept really well.
This reminds me of the staterooms on the cruise ships. You have that curtain between the bed and the rest of the room. We just had Izzy in a pack 'n' play over near the verandah (with the door safely closed and locked, of course) and we pulled the curtain and let her be in "her room" during naps/night. Worked fine.
Fortunately, she’s starting to take a sippy cup more often. Everything I’ve read has said that kids need to be weaned sometime between 12-18 months. She’ll be 18 months on the trip, and hopefully we’ll make the full transition by then
Hopefully you can transition her for the trip. I think it will be easier. Izzy's first trip was at 14.5 months and she was using sippy cups by then (normal and straws). My favorite travel item for milk are the Thermos Foogo straw cups, since they are easy to drink from, more-or-less spill proof (we've had some issues), and they keep milk cold for like 8 hours. Otherwise, I'd bring a small cooler for your cups/bottles so they don't stink by the end of the day.
I’m not above using the semi-disposable (recyclable!) sippy cups while we go through the parks and just toss (recycle!!) them after a single use.
Yes, we've used the Take 'n' Toss cups before and they work fine for that sort of thing.
Is it easy to find whole milk in the parks? Should I plan to bring a small cooler? How about on the ship? Should I plan to bring a gallon (its just a three night).
It's pretty easy to find whole milk. I'm not sure if a gallon would fit in the fridge on the ship? We ordered room service one night and just asked them to bring several cartons of milk (though we weren't picky about skim vs. whole, etc. at this age - not certain they had whole, but probably). I know that the resort gift shops/dining areas have whole milk in good supply, if needed.
And so… I have not walked with her in the stroller in two months. TWO MONTHS! I AM THE LAZIEST/WORST! So, now she kind of hates her stroller and just wants to walk everywhere anyway.
Ugh, I hope you can get her to accept the stroller again. Work on some bribes, if you need to. Find a local place (a mall or something) that you can drive to and practice with her, maybe?
Has anyone ever traveled with a young child WITHOUT a stroller? How was it? Any fears over stroller theft? Ours is a pretty nice one, but it tends to be covered in graham cracker crumbs and stains. Perhaps a deterrent?
Unless your stroller is VERY coveted, I'm sure you're fine. Lots of people bring expensive strollers to Disney and have no issues. Just know that if it's missing from where you parked it, a CM probably relocated it nearby and you'll find it. We take Izzy some places without a stroller now, but she's almost 3. And, if there's a lot of walking, I'll bring it anyway. It is EXHAUSTING carrying a kid around WDW for days - I know from experience, as she was a stroller-fighter on this last trip.
But Bronner’s (the World’s Largest Christmas Store, also in Frankenmuth), TOTALLY knocked her out. She was just… crazy with overstimulation and it was so fun to see.
So, I guess you'll be hitting up the Christmas stores in MK and Downtown Disney?
Wow, what a bummer about the construction and the point rental company being so stubborn!

That is great about the free tickets and extra FP+, though!
Anyone have any idea if you can use complimentary tickets towards an annual pass?!
Good question. I know you can upgrade a normal 6-day PH after you've used it at least once. However, there might be extra strings with comped tickets. I know I've heard of people with free 1-day tickets being unable to upgrade. Maybe check with Disney in advance and let them know what happened and what you want to do and see if it's possible...maybe they'll give you free APs instead.
