I’ve never had to do this and will be facing this situation in late November. We will hopefully not have to check a suitcase (remains to be seen how much DD packs). Do I just go up the the gate counter early to let them know I have a stroller or do I just walk up with one at boarding and they do what they do?
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Most airlines prefer that you approach the gate agent before they start boarding to get a gate-check tag for your stroller. They can usually give you one when you scan your tickets for boarding, but it slows things down.
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If the kid is old enough to walk through the airport (and all mine are now) you can also check the stroller, I believe for free even if you don’t have any other bags, where you would check any luggage. But that’s only if you don’t want to have to navigate a stroller through TSA. Which I already hate doing. So ditching the (in our case double) stroller before that point is a bonus.
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Yes I’ve done this before with a couple different airlines, and when you check in at the kiosk, it usually has a stroller as an option and there is typically no charge.
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He will just be turning 2. Do you think the stroller is less prone to being damaged with being checked with baggage handlers vs gate checked?
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Mom of 5 kids here, youngest is 6 and will be 7 by next trip so we are at the same crossroads. Our youngest several kids are all 4-5 years apart and we used to go every 4 years when the baby was close to 2, so our 6-7 year olds would mostly walk but occasionally double up in the single stroller for a break. I did buy a second, second-hand City Mini for one trip years ago when my youngest were 2 and almost 6 because I knew the 6 year old was not ready for walking it all then. The thing I am dreading about going without a stroller is not having the place to lug and store our stuff. Soft-side cooler full of water bottles, jackets, all the emergency mom-junk I feel I have to bring, etc. It’s like a mobile, free storage locker! I always gate-check it and then pick up at the arriving gate; it becomes a luggage cart to help lug our carryons which is especially nice when I travel alone with kids. I honestly don’t know if I will bring one next time or not, but if I do I think it will be mostly for the stuff-carrying function and less for the kid.
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Not really. They still have to get it to the same place (under the plane) and so mostly the same crew will be handling it and presumably with less time if you gate check it. I just hate hate hate taking the stroller through TSA. We gate checked strollers for flights in 2015 (two umbrella strollers going to Dallas) & 2016 (one double stroller to Orlando) and I hated it, especially the double. TSA is already a cluster & having to deal with the “bomb threat” they consider a double stroller (they had to do some extra security with it that took time & was frustrating) was just more extra than I need in the already stressful airport security scenario.
This year when we went to Orlando was the first time we checked it with bags (and curbside too because it was worth it not having the extra stuff from the get go) and it was blissful. Best airport experience with kids yet. But that was just me personally. Also, the kid has to be big enough to manage the walk through the airport.
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We rented a double stroller and flew with our GB pockit last year. It fits in the overhead compartment.
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With 4 adults, he can be carried, lol. When you check a stroller at the curb would you pick up in baggage claims? I’m assuming when you gate check it’s brought to the gate at landing.
TIA for all the info!
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Mine wont fold THAT small, I don’t think. But now I’ll check. Its a single but I LOVE the mobility of it. Its a 3 wheel and comfy for long sitting.
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Yes and yes you got it all correct!
The adult to child ratio is definitely in your favor!
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Another thing to consider is yourself - kids that age are heavy. You will probably wear yourself out trying to push 2 kids. You’ll be exhausted then they are. They’re probably better off walking than you pushing. We were thinking we don’t think we would have made it in June if we had to push a stroller.
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Less exhausted than if you had to carry them though! 
(Spoken from experience LOL)
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And then I go back to maybe I’ll just rent one in Orlando. I wonder if there are places where you can pick the type of stroller you rent. I’m pretty particular.
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I like what I like in a stroller so that’s why I’ve always just brought my own.
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I think I would be upset if it got damaged. To replace it would be expensive. I was gifted this stroller and wouldn’t spend the $$ to replace it for a 2 yr old. I would look for something else a bit more suitable. Its DGS so it gets regular occasional use.
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A few other points to consider …
(1) Our 8 year old would be ok in the parks without a stroller, but DW and I often like to walk fast between attractions and DD8 would not be able to keep up with us. So you may want to consider how fast you plan to move between attractions and whether your kids could keep up.
(2) Are you walking between Epcot and DHS at any point? That may be a tough walk for the kids without strollers.
(3) If it rains, we find it easier to move around (and/or leave) with the kids in strollers.
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Those are good points, but for me it’s:
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Strollers are great when moving between attractions but overall they take more time in backtracking!
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Definitely a good time for a stroller.
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I find it less stressful without a stroller. Trying to find a stroller parking spot that is covered or not exposed, or worrying about a rain shield, is annoying. If kids are capable of moving on their feet, it ca be easier to duck out of the rain quickly without a stroller. But I agree there are some situations where just hauling out of the park in advance of rain can be a benefit.
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Definitely an option but I feel like the worse walk is to the bus stop at the end of the night.
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My kids are tiny so don’t think pushing a stroller would be an issue. I still wouldn’t want to carry far but I’m thinking I could at the end of night when it’s crazy busy.