My kids and I almost always bring coolers with us to our local zoo, museums, parks, etc. but we’ve never brought one into WDW. For those who do, how cumbersome is it to carry around? What type of cooler/bag have you found works best? Is it ok to leave them inside a parked stroller or is it better to just always carry with you?
If you have one that will fit in your stroller, I would definitely do that! I think any cooler would be cumbersome to carry around, but if you have a small cooler bag that you are leaving it should be fine. You can definitely leave it in a parked stroller. I just wouldn’t leave anything of a large value (camera, phone, lovey, etc) in the stroller.
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If you have a stroller, I loved the cooler bag. Ours fit nicely into the bottom storage bin. We loaded it up with drinks. If you have to carry it, I preferred to start the day with a nice insulated water bottle for each of us in a bag with ice and refill it as needed.
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We love our cooler bag at WDW. We use two giant stroller clips to hang the bag off the back of the stroller, as close to the seat as possible so it doesn’t tip. If you have a freezer, freeze a few water bottles to serve as ice. They will melt and become cold water for you later in the day.
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I used a cooler backpack. Not as nice as not carrying a bag, but good to have an easy carry option for cold drinks. I left it on the stroller sometimes and also took it on rides.
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Just remember that any ice needs to be in a clear zip-lock bag, so that security can see through it. I believe gallon bags are fine to use.
Any loose ice will have to be emptied out before you get through security.
Great idea! I have had many a stroller fall over on me with my big old cooler! I have a couple of huge carabiners that I think will work for clipping. Now off to shop for a decent size cooler that will pack in my already full suitcase. 
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Thanks for that reminder! We’re staying DVC this time so I should be able to freeze water bottles or something to pack in the mornings before we leave for the parks.
Rent a locker? Depending on when you are going, I would not want to be carrying anything around that wasn’t necessary due to the extra body heat. If you have a stroller and can stuff it underneath, that would be ideal. But we’re out of the stroller stage.