soft sided cooler?

You can but it is much easier to just ask for free cups of ice water at the walk up food stations. If you don't like the taste of Florida water use Propel packets
 
You can also bring your own food in that cooler. We pack our lunch and get the free ice water.
 
Coolers, food are all ok most of the time I go I bring all my food and snacks with me
 

Just ask for free ice and water at ANY I mean Any counter service. Bringing in the bag like that other than for baby formula is only a waste of space and weight.
Plus it will be molested and poked at at every security line, can't wait for the days I don't have to bring a stroller through security
 



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