We also have a collapsable rolling cooler (like the ones from Costco &
Walmart etc.) but when it came time to pack that puppy had to stay home! Even folded down the bottom end was still like 9" thick and it weighed 5 Lbs!! When you're flying in today's world THAT is huge! If you're driving to the port then it's not a big deal. But if you're flying & trying to get everything into 1 bag per person under 50 Lbs it's really, really hard and something's gotta stay behind! Of course, our vacation was 10 days - if you're ONLY doing a 3 or 4 n cruise then you won't be bringing as much so you would have more flexibility. It depends on your whole trip length how much room / weight you can afford to bring. For me, the rolling cooler would've wasted precious space & weight. We got along fine with our little folding
DCL cooler bag that mashes down into NOTHING to pack and probably only weighs 1/2 Lb. I worked out a deal with our stateroom host where I would just hang the big ziplock bag on the outside of our door handle in the mornings and when he came on duty at 8:00 am he would swing by & grab it & go fill it with ice & bring it back!