We do the same thing - we have the Coleman with the hard insert and it keeps the ice frozen for quite a long time. The insert comes out and fits perfectly in our checked suitcase, then I fold the soft sided cooler into it for the flight. We just tip the bartenders to fill it in the morning. We stop at MegaMart or Hi-Lo for a case of RS, case of water, Appleton, and Vodka on the way to Negril. Throw a few of those Mio or Crystal Light water flavors in our bag to mix our own drinks. Fresh juice that we buy on the beach is great as a mixer.
Here's the cooler we have: https://www.amazon.com/Coleman-16-Ca.../dp/B006HFBZEC





