We pack everything essential in a carry on - clothes & toiletries. We check our cooler and another bag that has the "nice to have" stuff like snorkel gear, yeti cups, beach towels, etc. If our checked bags don't make it, it's an inconvenience, but doesn't ruin the vacation. We can always get snorkel gear at the charter base and pick up the other things at the store if we really need them.