I was in St Thomas in May and a large group of Jet Skiers rode in from Puerto Rico. It is an annual thing for these guys. they run up and down the Caribbean Many of the jet skis were equipped with extra gas tanks and extra storage capacities with other supplies. They also did this in calm waters. I imagine it could be done with a large group like this but the weather timing would have to be right and you would have to have extra gas. Preferable with a large group so you are not stranded alone.
Gasoline is lighter than water, so you could have float tanks that you tow behind for refueling.