GTMO has fishing boats and dive craft for just those kind of rentals. It is cool beyond belief to motor by the border and hear the Cuban guards exchanging radio traffic about the boat.
You cannot see the Cuban guards, but you can hear them.
When I was in Panama in the late 80s...they’d gone to the confiscation law enforcement crowd around Miami, and found some open-sea fishing vessel and gotten the government to do a transfer. I think the Mwr folks rented it out virtually every weekend.