My wife and I used to do that regularly with friends, in between cruise ship cruising, when we found by cruising an area we wanted to spend more time in.
Offhand I can remember some of the boats we chartered, a C&C 42 sail-an Oday 37 sail, a 42' Trawler Yacht, a CSY44 sail.
IN those days the Morgan 41 and the Gulfstar 50 were the most popular sailboats to charter in the Caribbean.
We cruised the British and American Virgin Islands and the Grenadines.
Those were the days my friend , we thought they would never end.-Tom
We did the BVI again in July of 2020, only this time we chartered a Mooring 4000-3 Catamaran. Our first Cat. Amazing boat! If the BVI ever opens up again our next and probably every other will be on a Cat. Fast, roomy, stable, well equipped. Just too much fun.