Have been to the BVI twice, was thinking it might be fun to
charter in the windward/leeward chain. Any suggestions?

I'd stick with the BVI's. Anyplace else you have to put up with a swarm of
boat boys everytime you drop the hook. It's like having 20 dirtball Boobsprits
clinging to the side of your boat trying to sell you stuff while 20 more are
trying to steal your stuff.
S/V Express 30 "Ringmaster"
"No shirt, no skirt, full service"