I would suggest taking an ASA
or equivalent course and bareboat
charter your own boat. Then invite couples you already know to come and share the expense. Also BVI seems to be better suited for bareboat
chartering than USVI.
I took a week long " Learn n Cruise" from San Juan
sailing in Bellingham WA. We cruised the beautiful San Juan Islands
for a week and learned the ropes earning three ASA
certificates giving us the qualifications to charter and captain
boats throughout the world. It really opens up the options and will give you the confidence to venture out on your own. Then you can invite those you already know and like. And you will probably meet others on the same Trip who have similar desires to cruise
other places. We did BVI, and it was very easy chartering after sailing the San Juan's. Good times, in both places.