Since you are a frequent BVI-er, I won't give you the standard advice about island travel in September/October -- I'm sure you know the drill.

There are really 2 major areas to bareboat charter. The easiest (relatively) and with the most choices for charter companies, boats, amenities, etc. is the Abacos. The Out Islands for beginners, if you will. The entire area is directed towards travel by boat, with dinghy docks everywhere, and beach bars galore. Sunsail and Moorings are your obvious choices (with power and sail boats), but there are smaller outfits as well. Line of sight sailing within the largely protected Sea of Abaco, and an anchor-swallowing sandy bottom in most places (there are moorings available in a few spots). You would fly into Marsh Harbour (MHH), and most of the bases are there. A huge and well-stocked supermarket (Maxwell's) with convenient liquor stores and bakeries (Must. Have. Bahamian. Bread.) for provisioning. Marinas throughout, so you can get water, ice, etc. Clinics available in most of the major settlements (I'd abraded my cornea on an overnight passage, and got a prompt and free consultation at the clinic in Green Turtle Cay).

A little tougher conditions, but more remote and -- in my eyes -- more rewarding, are the Exumas. There are 2 charter companies based in New Providence (NAS) -- Navtours and Dream Yacht Charters -- that you use as a base to cross the Yellow Bank over to the northern Exuma cays and the Exuma Cays Land and Sea Park. I could spend weeks in the Park (and have), BUT, no restaurants, no groceries, no ice, no water, no fuel. Just some moorings and beaches to die for. There is a little bit of civilization north at Highbourne or Norman Cays, or south at Staniel Cay. And you can visit the damn pigs if you want. Or you can charter out of Emerald Bay Marina on Great Exuma, which has a little more "action." Tides and currents can be a major issue here, so you need to be alert.

Here is my trip report from my last Exuma charter: Exuma Charter. Going back next year, with Navtours.