Given the size of your party, I can see the attraction, as cwoody said. On the other hand, with that many people, it may be cost effective to do Dolphin Water taxi for the group and have them take you straight to your boat on Tortola. I haven't done a USVI charter myself, but have read and heard really good feedback. As I mentioned, I still think it only makes sense if you are going to spend at least a day or so in the USVI on either end and are doing a charter on the longer side. Captain Jay is a frequent poster on here and heads Waypoints Charters and may be helpful for you to reach out to him for details.

Given the size of your party, have you considered doing two boats instead of one, which would open you up to more options?