As someone who has chartered both ways , out of St Thomas and out of Road Harbour, take which ever is most easily open to your calendar and available for your plane-fare and then make any other operator down range ask for your business if you want to do a similar trip after your first.

Unless, of course, your wallet makes decisions without consulting your Admiral, in which case your charter vacations probably need to be guys-only or ladies only and then you can explain to the Admirals exactly why you feel that way..

Smile. Book a USVI charter. If you've not chartered out of the USVI since 2002, and perhaps never before that, chances are you've been leery of the whole C&I dance, and you've never visited Waterlemon Cay, or either of the Lameshur bays, Christmas Cove or any of the iconic St thomas sail destinations.

Now is a great chance to break out and just do those things. I know you might not miss them if you stayed away, but how honest a traveler could you be if you only flew in and out of St Thomas and never saw anything else than a view from a taxi window ?