Typically coming in from the US the flight will arrive in the afternoon. This means a sleep aboard at the marina the first night normally. You can provision yourself at one of the nearby stores or order provisions ahead of time. There are lots of great dining options in Frenchtown for the first night. From there the captain will join the boat as early as 8:00 AM on the first day. You have tons of options with a full day. You can visit St John on your way to the BVI or choose to go directly to the BVI’s. It is about three hours to Jost or West End. That puts you in Jost, Tortola, or Norman Island easily on the first night.
Anegada is allowed both with a captain or with the proper experience for bareboat customers