Hi

I'll let others comment on sailing times, but days 3 and 4 are really hard logistically. Drive times from Beef Island to Bomba's and Road Town to West End are each ~45 minutes.

You don't mention your flight time out of STT, but keep in mind that you can catch the ferry in Road Town, and that you need to clear immigration/customs when you arrive back in Charlotte Amalie. For reference, we took the 10:15 ferry out of WE yesterday (10:00 out of RT) and arrived at the airport around noon.