Ferry Connection Question and Other Options

My apologies if this has been asked recently, but my family and I (me, wife and two children) are planning a land based trip to Virgin Gorda around Christmas. We've done this sort of trip before but the travel logistics are always a little different. The best flight I can find so far has us landing in STT at 2:25 on the 16th of December, and there is a Speedy's Ferry that day that leaves Charlotte Amalie at 4:00. I know it all depends on uncontrollable variables, but is this a "do-able enough" scenario that you would not consider it foolish? By the way flying to VG directly would be our preference, but right now the $$$ seem out of our comfort zone. One other question -- it's possible that some friends of ours (a family of five) may be traveling with us. If that does happen, does it open up some other possibilities like a charter boat ride that might otherwise be too expensive? Thank you for any help.

That SHOULD be plenty of time..if you can do carry on only that would be a big plus..

The ferry schedule may show a departure time of 4PM, but in my experience the actual departure time will be 4:30, 4:45, 5:00 or later. The reason is that VG retailers take the morning Speedy's over to St. Thomas and go shopping for supplies to stock their shelves with, and it can easily take an hour and a half or more to load their boxes of merchandise onto the afternoon ferry to go back to VG. We took Speedy's afternoon ferry from St. Thomas to VG last May and watched as two guys loaded a pile of boxes easily the size of two dumpsters for over an hour before they even started on passengers luggage. It was past 9PM before we cleared C&I on VG, and nearly 10 before we got to the villa. So, an obviously long answer to your question is yes, you will have plenty of time to make the "4 o'clock" ferry, even with checked bags. You will also have time to get a beer and a sandwich at the Petite Pump Room, and strike up a conversation with fellow traveler's and make some new friends. <img src="http://www.traveltalkonline.com/forums/images/graemlins/Groovin.gif" alt="" /> <img src="http://www.traveltalkonline.com/forums/images/graemlins/jester.gif" alt="" />And how come it isn't May yet?