[camaraderie]

I second the notion of checking out the caribbean1500 rally which leaves from Norfolk to BVI''s in early November each year. The offshore route will get you down there in about 2 weeks rather than the months it would take via the ICW and Bahamas and "thorny" path.
The normal route is head east till you hit 60 dgrees longitude then right along 60 to Virgin Gorda...subject to weather of course.You can also pick up crew for the offshore passage through the rally. Suggest coming down to the Chesapeake offshore as well so you can shake down your boat and discover any needed repairs and get them fixed before you really head "out there".

On the other hand, it sounds as if you are fairly new at this and this is quite a trip. You can have an equally great time just working your way along the ICW and taking in the sights and crossing over to the Bahamas in late fall/early winter where you will have a great time in protected waters and enjoy some great cruising company as well.

Best...BigGb