There is not too much to add to what others have already said, but here is my experience:
- was there two times chartering with Sunsail and Moorings (same base). I think Anegada is generally out of bounds, primarily due to the tricky approach for most of the inexperienced charterers but I assume exceptions can be made.
- We did JVD to Anegada and it was a great sail on a single tack
- In my opinion Loblolly Bay itself is worth the trip but also it is the longest stretch of open sea sail, so there is some navigation challenge (in particular the flat profile of Anegada which is almost invisible from a distance)
- we stayed the first night on board and were out on the sea before noon the next day. Also it is advisable to arrange for the provisions delivery in advance so you get it the night before.
- if you try to go from Norman Island to JVD you should be careful to stay within BVI waters as I heard some boats got the attention of the USVI coast guard.
- The itineraries are many and very flexible, the only thing I would suggest is to stay the last night somewhere close to Road Town (Cooper or Peter Islands) so you have a predictable trip to the base as you have to return the boat by 11am the next morning.
Enjoy the sail!