A bit of basic info to consider
Shipping: I use Sea Star Lines and am hooked up with a shipping broker that has given me the best pricing available. She is currently working out ball park pricing on a variety of boat sizes starting at 32 ft to give you an idea.
I shipped from Port Everglades, FL ( Fort Lauderdale ) and am quite sure that they also have a terminal in Jacksonville. To give you some idea what to expect my 50 ft Nor Tech weighing just over 22,000 lbs on the trailer was about $ 10,500 total, down and back. I am hoping that a 38 ft boat can be shipped for $ 7 or $ 8,000 but will confirm that in a day or so. Pricing is determined by cubic ft so naturally cats will cost more to ship.
On arrival: Your boat will offloaded and stored outside in a fenced, secure shipping terminal with security. I did not lose a thing during the coarse of my trip. They will hold it for a reasonable length of time until you fly in to receive it. I used a recommended towing company to haul me about 2 miles to the launch ramp. He then took the trailer to a secure storage compound where it stayed until my return to St Thomas.
Distances: From Charlotte Amalie the capital of St Thomas and USVI to Saba Rock Resort at the eastern end of the North Sound and BVI it is only 45 miles. All of it protected waters other than some exposure in the gap between islands. Anegada is another 12 miles to the north of the North Sound. From BVI out to St Maarten it is another 88 miles to the east. That is all exposed water and should only be crossed in good conditions. Also to the west of St Thomas there are some really beautiful islands towards Puerto Rico including Culebra that are easily accessed.
Fuel: Good quality and readily available as it is never more than 10 or 15 miles to a marina. Expect to pay a buck or two more than in the US but a tank of gas will take you all thru the Islands and then some. I will need to check on the octane as I was only buying diesel of coarse. When I went down Island some places only had 90 or 91 octane. It depends on where refined.
Boat size: As you saw from Jay and my pictures, you can manage quite well with a moderate size boat. I would recommend not less than 32 ft and of coarse the bigger, the more comfort if that is important. We saw several Top Guns and lots of center consoles.
Island hopping: The Islands of the BVI form a protective ring around the Sir Francis Drake passage. Often the trade winds are blowing, kicking up the seas offshore but it is still very boatable within the island chain. Many of the islands are only a few miles apart and offer protection. There are some really cool and famous restaurants and beach bars on many of the islands: http://www.articlesbase.com/cruising...er-345076.html