Yea... several posts here historically on this subject. And it always ends the same way, i.e., it all depends on what you value and what you consider up/down sides.

One of the posts here suggested that the cruising fees for non-BVI boats is going up. This is true but probably meaningless. Run all the numbers and see where you are. If you bring a boat in from USVI you pay some fees. But you don't take a ferry boat each direction. Only you can figure out the total cost for your party but I'm going to guess that any difference - one way or the other - is going to be in the noise. So cost is probably not going to drive the decision. There are a host of other drivers which you will have to weigh such as the time it takes to get to your boat, the boat condition/equipment/age, provisioning, if you value seeing the pretty bays on St. John, (see previous postings on this issue) etc. If you are not sure I would recommend giving it a try. You can then compare it to your Tortola charter experiences and make a real informed decision if you like/dislike the location.

Is it rougher sailing out of CA in the winter? Maybe. There is about an hour+ motoring (we don't bother sail this portion) ride upwind that is exposed to the swells. But these are long period swells mostly on the nose for most of that 1hr+ ride. I have had guests on this ride and while I was concerned about the people that have never been on a boat I have never had an issue.

Good luck and happy sailing!