Just returned from this trip. Thanks for input from folks on here. The trip was a breeze, never had a single issue with anything. The boat was perfect for the two of us. We did a lot of sailing so sometimes arrived places a little later then recommended, but usually found we could drop the hook for an hour or less and someone would leave a mooring, so we never spent the night that way. The swell was up the first two days so we had to rearrange our schedule a bit, but it was not an issue, we got everywhere so quickly. I think the highlight sailing was the reach from Leverick to Jost Van Dyke - great wind and big, long, rolling swells - much different type of sea than we get on the Great Lakes (and much more comfortable). I can definitely see returning to this cruising ground in the future.
We're taking a 36i with Sunsail in a couple of weeks. Anything you'd recommend bringing that you didn't, or leaving behind if you brought it? This will be our first charter in the BVI's so any advice is welcomed.