We're really noodling on a plan for the winter. Scheduling is probably going to require we book close to departure and have seen threads on LateSail.com. I would be interested to hear more about them or other places you think are good for last minute booking or deals.
We love the BVI and probably default to going back. However, we've been thinking that a USVI trip may be easier and marginally less expensive. We can fly direct to STT and would be more comfortable getting right aboard. We usually grab a hotel before or after a BVI cruise or both, to avoid stress getting to the ferry or connection flying from Tortola.
Another thought about USVI is seeing St. John's, which we've passed often but never landed.
We're also intrigued over sailing to Calebra off Puerto Rico. It doesn't seem far, but I'm not sure about typical passage conditions. Is anyone familiar with this? I wouldn't think we would have to deal with customs going from USVI to Puerto Rico, but island rules can vary. Do charter companies object?
We're sailing out of Tortola (Sunsail) this January - our first all-sailing vacation down there. We thought briefly about Island Charters or CYOA, but decided for our first time to do Sunsail, with their "double reef week" discount.
We've done land based vacations on St. John 2 of the last 4 years, and LOVE the island. For those vacations we stayed at Maho Bay/Harmony Studio eco resort, which has a nice anchorage and very reasonably priced dinner pavilion. It's not at all fancy, but getting a multi-course dinner with salad bar and ice tea for ~$20-24 is almost unheard of in a resort area. Their art/glassblowing demonstrations and lessons are also really cool. The network of interconnecting boardwalks to get around the property is very cool to see. The resort has a very neat, summer-camp like vibe about it, which may or may not be to your liking.
I mention this only because Maho Bay resort has lost its lease for the land it sits on (not for lack of trying by the resort owner) and the land is in the process of being sold, presumably to a more commercially minded resort developer. The eco resort will close May 2013. So if you have any interest in visiting this trendsetting resort, you would want to do it on this trip.