We did it just after Thanksgivings in 2012. We stayed in the SVI the whole time, but had a good time. Some points:
-- Everything to the east is uphill most of the time. (Keep that in mind if you really go all the way to JVD). But it's downhill on the way back. Van Sant's "Thornless Path" book has some good route pointers to cut down on the upwind slogs.
-- At least in 2012, there were no places to dock a sailboat of any size in the SVIs, short of going back to Fajardo. That means if you need to refill water, you get to schlep it in jerry cans. That can get old pretty fast. A watermaker would be nice.
-- The nicest beach on Culebra (Playa Flamenco) is not the best place for a cruising sailboat. But there's a footpath to it over the hill from the small beach on the northern west coast. (I don't recall the name off hand.)
-- In 2012, several of the restaurants on Culebra were closed. It looked like they were getting ready to reopen. Hopefully they did. The week after thanksgiving, Culebra had pretty much rolled up the streets.
-- We really enjoyed Vieques. If you are there during a new moon, do not fail to take a bioluminescent bay tour. Esperanza has some nice restaurants and bars, but not the best anchorage. Sun bay, just to the east, is a good anchorage, but access back to Esperanza could be better. (You can dinghy out out between bays, but it can get a bit rough).
-- If you are chartering, SailCaribe in Marina Puerto Del Rey is one of the best charter companies out there.