''R'':
I realize mine is a minority report of sorts, but after just transiting the entire Eastern Caribbean, I have to admit one of the areas we found the least satisfying were the BVI''s. Great clear & warm waters plus good (or better...) sailing breezes, to be sure, but you can find these in many, many other areas of the Caribbean. I found a small ''critical mass'' of culture & interesting island heritage (compared e.g. to the French West Indies islands, or Trinidad), huge mooring fields check-to-jowl with boats (most of them charters - no offense intended) while anchorages were more difficult to find & remote anchorages especially difficult (but possible) to put the boat into. The people were great, but then they are almost everywhere.
Were I you, I''d consider chartering out of Martinque or Grenada or Bequia, provided I was allowed to sail up/down the island chain some distance. This will give you protected waters (in the lee of the N-S
line of islands), vigorous but short ocean passages between islands, an intersting blend of French/formerly British island cultures, each unique in their own right, and a huge selection of interesting spots to visit ashore. Get a small scale chart of the E Caribbean and then plot the charter company locations. Le Marin on Martinque, the S end of Grenada and perhaps Bequia (in the middle of the St. Vincent & the Grenadines - SVG) would be my choices. But in return for this advice, you owe me a toast aboard the boat, preferably with a wonderfully tasty yet inexpensive French wine.
You are correct in wondering about the Christmas Trades, as they''re known. Prevaling winds that time of year are 15-30, tending ENE to ESE, but more the former. Just accept that the main will live with one reef; the
furling jib should be a 110-120, which will be plenty & possibly even furled a bit. Enjoy!
Jack
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