You'll get cleaner air going W and N past Tortola but somewhat less pleasant conditions. Either way, it'll be on the nose. You can tack
offshore and then
head into Virgin Gorda Sound on a fast beam reach (always fun running the slot).
The N side of Tortola's quite nice and unspoiled but
anchorages can be rolly and dangerous. You'll see few boats so be aware of the conditions. It can get lumpy and wet. Going along the S side of Tortola will be smoother but with lighter winds, and longer. There are also a lot more distractions.
My suggestion:
(1) A brisk sail from JVD to either
Anegada or Virgin Gorda Sound. If the weather's fine, drop the hook off Necker Island for a quick look or maybe lunch at Benner's Bay. In VGS, check out the resorts,
head to Spanish Town for dinner, or hang out in the bay. The volleyball nets are always inviting. So's the pool.
Anegada is well worth the sail. The anchorage is small, the
water thin, but the view, taxi rides to the beaches exciting, the snorkeling incredible, and the seafood stellar. It's one of the few places where you get a great view of the BVIs. And the screaming beam reach to VGS will bring smiles to even the hard
core racer. 12 miles of
hull speed, through a narrow slot between 2 very visible
reefs, and into the calm and welcoming bay!
(2) Next day head to the Bath's early for a few hours of exploring, then scoot for Fallen Jerusalem. If the Bath's are "so done" then head for the Dog's or Cockroach Island. Very small anchorage and some great snorkeling. Fallen Jerusalem's got a couple moorings and is a big change from the intensity of the Baths. If you've got lots of energy you could make a dash to
Cooper for the night but moorings go fast there. I've always liked spending the night at Fallen Jerusalem.
(3) The next day I'd do some sailing, stop by Cooper for lunch and the conch fritters, and spend some time at
Salt Island. Go ashore and say hi to the folks that give the island its name. There's the Rhone for snorkeling or the cut between Cooper and
Salt. If the weather's calm and you want to meet other boaters, then the anchorage off Peter Island can be fun.
(4) From there I'd head out to the Indians/Pelican for some snorkeling and lunch, then to the Caves @ Norman for some quality snorkeling/sunbathing time. Drop the hook close (but not too close) to the Willy T, put your party clothes on and "do" the Willy T. I've not been impressed with their
food but they do know how to party.
(5) Time for
shopping so I'd head to Road Town for the day. Lots to see, good eats, and fine
shopping. If Road Town gets old then you could head down the Channel and either turn to port and into the
anchorages on the N side of St. John or around the corner to West End/Sopers Hole.
(6) Decisions, decisions. You could head back to JVD, head to the anchorages and great snorkeling on St. John, or go for a nice long sail. Lunch at one of those small islands off JVD can really bring things together. And the view isn't bad either.
(7) Back to the real world
So, you need crew? Hint. Hint.