Re: Bvi - usvi- svi
To Minnewaska's question: We've chartered out of the BVI a couple of times, but never left the BVI then, and don't know about the check out/check in procedure when you go to the USVI. We've done the USVI-BVI split at least 4 times, but always out of Red Hook. You might consider this for the convenience of flying in to STT and skipping either the ferry or a puddle jumper to Beef Island from San Juan.
We've always stayed aboard the night before the charter in Red Hook. Island Yachts has had a very reasonable rate for staying aboard the night before the charter. You've got several restaurants within a hundred yards of the charter base and you can self-provision across the street if you wish.
Here's a suggested itinerary for a 3 night/4 night USVI/BVI split:
Day 1 - get off the dock and head to the north shore of St. John (Maho Bay) and start to unwind. Park mooring for the night.
Day 2 - sail around Mary Point to Leinster Bay and pick up another park mooring. Snorkel off the beach or (better) at Waterlemon Cay. Hike to the Annaberg sugar mill. Day 3 - Sail to Jost van Dyke and check in/out of the BVI, allowing for 4 days in the BVI (fees based on your stay). There are moorings in Great Harbour now. You might check out Sand Castle/Soggy Dollar Bar at White Bay (you might leave your boat in Great Harbour and take a taxi.) You can hang out at the beach and may consider making a reservation for the 4-course dinner at Sand Castle (not cheap, but worth it.) It's casual, but beachware is not appropriate. You have the very casual Foxy's in Great Harbour, if that's your choice. An alternative is Little Bay where you can pick up a mooring and take your pick of restaurants. You'll definitely have a quieter night here.
Day 4 allows you several options: check out picture-perfect Green and Sandy Cays before the upwind slog along the north side of Tortola. A snorkel stop at Monkey Point, Guana Island, is nice. From there you'll motor to Marina Cay and hope for a mooring. Pussers restaurant is OK and you can replenish your water the next day at the dock or wait til you get to Spanish Town.
Day 5 - head to Virgin Gorda. You can try your luck with the day moorings at the Baths, but we prefer to take a slip at the Virgin Gorda Yacht Harbour in Spanish Town. You can pick provisions there, get a hot shower, top off your water tank. You can take a taxi to the Baths, which is more relaxing than approaching from the water side. Bring your snorkel, towels, camera etc., in a backpack. The Top of the Baths is another restaurant we'd recommend: $$, but worth it.
Day 6 - Leisurely sail down the Drake Channel,with optional stops at HMS Rhone, Deadmans Bay (lunch on the hook or ashore) and eventually pick up a mooring in the Bight, Norman Island. Snorkel off the boat (if your mooring is close to shore) or the Caves, where you might arrive by dinghy. Dinner at Pirates; suggest reservations if you have a time in mind. You can also hike on the island, but suggest sandals rather than flip flops.
Day 7 - sail to Caneel Bay/Lind Point to pick up a mooring for your dinghy ride into Cruz Bay, where you'll check back into the US. Bring the whole crew--at least it's fast and free. You can check out the shops and restaurants (bring a flashlight for the trip back to your boat if you are staying for dinner. Hopefully you locked your dinghy!)
Day 8 - Short sail back to Red Hook for your check-in.