The BVI is one of the world's great sailing destinations because it's genuinely easy to sail — protected waters, reliable trades, and destinations close enough that you're never more than a few hours from the next anchorage. Here's a week that hits the highlights without rushing.
Day 1: Tortola → Jost Van Dyke Depart Road Town marina after provisioning. Head northwest to Jost Van Dyke — about a 2-hour sail with good wind. Anchor in Great Harbour or White Bay. Afternoon: the Soggy Dollar Bar. This is not optional. Sundowners on the boat. Sleep in the bay.
Day 2: Jost Van Dyke → Cane Garden Bay (Tortola) Morning swim. If you're up early enough, dinghy to Ivan's Stress Free Bar for breakfast. Head back east toward Cane Garden Bay — a beautiful sweeping anchorage on the north side of Tortola. Afternoon: the beach and Rhymer's Bar.
Day 3: Cane Garden Bay → The Bight (Norman Island) Longer day of sailing — head south around Tortola and east to Norman Island. The caves at the Bight are unmissable: anchor, take the dinghy in, and snorkel the caves. Pirate's Bight restaurant for dinner is excellent.
Day 4: Norman Island → The Baths (Virgin Gorda) Sail northeast to Virgin Gorda. The Baths are the BVI's most famous landmark for good reason. Get there early — before 9am if possible. After the Baths: lunch at the Top of the Bight restaurant. Overnight at North Sound or in the Sound itself.
Day 5: Virgin Gorda North Sound → Anegada This is the blue-water day — a 14-mile open-water crossing to Anegada. Anegada is completely flat (the name means "drowned island") and surrounded by a massive reef. The lobster here is the best you'll eat anywhere. Seriously.
Day 6: Anegada → Cooper Island Reluctant departure from Anegada. Sail back southwest toward Cooper Island — stop at the Dogs for snorkeling en route. Cooper Island Beach Club is one of the best anchorages in the BVI for food and vibe.
Day 7: Cooper Island → Tortola Slow morning. Last swim. Sail back to Road Town. Return boat by 5pm.
This is the itinerary we do for most first-time BVI guests. Every stop earns its place.