The Caribbean offers the most consistent sailing weather on earth: steady trade winds, warm water, and a “Winter” season that coincides with cold Northern winters. For a one-week yacht rental, the British Virgin Islands (BVI) remain the gold standard because the islands are close together, the mooring balls are plentiful, and the beach bars are legendary. Here is a classic 7-day itinerary starting from Tortola.

Day 1: Tortola to Norman Island. After provisioning in Road Town, sail 40 minutes to Norman Island, the alleged inspiration for “Treasure Island.” Snorkel through the “Caves” and then move to “The Bight” for the night. Here, you must visit the Willy T (William Thornton) floating bar. Jump off the top deck into the water—it is a rite of passage.

Day 2: Norman Island to Jost Van Dyke. A short morning sail to Jost Van Dyke. Anchor in Great Harbour and walk to Foxy’s Bar, a world-famous shack where Foxy himself sings live. In the afternoon, move to White Bay (though you must take a mooring ball or taxi over land because the reef blocks boats). Drink a “Painkiller” cocktail at the Soggy Dollar Bar.

Day 3: Jost Van Dyke to Cane Garden Bay (Tortola). Sail back to Tortola’s north shore. Cane Garden Bay is a bustling crescent of beach bars, jet skis, and vibey nightlife. This is your “laundry and shower” day. Eat fresh conch fritters at Myett’s.

Day 4: Cane Garden Bay to Anegada. This is the longest sail (approx. 25 nautical miles) and requires careful navigation because Anegada is a low-lying coral atoll that has wrecked many ships. But the reward is Lobster. Anegada is famous for its giant spiny lobster, grilled fresh at restaurants like Wonky Dog. Rent a jeep to see the flamingos at the salt ponds.

Day 5: Anegada to Virgin Gorda. Sail down to the Baths. This is the most photographed spot in the BVI—giant granite boulders forming sea pools and grottos. Arrive before 10 AM to avoid the cruise ship crowds. Take a mooring ball just off the beach.

Day 6: Virgin Gorda to Cooper Island. Rest day. Sail to Cooper Island, home to a rum distillery and one of the best beachfront hotels. Snorkel the “Shipwreck” near Cistern Point.

Day 7: Return to Tortola. Sail back to Road Town, refuel, and enjoy a final dinner at Pusser’s Landing before flying home.