Itinerary: A Virgin Islands Ten-Day Sailing Adventure

Renting your own sailboat, with or without a skipper, is the ultimate Virgin Islands vacation. You choose your own schedule, unfettered by ferry timetables. Quiet coves and empty beaches are yours. And the view from your deck is different each morning. Trade winds, mild weather, and generally calm conditions make the Virgin Islands favorable for sailing, and the British Virgin Islands are the epicenter of the charter yacht industry.

Day 1

Fly to Terrance B. Lettsome International Airport, Beef Island. Check in with your charter boat company, provision your yacht, and receive your safety briefing.

Day 2

Sail to Jost Van Dyke with a pit stop for snorkeling at Sandy Spit. Head to Foxy’s Taboo for lunch, and then hike to the Bubbly Pool. In the afternoon, sail around to White Bay for a Painkiller. Drop anchor in calm Little Harbour and eat fresh fish and lobster at Sidney’s Peace and Love for dinner.

A sailboat heads into the sunset in the British Virgin Islands.
The British Virgin Islands are the sailing capital of the Caribbean. Photo © Deanna Keahey, licensed Creative Commons Attribution No-Derivatives.

Day 3

Spend the morning sailing from Jost to Norman Island. Let everyone take a turn at the helm. After lunch at the Willy T, dinghy over to The Caves to snorkel with darkness-dwelling sea creatures. Come ashore for an upscale dinner at Pirate’s Bight.

Day 4

Rendezvous with a dive operator, and snorkel or dive the RMS Rhone. In the afternoon, sail to Cooper Island and pick up a mooring. Tune up your taste buds at the rum bar, and have dinner at Cooper Island Beach Club.

Day 5

Kayak from Cooper Island to Salt Island and spend the morning hiking, photographing the salt ponds, and exploring the old settlement. In the afternoon set sail for Spanish Town, Virgin Gorda. Pick up a mooring and dine at CocoMaya.

Virgin Islands travel maps by region
Virgin Islands travel maps by region

Day 6

Spend the morning exploring The Baths National Park. Swim ashore and hike the trail to Devil’s Bay. Snorkel around the giant boulders. In the afternoon set sail for Anegada and pick up a mooring at Setting Point. Eat a lobster dinner under the stars at the Anegada Reef Hotel.

Day 7

Hire a taxi out to Keel Point and learn how to stand-up paddleboard. In the afternoon drive to Loblolly Bay to snorkel on the horseshoe reef. Eat fresh-caught swordfish at Neptune’s Treasure for dinner.

Day 8

Sail to Trellis Bay, Beef Island. Pick up a mooring and dinghy ashore to browse the local art and pick up gifts at Aragorn’s Studio. Snorkel the reef at Marina Cay and have dinner at The Island Last Resort.

Day 9

Sail to Cane Garden Bay and drop anchor. Boogie board on the waves and explore history at Callwood Rum Distillery. Take a taxi to Bananakeet Café for the sunset and dinner, and then dance the night away under the stars at Quito’s Gazebo.

Day 10

Return your boat and head to Beef Island for your flight home.

Related Travel Guide