Sample 7 Day Itinerary

The following sample itinerary follows the general planning tips in this guide. All charter companies are based in Tortola, and checkout is usually at some point later in the morning.

Day 1: Norman Island

Today visit Norman Island, which inspired Robert Louis Stevenson’s “Treasure Island”, for great snorkeling, a large accessible anchorage, and great dining if you wish. Read all about exploring Norman Island here.

Your goal is The Bight, a large anchorage with plenty of mooring balls and a great place to practice mooring if this is your first time. If The Bight is crowded, Plan B is Kelly’s Cove just outside the Bight.

Snorkeling the Caves on Norman Island, the setting of Robert Louis Stevenson’s bookTreasure Island

Day 2: Marina Cay

Today sail with your forefathers up Sir Francis Drake Passage, also known as “The Pirates’ Gangway”. Read all about Marina Cay and Trellis Bay.

You’re heading for Marina Cay, where you’ll find a great restaurant and a Pussers store for great nautical and pirate shopping. Take the dinghy over to roam the beach in nearby Trellis Bay to see the works of local island artisans. Plan B is a mooring in Trellis Bay, a large anchorage next to the tiny airport on Tortola’s east end.

Going ashore for a night of comedy, music, and great food on tiny Marina Cay

Marina Cay has a fantastic restaurant with gorgeous views at night. There’s also a small laundromat next to the dinghy dock making it a convenient mid-charter visit.

Day 3: Virgin Gorda

Get an early start for the 1 hour sail south to the Baths, one of the most picturesque and exotic adventures in all the British Virgin Islands. Pick up a day mooring and take your dinghy to shore where you’ll enjoy snorkeling and climbing through enormous boulders stacked along the shore — boulders the size of houses.

Exploring the incredible shore at the Baths on Virgin Gorda

Enjoy lunch at the Top of the Baths restaurant before sailing northeast to your final destination in North Sound: The Bitter End Yacht Club. As a Plan B, you might head over to Leverick Bay on the other side of North Sound.

Day 4: North Sound

There’s so much to do in North Sound, you can give the sails a rest today. Snorkel Eustatia Sound, where you can see ship’s canons that have grown into the reef. Take windsurfing lessons or sail a hobie cat around North Sound. Hike the island up to Jack & Burns Point, where pirates used to watch for passing treasure galleons to run aground on the low-lying reefs north of the island. There’s so much to do here, your crew will want a full day to explore. End the day at Saba Rock restaurant. Read all about North Sound here.

Although there’s no sailing in today’s itinerary, consider spending the second night on one of Saba Rock’s moorings, because it includes a free fill up of water for the boat.

Immaculate beaches at Bitter End Yacht Club

Spend a day relaxing at Bitter End Yacht Club in Virgin Gorda’s North Sound

Day 5: Tortola’s North Side

Today sail Tortola’s north side, which is a little more open to the Atlantic and will give you a small taste of bluewater sailing.

Your mooring for the night will be picturesque Cane Garden Bay, or as a plan B you can sail around to Sopers Hole.

Enroute to Cane Garden Bay, stop for lunch aboard at Monkey Point. Here the crew will enjoy a great snorkeling location, teeming with fish and sea life. Cane Garden Bay is a great place to swim along the shore, and the evening air is filled with local musicians playing at the many beachside restaurants spread along the shore. Explore Cane Garden Bay here.

Watching the pelicans fish in the sunset at Cane Garden Bay, where Jimmy Buffet got his inspiration for the song “Cheeseburger in Paradise”

Day 5: Jost Van Dyke & Sandy Cay

You’ll want an early start today for the 1 hour sail over to Sandy Cay, an uninhabited, palm-covered stretch of golden sand surrounded by brilliant, clear-blue caribbean water. Spend the better part of the day here, exploring the tree-canopied trails through the heart of the island while viewing all kinds of birds and island wildlife.

Your mooring tonight is Eustatia Sound, or as plan B you may anchor along Little Jost Van Dyke or drop anchor at Sandy Spit.

If it’s not too late, hike the short trail behind Little Foxy’s Taboo cafe to the Bubbly Pool, a natural jetted tub formed in the rocks along the shore. Natural wave action sends bubbles swirling continually through the clear water pool.

Drop anchor and swim to shore on uninhabited, palm-fringed Sandy Cay

Day 6: Peter Island

Today set sail for Peter Island and Dead Man’s Bay. But no don’t be put off by the bay’s name, this has been named one of the top 10 most romantic beaches in the world. The name comes from the beach’s view of an uninhabited island, the legendary place where Blackbeard marooned 15 of his men on Dead Chest Island. Read all about Peter Island here. On the way, stop for lunch in Sopers Hole and enjoy the charming waterfront shops and restaurants along the shore.

Choose tonight between two neighboring anchorages on Peter Island. Anchor off the beach in Dead Man’s Bay, or pick up a mooring in Great Harbor. Read all about Peter Island here.

Day 7: Road Town

Spend the morning exploring the rest of Peter Island, and then take the short sail back to Road Town in the late afternoon. Your charter company will likely put you back in a slip for the last night which will be very convenient for exploring all the shops and restaurants in Road Town. A favorite restaurant here is the Fort Burt Hotel, which has breathtaking views of Road Town harbor after sunset.