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Set sail on the Caribbean Sea and glide through the land of the pirates. Picture remote sandy beaches, lined by swaying palm trees hiding buried treasure and private islands surrounded by glittering waters and incredible wildlife. Whether you are hiking a rainforest, visiting the infamous Treasure Island or relaxing on an inflatable beside the yacht with a rum punch, explore the islands at your own pace, pause for a minute or stop for hours; it's up to you.

Sail and Stay - once you have decided on the sailing part of your holiday, it's time to think about when and where you would like to spend your stay. Hotel stays can be added on before or after your sailing adventure and while there are many options available to you, we would suggest opting for a private island in the British Virgin Islands or taking the short hop over to Antigua.


7 Days

Recommended For

Adventure, Beach, Couples, Cruise, Family, Honeymoons, Luxury Holidays, Sailing, Weddings Abroad, Wildlife


Private basis

a person standing on a beach with a sunset in the background

Trip Highlights

  • Explore the Baths National Park
  • Discover coral reef and wreck dive sites
  • Catch and cook your own dinner off the back of the yacht
  • Experience rainforest hikes
  • Visit Norman Island, inspiration for 'Treasure Island'
  • Relax onboard or find hidden beaches to dip your toes in the sand

Start your Journey

Day 1

Wickhams Cay II to Cooper Island

Sailing time: 1 hour 30 minutes

While you familiarise yourself with your luxury yacht, enjoy a refreshing beverage on the deck as the gentle trade winds cool you. Cruising southeast from Tortola, your sailing adventure starts with a leisurely sail to Cooper Island. In the surrounding waters, anchoring has been prohibited to protect the nests of turtles gliding through the shallows, so you’ll be heading to the sheltered moorings. Rum, rum and more rum Home to the largest collection of rum in the British Virgin Islands, with over 100 varieties from around the world for you to sample, the Cooper Island Beach Club is well worth a pit stop. Don't leave without trying the homemade chocolate mint rum.

Wreck diving

Cooper Island has some of the best wreck sites available, many of which are located in Wreck Alley where a number of vessels have been intentionally sunk and make for wonderful habitats for an array of marine life. In addition to these, there is the RMS Rhone, sunk during a hurricane in 1867;this Royal Mail steam boat is off the coast of neighbouring Salt Island and has been reborn as a home to shoals of groupers and turtles.

Day 2

Cooper Island to Spanish Town

From Cooper Island, you'll set course north passing Ginger and Fallen Jerusalem Island, before following the Virgin Gorda coastline toward the lively and bustling Spanish Town. From here, you can pick up a rental car or taxi and venture to the Gorda Peak where you'll be rewarded with spectacular ocean views. Come the evening, relax in a waterside bar and watch the sun set over the Caribbean Sea. The Baths Years of volcanic eruptions and crashing salt waves have formed Virgin Gorda’s National Park. The granite landscape is awash with grottoes, caves and natural arches all begging to be explored. Don’t forget your camera when you head ashore;this is a photo opportunity not to be missed.

The Dog Islands

Great Dog, George Dog and West Dog of the coast of Virgin Gorda are a great stopping place for lunch. Ask your hostess to pack you a picnic and find a secluded sandy bay to be dropped off at. Work off your lunch by exploring the cliffs and caves around the islands before being collected by your skipper to carry on your adventure.

Day 3

Spanish Town to Marina Cay

Sailing time: 2 hours 30 minutes

Embark on an open water sail across the Caribbean Sea to the tip of Tortola and Marina Cay. This tiny emerald islet is surrounded by coral and is a prime snorkelling spot. Workup an appetite in the shimmering waters before pausing for lunch; make use of the deck and enjoy a freshly prepared meal with a view, washed down with a chilled drink. For the afternoon, the choice is yours: explore the small cay, head to the neighbouring Scrub Island, great for divers, or simply enjoy the vista from the fly bridge.

Trellis Bay

Indulge your inner culture vulture and visit the local arts centre on Beef Island. Aragorn’s Studio has the best in art, craft, poetry and pottery from the around the British Virgin Islands. The local community also plays host to the popular Fire Ball Full Moon Party, a must do while you are in the British Virgin Islands.

Day 4

Marina Cay to Cane Garden Bay

Sailing time: 2 hours

Venturing along the north coast of Tortola, you'll now be navigating your way between the Camanoe Islands and Guana Island with the mountainous landscape as a stunning backdrop. Entering Cane Garden Bay, you will notice the pristine white sand beach, home to some of the best bars in the British Virgin Islands and the green hills of Tortola beyond, teeming with tropical wildlife. While here, take the opportunity to try out the on-board watersports and skim across the clear ocean, or don your walking boots and hike the island’s rainforest.

Callwood Rum Distillery

Rewind the clock and learn about the history of rum and how it is made. With both white and gold varieties available for sampling, you'll be able to pick a new tipple and stock up for when you get home.

Guana Island

While passing this picturesque island, why not take the opportunity and add an extra stop to your journey? White Bay is ideal for mooring and once ashore there is plenty for you to see; be sure to pack a camera as the island has rare wildlife species that are not to be missed such as the vibrant Caribbean flamingo, red-legged tortoise and stout iguana.

Day 5

Cane Garden Bay to Great Harbour

Sailing time: 1 hour 30 minutes

Today, you'll head westbound toward Jost Van Dyke; on route, you will pass Sandy Cay;this aptly named islet is little more than a sand bank at sea and great for a castaway themed lunch spot. When you are ready, hoist anchor and continue until you reach the southern coast and the calm waters of Great Harbour, where you can enjoy a candle lit dinner on board, surrounded by twinkling waters. Further afield, you'll find White Bay that's home to a host of bars and is the ideal place to listen to live music and dance the night away Caribbean-style while working your way through the cocktail menu.

Lost in time

Jost Van Dyke is exactly that;lost in time. The undeveloped beach doubles up as the main road and the shores are scattered with shack bars. There is a distinct lack of distractions, with no TVs or computers and only 150 full time residents’ so the emphasis is on socialising with the friendly locals.

Soggy Dollar Bar

Named after the soggy notes that sailors once handed to the barman after swimming ashore, a tradition that is still observed by many, this shack in White Bay is home to the infamous ‘Painkiller’ cocktail; a heavenly mix of tropical fruit juice, coconut and nutmeg with a healthy dose of rum. This intoxicating frozen brew is high on the British Virgin Islands bucket list; follow tradition and swim a shore but be sure to get your skipper to collect you.

Day 6

Great Harbour to The Bight

Sailing time: 2 hours 30 minutes

Picking your way through the Thatch Islands before skirting the edge of the US Virgin Islands, you'll next sail south to Norman Island. Said to be the inspiration of ‘Treasure Island’ and surrounded by coves and bays, it's not hard to see how. Once frequented by pirates looking to bury their loot, Norman Island is now uninhabited with the exception of a few wild goats. Dotted around the edges are many caves, great for snorkelling, and if you venture far enough into the cliffs divers can enjoy the unique opportunity to experience a daytime night dive.

Willy T’s

Visit the island’s schooner, ‘William Thornton';a floating bar and restaurant that operates from the harbour and hosts one of the top nautical parties nights in the British Virgin Islands.

Pirates Bight

Live bands perform here every week in the chilled harbourside bar. Look out over the moonlit waters with a Bushwhacker or Rum Bucket cocktail and play your next day’s adventure.

Day 7

The Bight to Wickhams Cay II

Sailing time: 2 hours

Your final day of sailing takes you north, past the Peter Island. Privately owned and perfectly formed, it is the perfect place for a stop with numerous beaches to choose from; why not stop for a snorkel or else head to Deadman’s Beach Grill for a local speciality lunch? In the afternoon, continue on to Wickhams Cay II and the capital of the British Virgin Islands, Road Town.

Road Town

In contrast to the smaller islands, this horseshoe shaped town is the hub of the country with bustling shops and an international community. Spend a few hours wandering around the markets, selecting holiday trinkets before moving on to the next leg of your adventure.


  • Fully-qualified, English speaking skipper
  • Yacht Damage Waiver

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