Explore the Caribbean and sail the BVI (British Virgin Islands)!  Sailing the Virgin Islands is an wonderful way to see the Caribbean due to the close proximity of the islands, their stunning beauty, the local hospitality, cuisine, perfect weather and stunning marine life.


When you sail the British Virgin Islands, you get to see everything including pristine white sandy beaches, coral reefs, secret caves, breathtaking sunrises/sunsets, perfect aqua water, secret pirate caves and of course pirate treasure, maybe.


We island hop around the British Virgin Islands each day, stopping for a swim stop where you can look for sunken ships, sunken planes and explore pirate caves.  We stop for the evening in a new Caribbean island, with enough time to explore the island and take in a sun-downer or sunset.

We make sailing the Caribbean and island hopping around the British Virgin Islands with a fully crewed private charter on a catamaran, so you have more comfort and a hassle free, relaxing vacation.

Get in touch and we can arrange your perfect Caribbean sailing holiday!

Med Sailing Holidays Offers Caribbean Adventures

Med Sailing Holidays is well known for making it easy for our guests to explore the most beautiful places in the Mediterranean Sea, but we also offer sailing holidays in the Caribbean. Experience the crystal-clear water, white sandy beaches, unforgettable sunrises and sunsets, and maybe even some pirate treasure in the British Virgin Islands on our fully crewed luxury yachts. We can cater to everyone, from couples to large groups and everything in between. If you want a private charter at your own speed and in seclusion, you can even charter a private boat complete with crew.

When Buying Caribbean Sailing Holidays Consider This

With the large variety of charter options we offer, there is something for everyone on one of our luxury sailing vessels. Make sure to pack light, bring a waterproof camera, and remember the following when you are considering a sailing holiday to ensure you get the most out of it:


  • You can charter a cabin on one of our public boats or hire a private charter with or without the crew. A private charter is an excellent way for groups to see the sites and set their own agenda. You can use one of our premade itineraries or create a custom one of your own.

  • Don’t forget about our special theme weeks. Our yoga sailing combines a yoga retreat, meditation, and a sailing holiday in one. With our Pride Sailing Holiday, our all gay crew will take you to some of the best hand-picked gay-friendly locations. For those more interested in what lies under the water, our dive week is an excellent opportunity to explore some of the hidden secrets buried in some of the most beautiful waters in the world.

  • Chartering a cabin on one of our larger boats offers more value with an unparalleled breakfast and lunch menu catering to vegetarians, vegans, and meat-eaters alike.

Things You Can Do While on a Bareboat Charter in the Caribbean

Our bare-boat yacht charter in the Caribbean is one of the best ways to get away from it all. For experienced sailors, you can charter the boat without a crew and be your own captain, island hopping and exploring the area at your own pace and in complete privacy. Perfect for couples or small groups that want to make the most out of their sailing holiday. Here are a few of our favorite places to suggest for you to explore with your bare-boat charter:

The waters surrounding the British Virgin Islands are a diver’s fantasy. You can swim along some of the flourishing reefs that pepper the ocean or explore some of the best shipwrecks in the world, such as the RMS Rhone. A Royal Mail Ship, it sunk on 29 October 1867 in a hurricane and is now home to a variety of wildlife.

The islands are home to many secret caves and grottos to explore. The Gorda Peak National Park is home to one such hidden cave, perfect for a secluded swim. As you sail near the Mountain Point dive site, there are mooring balls in front of the cave for your convenience.

At the end of the day, bring your chartered yacht in to land and sample some of the unique island cuisines, including some of the freshest seafood you will ever have. Most of the larger cities offer a variety of cuisines, but you can’t go wrong with the spicy and hearty local traditional foods.

About Med Sailing Holidays

We’re a privately-owned sailing holiday company that creates experiences catered to each guest. Our team has scoured the world and located the greatest sailing opportunities in places such as the Caribbean, Greek Islands, and Croatia. Join us as we take you to beautiful locations on secluded islands and get a taste of paradise on Earth. Contact us to book your private charter today. 


Virgin Gorda

Sailing British Virgin Islands highlights

  • Daily swim stops in the crystal clear Caribbean waters

  • Explore Islands and reefs only accessable by boat

  • Admire the pristine waters and perfect blue skies

  • Relax on the calm Caribbean waters as we island hop and slow things down to 'Caribbean Time'

  • Be welcomed by the warm hospitality of the locals

  • Snorkel coral reefs, plane & shipwrecks 

  • Swim & explore natural formations of 'The Baths'

  • Explore uninhabited islands

  • Search for Pirate Treasure on 'Treasure Island'

  • Ticking off a 'Bucket List' item; sailing the Caribbean!

What's included?

  • Seven days accommodation on your private yacht

  • BYO alcohol

  • Learn how to sail free of charge with your qualified skipper

  • Snorkeling gear

  • Your personal island guide with your experienced skipper

  • Port/marina charges and Yacht cleaning fee

  • National park fees, tourism taxes, search & rescue fees 

  • Drinking water, Diesel, Dingy and outboard engine

  • A private yacht for a fraction of the cost to do it yourself

We offer the most inclusions and the best value for money!



  • Tortola 

  • Marina Cay

  • The Baths / Devils Bay / Virgin Gorda

  • The Dogs / Cane Garden Bay

  • Sandy Cay / Jost Van Dyke 

  • Norman Island

  • The Indians / Peter Island 

  • Cooper Island

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Tortola is the largest island of the BVI chain and easiest to commute to.  


After setting foot on the island, reality will hit you, you've just landed in paradise.  


We always suggest you arrive a day or two early (if you can) to explore what the island has to offer and get accustomed to the slower pace of life.  


During your downtime you can explore the ancient ruins, take some sun at the beach or just enjoy the local cuisine before joining the boat.  

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Marina Cay

Marina Cay has a colorful past and collection of owners, including Jose Cuervo Tequila who purchased the island, referring to it as 'Cuervo Nation'


The island was used to host promotional events.  The island has a restaurant and bar, which as you'd expect offers the best rum.  The coral has amazing swimming before a well deserved rum.


Remember, drinking rum in the afternoon doesn't make you an alcoholic, it makes you a pirate. We will only plan to go here if we can leave the marina early!

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The Baths

On our way to Virgin Gorda, we take a swim stop at 'The Baths' which are rock formations which are millions of years old, that have created a famous swim, snorkel and beach. 


We will then head up to Virgin Gorda, which has always beena hit with travellers and boaties, as the island offers peaceful coves, safe anchorages and luxury resorts.  

We will take a mooring or anchor and explore the island for the best place to eat, drink, relax, swim, snorkel and whatever else you want to do, it's your holiday after all. 

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The Dogs

After leaving Virgin Gorda, we set off for the 'Dog Islands' where we'll drop anchor and you can snorkel and explore a large traditional coral reef and a plane wreck! 


We'll then make our way to Cane Garden Bay where you can enjoy the white sandy beach and relax with a drink, book or take up some water sports.  


Some amazing restaurants can also be found on the beach too.

Sandy Cay

We'll stop at Sandy Cay for breakfast and a morning swim.  You can wander to the north side of the beach and the 'Bubbly Pool' where is the swell is right, creates a bubbling jacuzzi.


The island Jost Van Dyke was named after an early Dutch settler and former pirate, we are in old Pirate Land after all.  


So we will take a mooring and explore the bays and the local legendary bars, Foxy's Bar and


The Soggy Dollar Bar that got it's name from people swimming to shore for a drink and pulling out soggy dollar bills from their swimmers.

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Norman Island

We will then head to Norman Island, which was named after a pirate who brought the island during the early 18th century. Normal Island or 'Treasure Island' is known for a long history of pirate booty being stowed on the island and legends of treasure being discovered here.  


The island offers caves for amazing snorkelling, hidden bays and wrecks that may still have unclaimed treasure!  


We will stay in a protected bay for the night and can check out the famous 'Willy T's' floating restaurant and bar or you can opt for a more relaxed time at the beach bar.

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The Indians

After leaving the bay, we'll go straight over to 'The Indians' for breakfast and you can enjoy an amazing rock formation and swimming spot. 


After our relaxing stop we will head to Peter Island where we will bay-hop, before settling in for the evening.  Walk around the island, explore the highest peak for stunning photos and remember to pinch yourself as you walk down the beach, this is the stuff dreams are made of!

Cooper Island
Cooper Island

Our first stop is at Salt Island, where beneath us you'll see the 'Wreck of the Rhone' which was wrecked in 1867.


Finally, we head for Cooper Island, which just like the rest of the trip is paradise.  You can swim down to Cistern Point, where you can snorkel and are likely to find Turtles, Octopus and other exotic sea creatures on a shallow dive.  


After a day of sun, swimming and relaxing you can have a final sunset cocktail with your feet in the sand and enjoy your last night on board, before we make the short trip back to base in the morning. 


When you book a sailing holiday in the British Virgin Islands, it’s important that you factor in all the running costs of the trip, so you have an accurate quote, you have the most value and you’re not surprised with unknown charges on the day.


If you are booking at sailing holiday for your friends and family in the British Virgin islands, you might want to consider a private charter so your group have the exclusive use of the boat. This way you also have more control over your in inclusions and overall trip.

The alternative to booking a private charter is booking a cabin charter. This way you get all the benefit of a private charter for a fraction of the price. It’s advisable to look what is included in the price, as much as what is not.


It doesn’t matter if you’re booking a private charter or a cabin charter for your British Virgin Islands sailing holiday, we include everything you could need on your trip. Because of this, at first glance our fully crewed sailing holidays may appear to be more expensive than the other operators, however you will discover that we offer more value for money, giving you more bang for your buck.