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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.

Marina Cay


Spend your first night in Marina Cay where you ca eat dinner and enjoy the sunset.


Jost Van Dyke


Its stunning white sand and clear turquoise waters, perfect for swimming & sunbathing, 

Virgin Gorda The Baths


We'll enjoy 2 legendary locations today, Foxy's and Soggy Dollar Bar.

Norman Island Sailing charter


The island offers caves for snorkelling, and wrecks that may still have treasures.



Go for a hike, drink rum, and see the Smugler's Cove Beach in just a day.

Cooper Island Sailing holidays


Also know as the "Salt Island" where beneath you'll find the 'Wreck of the Rhone' which was wrecked in 1867.

British Virgin Islands Itinerary
British Virgin Islands


Everything you need to know on how to get to BVI coming from your designated locations.

7 Days   Private Charter

Kalamos Greece
Enjoying on the boat
Greece, Pebble Bay
Ionian sea


Our carefully crafted itinerary seamlessly blends with the breathtaking landscapes of the BVI. Enjoy activities like snorkel in crystal-clear waters, beach bar hopping, and exploring local attractions.



Marina Cay Tortola

Check in time is 5 PM at Tortola Marina

You will be greeted by the crew and will have a glass of Proceso waiting for you upon arrival at the boat.


Virgin Gorda

Sailing Holidays

We will then head up to Virgin Gorda, which has always been a 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. 



Island Hopping

Anegada is a small island furthest north in the British Virgin Islands.  Anegada is known for it's lobster, so get in early and pre-order your lobster on the BBQ. Once you've got your lobster order sorted, it's time to explore! hire a scooter and ride the island in no time, keep an eye out for the pink flamingos and we wont blame you if you stop for a cheeky cocktail on the way.


Jost Van Dyke

White Bay, Jost Van Dyke

Jost Van Dyke is the home of two famous establishments; Foxy's and Soggy Dollar Bar. Soggy Dollar Bar is on the picture-perfect 'White Beach' that is the perfect backdrop for afternoon 'painkiller' cocktails and swimming. The evening is for Foxy's where you'll enjoy some amazing local food and entertainment. Get ready to dance the night away!


Frenchmans Cay

Enjoying the sunset

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.


Norman Island

Peter Island yoga sailing

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

Sailing Holiday

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.

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.



Sailing Holiday

Return to base.



Lefkas Sivota

Saturday: Check out at 10am.

Sadly it's time to say good bye, until next time

Please note the itinerary may change without notice due to weather, sailing regattas or other reasons. Departure on Saturday, providing no significant boat damage from previous week.

Catamaran charter


Here is our Lagoon 42 up close. Look how beautiful it in the cobalt blue ocean.


Introducing our beautiful Lagoon 42. This catamaran is one of the best models in the industry and is popular choice for sailing holidays.

Forward cabin


These cabins are situated on the front part of the catamaran. It's not as big as the Master but some couples prefer it here. 

Master cabin


These cabins are situated on the rear part of the catamaran. It a bit bigger than the Forward cabin and is more for shared charter.


You're greeted with Champagne upon arrival


Seven days/nights accommodation on your luxury private yacht


Half board: your hostess will prepare your breakfast & lunch


Full friendly crew: Skipper & hostess. Learn how to sail or test your skills with your qualified skipper.


All your onboard costs included: Your weekly marina & port fees, *fuel, final cleaning fee, tourism taxes.  No hidden charges or 'departure taxes'.
*fuel paid at end of week for private charters

wine bottle

Bring-Your-Own (BYO) alcohol.


We also have a Snorkeling gear on board for your usage.


Crew dinners and fuel are excluded  for private charters

Hydra Beach


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


Greece swim stop


Everything you need to know on how to book your med sailing holiday trip. It's very simple, it'll make your booking as "smooth sailing" as possible.


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!

Sail the Ionian
Sailing on a catamaran

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. 

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