Caribbean sailing yacht vacation

The US and British Virgin Islands with balmy sailing breezes and warm waters year round are arguably one of the best sailing vacation destinations in the world. “Line of sight” navigation, protected deep clear blue water, numerous beautiful bays and breathtaking palm fringed beaches, exciting snorkeling and many “interesting” bars and restaurants make these islands a must see. An experienced crew, with important local knowledge, will take care of those, wanting to really enjoy a relaxing and safe holiday on a Caribbean sailing vacation.

Start and end your Virgin Islands sailing vacation in St, Thomas, US Virgin Islands (airport code STT) and visit the US (St, Thomas, St, John) and the British Virgin Islands (Tortola, Virgin Gorda, Jost van Dyke, Peter Island, Norman Island etc), Or start and end in West End, Tortola, BVI Beef Island (airport code EIS) to visit the northern part of the BVI like Marina Cay, North Sound Bitter End, Anegada, Dog Islands, Virgin Gorda etc. A relocation fee may apply.

Caribbean sailing yacht vacation itinerary cruising the US and British Virgin Islands

1st day:

We welcome you aboard the sailing yacht BILLY JEAN at 2:00 pm and explain to you all the things you have to know about “living aboard”. Set sail to St. John, anchor in Francis Bay, St. John and have your first swim and snorkel in the blue Caribbean waters.

sailing vacations st.john


2nd day:

After breakfast we head to West End Tortola, Soper’s Hole to check into the BVI waters. You have the opportunity do do some shopping ashore. After lunch we sail towards Cooper Island. The Cooper Island Beach Club is known for his excellent tropical drinks. Dinner al fresco in the protected cockpit of Billy Jean after the sunset ends another beautiful day in paradise.

caribbean sailing vacation cooper island beach

3rd day:

One to two hours of sailing will bring us to Virgin Gorda, where we dock in the marina of Spanish Town. From here to take a taxi to The Top of The Baths and explore one of the most unique site in this area: the Devils Bay trail through The Baths.

destination virgin gorda the baths sailing vacation

4th day:

In the morning you can take a short walk to one of the most exclusive resorts on Virgin Gorda: Little Dix Bay. You are welcome on their palm fringed, picture perfect beach for launching and sunbathing and for a drink, of course. We leave the marina after lunch for a nice down wind sail to Peter Island.

sailing cruise to peter island resort virgin islands

5th day:


A short sail brings us to Norman Island, The Bight. You can take the ocean kayak for a ride to the snorkel spot The Caves.

snorkeling sailing vacation norman island the caves

We moore close to the world famous swimming bar and restaurant Willy T’s (William Thornton). For the more adventurous type: you can experience a “body shot” and get (temporary) tattooed with the Willy T’s skull and Bones.

party boat willy ts norman island sailing vacation

6th day:

With the wind from behind we have a nice sail to St, John and pick up a mooring in one of the national park coves, Leinster Bay. This is a very quiet place with Waterlemon Cay as an excellent snorkel spot. Because there is no artificial light at night it makes also one of the best spots for stargazing.

snorkeling spotted eagle ray sailing vacations caribbean

7th day:

We set sail to Cruz Bay, St, John where we check back into US territory. We have lunch ashore at “Woody’s”, famous for their Hamburgers. We then head back to St. Thomas and pick up a mooring in Christmas Cove. More snorkeling and another perfect sunset await.

caribbean sailing vacations

8th day:

After breakfast you will have to say good bye to BILLY JEAN, your swimming home for the past week. We are sure that you will have had an unforgettable week.

sunset caribbean sailing vacations

This example is just one of the numerous ways to see the islands. Some times we also visit Jost Van Dyke with the famous beach bar FOXY’S or we show you more of the national park of St, John. The final itinerary is made according to your needs and depending on the actual weather conditions. The final decision is always made by the captain.

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Make the captain only sailing yacht Billy Jean your destination for Caribbean sailing vacations.