US and British Virgin Islands Sailing Vacation MapVirgin Islands sailing vacation includes sailing and motor yacht charter trips that include Catamaran charters, monohull sail bareboats, crewed charters, super yachts, motor yachts and VI sailing holidays are among the best in the world!

Why a Virgin Islands sailing vacation is among the best:

  • Perfect sailing trade winds and protected anchorages
  • Natural beauty on the islands and below the water
  • A vibrant modern culture with a unique Caribbean history
  • Privacy, party island style and easy to fly to while safe to visit.

Read more about the many activities a USVI and BVI Yacht Charter has to offer below or

see a Sample Itinerary of a Virgin Islands Sailing Vacation 

Virgin Islands Sailing vacation catamaran
Virgin Islands catamaran sailing

Sailing Conditions

Through a unique combination of geology and geography, the US and British Virgin Islands BVI boast some of the best sailing charter grounds in the world with steady trade winds, averaging 10-15 mph from the northeast, with insignificant currents and tidal range. There are almost 100 islands and cays (also pronounced keys) in the Virgin Islands (USVI and BVI) that are a short sail from one another.

The Virgin Islands offer protection from ocean swells and provide hundreds of protected coves and anchorages (many of which have moorings to protect the bottom life from damaging anchors) for swimming, snorkeling, diving, going ashore, or just lounging on the boat.


Virgin Islands Sailing vacation BVI
Virgin Gorda Baths, British Virgin Islands BVI

The natural world of the Virgin Islands is one of its greatest draws. The islands are mostly volcanic in origin, although they have been extinct for millennia, and are fringed with limestone from eons of coral growth. Most islands have quite dramatic landscapes, the larger islands with peaks over 1000 feet, the highest point being Sage Mountain on Tortola which is 1780 feet.

Aside from the islands’ stunning beauty as you are sailing past, a closer look will reveal a multitude of subtropical ecosystems including mangrove swamps, coastal dry forests and even small patches of rainforest. Despite centuries of deforestation for agriculture, these ecosystems support a wide variety of tropical flora including numerous flowering plants and trees such as the gumbo limbo, mahogany, flamboyant and many cultivated fruit and shade trees. Even ‘magic mushrooms’ grow wild and are legal to consume in the British Virgin Islands. See  also the amazing Virgin Islands Scuba Dive Sites.

Virgin Island Iguana
Virgin Island Iguana

The islands’ fauna, or animal life, includes mammals such as deer, wild donkeys, goats and mongoose (introduced), reptiles (including anole and gecko lizards and the famous 6 foot long rock iguanas of Anegada), insects (yes indeed) and birds.  Over 200 species of birds have been accounted for in the Virgin Islands including songbirds, migratory waterfowl, seabirds and the ubiquitous bannaquit or ‘yellow bird’.

Virgin Islands Sailing vacation snorkeling BVI
Sailing snorkeling BVI Queen Angel reef fish

Much of the Virgin Islands’ animal life however is found beneath the surface of the water, most notable are the coral reefs that fringe each island. The clarity of the water and the shallow depth of many of the reefs provides world class opportunities for viewing this extraordinary ecosystem by snorkeling or scuba diving. In addition to the numerous reef species and tropical fish you will inevitably have a chance to view, not uncommon sightings of manta rays, nurse sharks, barracudas, octopuses, moray eels and several species of endangered sea turtles while snorkeling the stunning Virgin Island waters.

History and Culture

The abbreviated version of the Caribbean Virgin Islands history goes something like this:

  • 2000BC North American Indians arrive and settle the islands
  • 100AD Other Indians arrive from South America
  • 1493 Christopher Columbus ‘discovers’ (but does not settle in) the Virgin Islands on his second voyage to the New World and names them after St.Ursula and the 11,000 Virgins (a 4th century princess raped and murdered by the Huns).
  • 1595 Privateers hired by European rulers (known to the world as pirates) begin using the Virgin Islands as their home base.
  • 1621 English, Dutch, French and Spanish colonists fight over and occupy the islands for growing crops, including tobacco.
  • 1700’s Africans are brought to the Virgin Islands as slaves work the sugar and cotton plantations.
  • By 1848 when slavery becomes outlawed, some 220,000 Africans had been brought to the Virgin Islands and forced into slavery.
  • 1917 The United States buys St. Thomas, St. John and St. Croix from Denmark for $25 million.
  • 1950’s The Virgin Islands begin to market themselves as a tourist destination forever changing the economic structure of the islands.
  • 1960’s The US forbids its citizens from visiting Cuba and jet travel becomes common, resulting in a massive influx of American tourists to the Virgin Islands.
  • 1967 The BVI became an independent British colony.
Virgin Island culture
Virgin Island culture

Today the culture of the Virgin Islands is uniquely its own, with hints of American, British and West African. As you meet locals you will undoubtedly realize that most people are very social, placing strong value in their families, friends and community and that they absolutely love their islands and way of life.   The people are also very polite, something most Americans are not used to.  If you take the time to greet people with a ‘Good morning’ or ‘Good afternoon’ you will get much further in your social interactions with locals.

The arts are very alive in the Virgin Islands including several original styles of music, painting, crafts, and of course the Afro-Latin music mixes. The islands additionally enjoy the highest per capita income ($13,000) in the Caribbean and their modern economy is primarily based on tourism, with some manufacturing.

Virgin Islands Sailing vacation beach bar music
Virgin Island Live music charter!


The Virgin Islands are legendary for their good times and the continuous celebration of life usually includes all classes and races mixing as easily as the blender drinks do. You will find yourself partying with other yachters, local islanders, the rich and famous and backpackers. If you like dancing barefoot in the sand to great recorded and live music, the island’s beach bars are for you.

World famous beach bars include Foxy’s Tamarind Bar (Jost Van Dyke, BVI), Bomba’s Surfside Shack (Tortola, BVI) and the Schooner Willie T’s (Norman’s Island, BVI) and countless others. Make sure you try the various island concoctions like Painkillers, Rum Punches and everyone’s favorite, Pina Coladas! Things get especially wild on full moon nights! Beware the Magic Mushroom Tea in the BVI.  Good thing you have a yacht standing by.

Activities  on a Virgin Islands Sailing Vacation
snorkeling Virgin Islands
snorkeling in the Virgin Islands

There are sooo many. Here are a few favorites. Swimming, snorkeling and scuba diving: In addition to all the glorious sailing you will be doing on your trip, chances are one of your main goals of visiting the Virgin Islands is to enjoy swimming, snorkeling or scuba diving in the warm water. You will not be disappointed. You can swim from your yacht anytime and the beaches in the Virgin Islands are all open to the public (except on a few private islands).

The Virgin Islands also offer exceptional snorkeling in shallow calm waters and over 100 outstanding dive sites. The water is exceptionally clear (visibilities exceeding 100 ft) and temperatures range from 76-84°F (24-29°C) year round. Your yacht will provide you with snorkel gear and instruction and will bring you to their favorite snorkel spots. For you scuba divers, some yachts have their own dive gear and air compressors, others can easily arrange for a dive boat to pick you up at your yacht and take you diving. See the Nature section above to learn about what you may see in the waters of the Virgin Islands.

windsurfing Virgin Islands
windsurfing Virgin Islands

Surfing and Windsurfing: The winter months bring steady swells to the exposed sides of the islands, and the surfing community knows just where to catch the waves. Windsurfing is also very popular in the Virgin Islands and some yachts carry their own windsurfers on board. Contact us to find out which ones specialize in these water activities!

Fishing: Several of the yachts we represent carry fishing gear and you can try your hand at catching dinner. Dorado or mahi mahi are common throughout the winter, marlin in the summer, and sailfish and wahoo in the fall.

Hiking: The Virgin Islands are a mecca for hikers, especially the 23 miles of hiking trails in the 9500 acre Virgin Islands National Park on St. John.

Bird Watching: Bird lovers will delight in the diversity and abundance of bird life the Virgin Islands has to offer. The best spots being the salt pond of St. Croix and Anegada and the mountain tops of St. John and Tortola.

Virgin Islands Sailing vacation
Virgin Island vacations


When you need to get away from it all, the Virgin Islands offer numerous secluded anchorages and quiet white sand beaches. All beaches in the Virgin Islands are open to the public, and there are many to choose from especially if you are traveling by yacht. With all that privacy you may want to go natural.

Many yachts are comfortable with their guests going in the raw and offer clothing optional nude sailing vacations.

Practical Reasons for a Virgin Islands Sailing Vacation

In addition to the numerous undeveloped and natural islands, St. Thomas and Tortola are well developed with all the amenities you can hope for.  Some practical reasons for setting your vacation in the Virgin Islands include:

  • Major international airports and several daily flights to the US.
  • Excellent medical facilities.
  • All islands use the US dollar as currency.
  • English is the official language of the Virgin Islands
  • The islands are generally very safe and have first world hygienic and law enforcement standards.
  • Lots of services that you as a traveler may need, including internet cafes, drugstores, etc.
  • Great duty free shopping opportunities.

Browse the available crewed sailing and motor yachts for a Virgin Islands Sailing Vacation with a Yacht Search.

Sample Itinerary of a Virgin Islands Sailing Vacation 

Virgin Islands Maps and Travel Information

Other Caribbean Yacht Charter Destinations

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