Sojourn Sailing focuses primarily on four Caribbean destinations, each with its own array of ancillary islands and ports of call to form an expansive, aquatic kaleidoscope of cruising options.

A yachting mecca and synonymous with all things tropical, the Caribbean offers charter yacht enthusiasts everything from deep tranquil bays and cays to a rich pallet of rhythm-filled nightlife. Throughout history, the Caribbean’s smooth waters, consistent winds and perpetual horizon have attracted boat and water lovers from across the globe, helping to sustain one of the world’s most eclectic cultural landscapes.

Even today, the Caribbean offers charter yacht customers endless opportunities for privacy through custom-designed adventures into little-known palm framed sandscapes and waterways. Away from the traditional hotspots, you will learn to love the tropics in ways you can’t experience from a hotel pool deck. Charter yachting opens you up to destinations that aren’t found on the pages of travel guides or in pre-packaged itineraries; these experiences are yours to explore. We just help you navigate them.


Puerto Rico and its sister islands of Culebra and Vieques are easily accessible, time honored cruising grounds for charter yacht guests. The smallest of the four Greater Antilles (along with Cuba, Jamaica, Hispaniola), Puerto Rico is popular for vast beaches that warm beneath a mountainous interior, making it an ideal stop for any island adventurer and nature lover.

While its mainland remains a common stop for commercial cruise lines, charter yacht guests can breeze into the island’s lesser-known locales to take in the parts of this vibrant United States territory that few get to experience. Puerto Rico may be widely known, but there is so much waiting to be discovered.

Twenty-one miles long and eight miles off of the coast of Puerto Rico, Vieques is a gorgeous National Wildlife Refuge that boasts some of the most attractive shorelines anywhere in the Caribbean. An ecotourism destination with little development, the waters off of Vieques offer your party the chance to anchor in privacy in one of its renowned bioluminescent bays for an evening of natural wonderment you’ll never forget.

Culebra, like Vieques, is also recognized as one of the Spanish Virgin Islands, although it remains a municipality of Puerto Rico. Tucked between its political parent and St. Thomas, Culebra is formed by its main island and a number of smaller islands that dot its sand and forested shoreline. With almost countless canals of Caribbean blue-green water to explore amongst the designated natural areas of its surrounding islands, Culebra is truly a locale in which you wouldn't mind getting lost.

Whether you want to anchor quietly off of the white sand solitude of Jost Van Dyke, the smallest of the chain, venture beneath the surface into the extraordinary spectrum of sea life in the legendary reef just off of the island of Anegada or explore treasures of a different kind along the boutique-rich streets of St. Thomas, we highly recommend a sojourn through the Virgin Islands.

The Virgin Islands, collectively, consist of the U.S. Virgin Islands (USVI) of St. Thomas, St. Croix and St. John and the British Virgin Islands (BVI), primarily defined by Tortola, Jost Van Dyke, Virgin Gorda and Anegada. The USVI was purchased from Denmark in 1917 for $25 million in gold and its people are citizens of the United States, thus, you do not need a passport to visit the USVI. The BVI is considered a non-Sovereign, overseas territory of the United Kingdom and therefore entry into island communities does require a passport. The primary currency, however, is the US dollar.

We can arrange yacht charters into your favorite harbors or help you experience the more secluded sections of sea surrounding these naturally chromatic island sanctuaries.

Rich in culture, architecture and artistry, the United States Virgin Islands (USVI) have become known worldwide as a must-see destination for yacht charters, especially during the month-long Carnival celebrations that ignite each island in their own din of dance music and raucous parades.

Off of the islands' coasts floats a different setting. From the deck of your charter yacht, quietly toast a stunning sunset that back-lights a foreground of remote islands or wake up to a gentle Caribbean wind running across a placid cove that for one incredible night, you called home. The boundary waters of the USVI boast incredible snorkeling and diving opportunities and more importantly, you can experience the rich reefs and coral life in the company of just your family or friends, away from the cruise crowds and day-trippers.

Take in St. Thomas, St. John and St. Croix in ways your parent’s travel agent never thought possible. Let Sojourn Sailing help you check off from your life-list a Caribbean adventure like no other in and around the aquatic paradise of these magnificent tributes to the power of natural beauty.

While the British Virgin Islands (BVI) are technically made up of 60 islands, Tortola, Jost Van Dyke, Virgin Gorda and Anegada remain its primary destinations — and with good reason.

To cruise the waters of the BVI is to experience what it truly means to be on your own yacht. Narrow, vibrant teal channels wind through intimate island settings leading to secluded anchorages where on-deck dinners are made to order and the sun sets just for you.

On your approach to Tortola, the largest in the chain, you’ll witness a mountainous, heavily-forested interior provide wild contrast to the serenity of the white sand beaches that sprawl at the foot of its canopy. You can cruise into popular but beautiful areas like Cane Garden Bay before the island is awake or spend the afternoon floating through the incredible snorkeling grounds of Brewer’s Bay or Smuggler’s Cove. For the more active in your party, consider tracking down a swell in one of Tortola’s surfing spots, like Josiah’s Bay.

After a night or two in and around the dazzling waters of Jost Van Dyke, you’ll understand why this smallest BVI locale has the reputation it does. Considered by many to be the last bastion of old British Virgin Island culture, Jost Van Dyke extends a welcoming vibe and canvas-ready Caribbean backdrop that few forget.

Virgin Gorda and the remote north shore beaches of Anegada also offer a tremendous array of Caribbean sailing highlights. In Virgin Gorda, explore the Baths, a series of boulder-lined pools that sit adjacent to soft, expansive beaches or anchor off of Trunk Bay for more snorkeling and beach gazing. And while difficult to access, Anegada’s Horseshoe Reef offers some of the best diving found in the world and if you want to just grab a drink on shore, stop into the Big Bamboo, a palm-roofed hideaway perfect for swapping half-truths and tall tales.

Sojourn Sailing can also ensure you get to explore the multitude of additional islands that link together the BVI, just give us a call and we'll start planning.

The northern component of the Lesser Antilles, the Leeward Islands are a fantastic collection of Caribbean islands that could provide months of charter yachting adventure. Exceptional scenery, engrossing cultural diversity and quintessential tropical marine geographies await all those who visit these breathtaking island environments.

The group of islands making up the Leewards are so deemed because they are leeward, or downwind, of their equally visually impressive sister chain and Sojourn Sailing destination, the Windward Islands.

The Leeward Islands are made up of Anguilla, Saint Martin/Sint Maarten, Saint Barthelemy, Saba, Sint Eustatius, Saint Kitts, Nevis, Antigua, Barbuda, Montserrat and Guadeloupe. The territorial affiliations range from the United Kingdom, France and The Netherlands. However, Nevis and Saint Kitts independently form The Federation of Saint Kitts and Nevis while Antigua and Barbuda are a single island nation.

Regardless of political affiliation, the Leeward Islands offer you a virtually endless selection of unique island ports, secluded anchorages and an unlimited supply of Caribbean horizon views.

Whether you want to explore the serenity of Nevis, “Queen of the Caribees,” stop into the busy streets of St. Martin, anchor in a cove off Montserrat’s south shore to view the astonishing Soufriere Hills volcano or explore the quiet shores of Saba, which is the least visited of the Leewards, Sojourn Sailing can arrange an itinerary that will unquestionably justify every reason why you decided to charter this year. Here is a map of the Leeward Islands.

The southern sister of the Leeward Islands in the Lesser Antilles, this remarkable chain of paradise personified is a popular destination of boaters worldwide. And why shouldn't it be?

Helping to form the eastern border of the Caribbean sea, the Windward Islands are commonly thought of as Martinique, St. Lucia, St. Vincent, Bequia, Mustique, Canouan, Mayreau, the Tobago Cays, Union, Palm Island, Petite Saint Vincent, Grenada, Carriacou and Petite Martinique. Some travel guides vary in their definition of the island set but since Sojourn can arrange for you a trip through each of their accompanying vistas, consider this a reputable list.

Popular settings like St. Lucia and St. Vincent have without question earned their reputations and are ideal for family charters seeking familiar tropical settings. Both islands offer scenic and natural escapes from the commercial tour and cruise crowds. To discover the more obscure but extraordinary settings of the Windwards, steer your captain toward one of the deserted Tobago Cays for snorkeling sights more vibrant than any HD TV on the market today or anchor near the storybook locale of Sandy Island, perhaps the only source of inspiration a motivated adventure novelist would ever need. You can also visit the traditional, quaint Port Elizabeth on Bequia to get a feel for an authentic Caribbean boat village that attracts exclusive charter guests from around the world.

The Windward Islands are true island sanctuaries for the charter group weary of the typical annual get-away. In their waters and upon their shorelines you will find solace, a new appreciation for the ocean and more than a thousand reasons to never leave the Caribbean.

Sojourn Sailing can help you explore regions that the guide books miss and the locals covet. Tell us about your dream charter yacht vacation and we'll show how to make it reality in the Windwards.

Take a look at this map to better understand the Windward Islands.

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Captain Dare Blankenhorn

Leigh Ann Nelson