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Chartering in the Caribbean

Caribbean Sailing

Seamanship Article Index


Chartering in the Caribbean & Bahamas

Caribbean sunset.
Photo copyright (c) 2005 Daria Blackwell.

Where you go may have a direct relationship with how much time you have and how comfortable you are chartering. Some of the islands are a little more difficult to reach. Others are a snap with daily direct flights from the US . Some of the islands have gentle winds, calm seas, and easy navigation. Others offer greater challenges. First time charterers often choose the Virgin Islands because they are easy to get to and easy to sail. Let’s examine some of the options. 

British Virgin Islands

Sailors find these islands appealing because the waters are relatively calm, the anchorages appealing and varied, and the islands are usually no more than 2 or 3 hours’ sail apart. There are many charter boats available there, and a great maritime history full of stories of pirates and treasure. 

Tortola is the largest and most populated of the islands with about 14,000 residents and also one of the primary charter bases in the BVI. Tortola has mountain peaks covered with sage and frangipani along the southern coast, and white sand beaches, palms, mangoes, and bananas along the northern shores. Sage Mountain National Park has many characteristics of a tropical rainforest. Road Town , the capital of the BVI, is on the south shore.

BVI. Photo copyright (c) 2005 Daria Blackwell.

Virgin Gorda, a lush tropical island with the beautiful North Sound and home of the Bitter End Yacht Club, is a great destination. It has a population of about 2500. The northern end has a good-sized peak while the southern half is flat with giant boulders. The Baths – a series of pools and grottos for snorkeling and swimming – are here. There are some 20 beaches on Virgin Gorda and the sailing is extraordinary. Anegada, completely different from the others, is a coral island with a population of 150 and a height above sea level of only 28 feet. It offers endless sand beaches and a horseshoe reef for diving and snorkeling. Marina Cay offers excellent snorkeling as well. 

US Virgin Islands

Like the BVI, these islands are relatively close to each other, diverse in what they offer, and a base for several large charter companies. St. Thomas is the hub, and a major port in the Virgin Islands , offering massive tourist activities and shopping opportunities. 

St. John , the smallest and least populated of the islands, has lots of bays and inlets. Since roughly two-thirds of the island is national parkland, St John has a natural unspoiled feeling. At several beaches on the North shore, you can just wade in to go snorkeling to your heart’s content. The underwater trail at Trunk Bay is often crowded but great for kids, while the submerged landscape at the base of Waterlemon Cay will leave you in awe.

St. Croix , 40 miles South of St. Thomas, is more of a residential island. It provides a good jumping off point for access to Buck Island Reef National Monument , the only underwater national monument in America , offering a snorkeling trail that snakes its way over coral canyons that harbor colorful tropical fish. 

St. Lucia from Martinique
Photo copyright (c) 2005 Daria Blackwell.

St Lucia and Martinique

Mountainous and lush, St Lucia, this jewel of the Windward Islands, is a steep volcanic island where the twin peaks of the Pitons rise more than 2000 feet from sea level. Sailing excursions here last from three to six days, usually involve island hopping down the chain, and a wide variety of charter packages are available. The great thing here is the distinct flavor of foreign lands. For example, you might visit Fort de France, the Paris of the Caribbean then sail to Grand Anse d’Arlet to snorkel near a fishing village. Near Martinique , the waters are especially clear, with plenty of bright tropical fish and corals.


Dominica is the island paradise in the Caribbean. It has 365 rivers, eight volcanoes, and only 70,000 people. It is one of the largest islands yet the least built up. There is no international airport...yet! We had heard that is the only truly unspoiled island in the Caribbean , the only island Columbus would recognize if he arrived back today. We desperately wanted to visit. Yet, we had also heard there may be problems with security, so we approached cautiously given previous experience on other islands.

St. Vincent and the Grenadines

This is a fabulous place to sail with beautiful lush terrain, West Indian culture, and favorable conditions. 

You could sail all the way from Bequia (pronounced bake-we), the island of clouds, to Grenada if you wanted. You’d certainly want to make a stop in the Tobago Cays which are the national marine park of St. Vincent and the Grenadines . About 50 miles from St. Vincent, these uninhabited islands offer a lovely serene anchorage and great snorkeling. You might want to unwind first on Bequia, a former whaling port, where an anchorage on the north side offers access to beaches and snorkeling. Mopion, a tiny uninhabited sand spit, lies a short distance off. Click here to view an illustration of the Windward Islands group.


Guadeloupe offers easterly trade winds, line-of-sight sailing, open water cruising, amazing rainforests and underwater preserves, all rolled into one exhilarating destination. All nine islands of this chain differ in size and topography making them a popular sailing destination, albeit perhaps a bit more challenging to navigate than the Virgin Islands . The French island of Guadeloupe itself is formed of two parts, Basse Terre and Grande Terre, that combined look like a butterfly (from which the name is derived) whose wings are separated by “la riviere salee” (the salty river). The city of Point-a-Pitre , established in 1654 and the economic capital of Guadeloupe , is the staging place for many foreign visitors.

Grenada. Photo copyright (c) 2005 Daria Blackwell.

Basse Terre

Basse Terre is home to the Soufriere volcano. The leeward coast is considered by many to be the most beautiful part of Guadeloupe . It is covered by dense rainforest leading down to black sand beaches. The snorkeling here is unparalleled in that the spectacular colors of the fish are especially vibrant against the black sand backdrop. Baie de Pont Pierre is breezy but protected, with a choice of anchorages on two ends. The anchorage formed by the reefs between the two islands of Iles de la Petit Terre, is especially picturesque; although anchoring is not permitted, there are moorings available for visiting sailors. These islands are a nature reserve with a richness of flora and fauna and a great vantage point for viewing the southern coast of Grand Terre .

Marie Galante

Marie Galante, only 3 to 4 hours from Petite Terre, offers numerous anchorages, white sand beaches, and the charming town of Saint Louis where you can find restaurants and shops. Another 3 hours downwind is Iles des Saintes, a hilly grouping of tiny islands just a few miles from Guadeloupe. The bay of Les Saintes is considered by some to be the most beautiful bay in the world. You can spend several days here exploring the magnificent coral beds off the Cabri Islets or exploring the town of Terre de Haut . For diving enthusiasts, the reefs between Pain de Sucre beach and Les Bois Joli offer great divisng as does the Cousteau Underwater Park .


Barbados is known for its beautiful beaches, expansive mansions, and lavish parties. There are highly competitive cricket matches and lots of famous inhabitants and visitors, but the facilities for visiting yachts are limited. Nevertheless, Barbados, though technically outside the Caribbean Sea, is one of the closest destinations for yachts crossing the Atlantic for the winter season and worth a visit.

Belize. Photo copyright (c) 2005 Daria Blackwell.


Many people do not think of Belize as part of the Caribbean, but it most certainly is. In fact, most of the Central American countries border the Caribbean, but Belize has something the others do not. It has the second largest barrier reef outside of Australia, which includes plenty of small islands and cays to sail around. It also has some of the best diving and snorkeling in the Caribbean, including a black hole. In fact, the cruising territory covers Belize; Rio Dulce, Guatemala; and Bay Islands, Honduras - over 3,000 square miles. Hundreds of islands, cayes and coral reefs make this area perfect for tropical sailing adventures but also present numerous challenges to navigation. Experience is the key to enjoying a safe and memorable sailing vacation in Belize. Charter packages can include bareboat sailing to a destination where a dive boat can meet you for a personal adventure. Ambergris Caye is dive central, while Placencia - where the Garifuna, Creole and Mayan cultures intersect - is the sailing charter center for Belize.

For more information about the coast of Belize, visit


Abacos. Photo copyright (c) 2005 Daria Blackwell.

The Abacos

Though less popular than many other charter destinations, the Abacos offer an amazing cruising experience outside of the Caribbean. At the northernmost end of the Bahamas , the Abacos are a chain of islands strung together within eyesight of one another. Marsh Harbor , the main town on the largest of the islands, is home to a Moorings base and provides access to these intriguing islands, each of which has a distinctly different character. The Abacos were settled by Loyalist refugees escaping the newly independent United States in the 1700s, and their population continues to be primarily the descendants of these early settlers. 

The major islands of this small archipelago are Great and Little Abaco. The main cays strung out over 120 miles are Elbow Cay, Man-O-War Cay, Green Turtle Cay, Guana Cay, Stranger’s Cay, Umbrella Cay, and Walker ’s Cay. Grand Cay was once a favorite of Richard Nixon, and Pelican Cay is home to an underwater preserve. Elbow Cay has beautiful beaches on the ocean side and a candy-cane striped lighthouse guarding its picturesque Hope Town harbor. Man-O-War Cay is known for centuries of shipbuilding, which continues by traditional methods without plans today. The town here resembles a New England seaside village, the harbor is sheltered, and there are some provisioning options. Green Turtle Cay has a turtle farm that serves as a local food supply, and Guana Cay has a nice little beach resort worth a visit. There are also plenty of protected anchorages off uninhabited cays where the yachtsman can find solace in a good book and glass of wine

Click here to view a map of the Caribbean. (pdf)
Plan your cruise around other activities you might like to try, like diving, parasailing, windsurfing, snorkeling, hiking, and visiting ruins.
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Click here to view the Coastal Boating Top Ten Ways to Charter List.

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