It’s impossible to compare and describe all the Caribbean islands since there are over one thousand of them. However, this review will focus on six of the most famous destinations: the Bahamas, the British Virgin Islands, Cuba, Belize, and the Leeward and Windward Islands.
Christopher Columbus was the first European to sail across the Caribbean Sea over half a millennium ago. He raved about the countless large and small islands, including Cuba, the Bahamas, and the Antilles. Later, colonial powers like the Dutch, British, French, and Spanish took control. Most island states are independent today, but their colonial influence remains, especially in language and culture. English is spoken on almost all Caribbean islands, although only Belize has it as the official language.
The variety of tastes, attractions, and customs in the Caribbean is incredible. Some islands are famous for rum and reggae, while others boast baguettes and lattes, or an exclusive cigar. However, all the islands share the unforgettable Caribbean flavor of turquoise water, tropical temperatures, and colorful underwater worlds. The warm trade wind is probably the best and most reliable wind system a yachtsman could wish for, and most places in the Caribbean fulfill the dream of palm trees and white sandy beaches.
Each direction in the Caribbean has its own unique characteristics. Some archipelagos, such as the Bahamas or the British Virgin Islands, are large enough to constitute a separate nation. These destinations, along with Belize in Central America, are well-protected from the great Atlantic storms. Conversely, in the Antilles chain between Saint Martin and Grenada, each island is a separate state. Crossing borders and discovering island nations that are completely different from each other is an integral part of the sailing experience in the Caribbean.
One of the features of the Caribbean Sea is its pronounced seasonality. The high season is from November to April when the conditions are ideal for sailing: steady trade winds from the east, little rainfall, and no hurricanes. Ocean swell is also not a problem thanks to the cover of the islands.
However, it’s important to choose a sailing area that best suits the crew’s experience and goals, especially when chartering a yacht. Otherwise, disappointment can’t be avoided.
From the descriptions above, you can determine which destination to choose and what features sailing conditions, and charter options are available.
Bahamas
Navigation Area
Of the more than 700 Bahamas islands, only three dozen are inhabited. The most accessible and interesting neighborhoods are located on two of them – Great Abaco and Great Exuma. The water area near Great Abaco is well-protected from ocean swells, with bars scattered along sugar-white beaches. The island has many towns, luxury resorts, and marinas. On the other hand, the southern waters of Great Exuma are more secluded, offering peaceful anchorages where you can escape from the crowds. This luxury is rarely found in the Mediterranean Sea. Many anchorages on these islands are ideal for keelboats, although some are not available for larger boats.
These main charter sailing areas in the Bahamas are located about 200 nautical miles apart, so visiting both during a single trip is only possible during a long journey. Within each water area, the distances between parking spots are small, although they can be increased if necessary. You are guaranteed calm seas behind the chain of islands, which is important since you will be sailing almost exclusively in shallow areas with beautiful turquoise water. Swimming in this area is relatively easy, so it can be safely recommended to yachtsmen without much experience who want to explore exotic seas.
Charter in the Bahamas
In the north of the archipelago, the main bases of international charter fleet operators such as Moorings, Sunsail, and Dream Yacht Charter are located in Great Abaco. On the southern side, sailing can be started either from Nassau or directly from Great Exuma. Regional airports here offer connections to Miami in the US, but many scheduled airlines fly directly to Europe.
Cuba: A Navigational Guide for Adventurers
Sailing in Cuba is an exotic adventure that appeals to those who seek an off-the-beaten-track experience. The primary route starts from the charter base in Cienfuegos and heads towards the chain of islands located in the south of the country. There are reportedly more than a thousand small islands, known as “cayos,” in shallow waters filled with reefs, which require careful navigation. Unfortunately, the cartographic coverage of this area is not up-to-date, and yachting infrastructure, such as ports, beach bars, or restaurants, is only available in a few locations. Nonetheless, Cuba is a true paradise for nature lovers, anglers, divers, and lobster enthusiasts who are willing to put up with some restrictions. A sailing holiday in this region is more of an expedition than a typical charter trip with all its comforts and conveniences. Therefore, it is not recommended for yachtsmen who lack proper experience. However, there are plenty of beautifully secluded anchorages that can be explored.
Charter sailing in Cuba always starts in the third largest city of Cienfuegos, situated on the south coast of the main island, as there are no charter bases in other locations. Most crews head west from there towards the Canarreos archipelago, where the route length within the entire archipelago can reach almost 400 nautical miles, offering a wide range of destination options. The places here are quite developed, with marinas, anchorages, hotels, and restaurants. Alternatively, a journey to the east towards the archipelago known as the “Queen’s Gardens” offers a completely different experience, as it is an ecologically pristine paradise of small, almost untouched islands, coral reefs, and magnificent underwater life. One should not miss the opportunity to spend at least one day in Havana to experience the vibrant life of this city that will be remembered for a long time.
Charter in Cuba
There are limited options for charter providers in Cuba, with all offers located in Cienfuegos. The local charter company, Platten Sailing, is the trailblazer, but major international operator Dream Yacht Charter is also present. Havana is served by numerous airlines, with flights also offered to Varadero. However, both airports are approximately three hours away from the charter base. The base in Cienfuegos offers good infrastructure, but it is customary in Cuba to take a local marinero with you, who can serve as a guide and assist with navigation and cartographic coverage.
British Virgin Islands
The British Virgin Islands offer an easy and safe area for sailing in the Caribbean. It provides uninterrupted idyllic tropical views of emerald green islands, deep blue seas, and endless beaches and palm trees. The archipelago consists of over 60 islands located close to each other, with stable borders and well-protected navigation areas from Atlantic waves. Since the last devastating hurricane, these islands have become the center of Caribbean yachting tourism. Sandy Cay is one of the most popular and beautiful spots among the exhibition-like islands.
Swimming in this area is similar to the Mediterranean: short passages, good yacht harbors, and numerous guest buoys in bays. There are also beach bars and restaurants nearby. However, the popularity of the area, high prices, and the density of yachts are drawbacks. Guest buoys often fill up by noon. Nevertheless, this water area is suitable for inexperienced sailors and breathtakingly beautiful. Unfortunately, everything comes with a cost.
Chartering in the British Virgin Islands
Popular charter fleet operators, such as Dream Yacht Charter, Moorings, and Sunsail, are located in Tortola. In general, there are more available beds on yachts than in hotels on the islands, and the number of charter ships is high. There are no direct flights from Europe to the archipelago, but you can fly to Saint Martin and then take a local flight to reach the British Virgin Islands.
Belize
Navigation area
Belize is the only Central American country where English is the official language. It shares borders with Mexico to the north and Guatemala to the south. The country’s coastline boasts the largest continuous coral reef in the Northern Hemisphere, making it one of the best locations for snorkeling and scuba diving in the entire Caribbean.
There are numerous flat islands located between the mainland and the reef. Sometimes these islands are crowded with tourists and full of life, and other times they are secluded and deserted, but they always offer a typical tropical paradise – beautiful beaches, palm trees, and crystal clear waters. Almost the entire coast of Belize is an idyllic paradise, making it a perfect destination for adventurous explorers.
The primary charter area is in the shallow waters within 15 nautical miles between the mainland and the outer reef. This area is strewn with coral reefs and requires a lookout and experience in navigating through areas with underwater obstacles. Sailing mostly consists of visiting islands, where the only available anchorage option is to anchor yourself. However, these islands look like the perfect habitat for Robinson Crusoe, and yachtsmen with a passion for travel and discovery will find heaven on earth in Belize. The charter base in Placencia already offers a wonderful tropical landscape, making it an excellent destination in itself.
Note that most charter operators limit sailing opportunities to the shallow water zone since passages through the reef’s straits into the open ocean are considered too dangerous. However, for experienced high-seas yachtsmen who came on their own yachts, the whole territory is open.
Charter in Belize
The Moorings and Sunsail charter bases are located in Placencia. We highly recommend taking two weeks to explore the large and touristy islands of Cay Cay and Ambergris Cay, which can be reached with a round trip of about 250 nautical miles. The fastest way to get to Belize is by flying to Belize City via the US and then taking a local plane to Placencia.
Leeward Islands
Navigation Area
Eight island nations (St. Martin, St. Martin, St. Barthelemy, Anguilla, St. Kitts and Nevis, Antigua, and Barbuda, Guadeloupe, and Montserrat) stretch over 200 nautical miles, providing an opportunity to experience the diversity of the Caribbean Sea. The former English, Dutch, and French colonies lie side by side like brightly colored cubes. It is hard to find another place in the world where such a significant contrast exists between poor countries like Anguilla or Dominica and well-developed ones like St. Maarten or Guadeloupe.
Although usually favorable weather-wise, this region is hampered by open passages to the Atlantic Ocean and large distances between the islands. Nevertheless, the smooth trade winds make sailing a pleasant and generally not too difficult experience. St. Barts, for example, offers exceptionally interesting options for relaxing on the coast.
Visiting all the islands of the archipelago may not be feasible for a two-week vacation. A classic itinerary for a 14-day trip from St. Maarten includes a round trip with visits to St. Kitts, Antigua, and Barbuda. Alternatively, you can start from Guadeloupe or Antigua and combine these two neighboring islands in one trip. Both islands offer plenty of attractive attractions such as Lonvilliers harbor just north of St. Marthe, while Barbuda and Dominica are within easy sailing reach.
Charter in the Leeward Islands
The island of Saint Martin, which is divided into two states, is the hub of yacht tourism in the Leeward Islands. Almost all international sailing fleet operators have their bases here. Travelers from the Old World can easily start with a direct flight from several European countries, especially from Paris and Amsterdam.
Windward Islands
Navigation Area
The classic Caribbean tour covers four island nations: Martinique, Saint Lucia, Saint Vincent and the Grenadines, and Grenada. The chain of these islands stretches for about 150 nautical miles. Crossings between large islands can take five or six hours. However, for many yachtsmen, these transitions will seem too tiring due to the large Atlantic waves. Meanwhile, the west coast of the islands is usually calmer, and the crossing distances are much shorter, such as when sailing between the numerous small islands of the Grenadines. The reefs of Tobago Island are a must-see.
Most yachtsmen start sailing in the town of Le Marin in the south of Martinique, the center of yachting tourism in the area. The destination of each hike is the small islands of the Grenadines, where you can definitely find the coveted Caribbean idyll. The islands have many good anchorages. This is generally a classic charter route in this area. Along the way, you will come across such gems as the already-mentioned Tobago Reef, Bequia, Mustique, and St. Lucia. The entire voyage will take place in a smooth and constant trade wind. The round trip along this route is approximately 250 nautical miles, enough for a two-week vacation. It is theoretically possible to complete it in a week, but it will be a rushed trip. If you have less time, it makes sense to start sailing to the Grenadines from St. Lucia or Grenada.
Charter in the Windward Islands
Major charter bases in Martinique, such as Dream Yacht Charter, are easily accessible by air via Paris. There is a direct connection to St. Lucia, where there are Sunsail and Moorings bases, from Germany and England. If you want to travel to this area from the south, fly directly to Grenada.
