Sailing holidays in the Caribbean

The Caribbean islands are among the most popular sailing areas in the world. The Caribbean Sea, the 7,000 islands, islets and cays populating its waters and the surrounding coasts of North, Central and South America have a lot to offer to sailors, from excellent sailing conditions and warm weather year-round to an enormous variety of lush tropical landscapes, clear blue waters, spectacular coral reefs and rich underwater life. Also known as the West Indies, the islands include a great number of the world's top yacht charter destinations, some of which are ideal for Caribbean island hopping cruises and provide travellers with countless natural treasures and many unique cultures to explore.

  • Rent a yacht and sail to Aruba to relax on the island’s beautiful beaches and explore the spectacular views from the California Lighthouse, Haystack Mountain and Casibari Rock and Ayo Rock Formations
  • Visit the diving sites of Grenada to discover the island’s coral reefs, rich marine life, an Underwater Sculpture Park and the region’s largest sunken ship
  • Enjoy the sounds of Junkanoo, Calypso and Soca in the Bahamas and discover the archipelago’s amazing birds, rocky raccoons, dolphins, angelfish and coral reefs
  • Swim, snorkel and dive on the beaches of Barbados, try the flying fish and coo-coo and taste the delicious local rum drinks before exploring the island’s vibrant nightlife
  • Explore the coral reefs of the Cayman Islands, visit the Cayman turtles on Boatswain's Beach, and pet friendly stingrays in Stingray City in the waters of Grand Cayman


Weather conditions/When to go

The Caribbean region has a tropical climate and the weather is warm throughout the year. Warm trade winds blow almost constantly from the east and occasional northwestern winds are felt around the northern islands in the winter. Winters are nevertheless warm, but somewhat drier than the summers. The winds are the strongest in December and January and considerably weaker from June to November.

The wet season in the Caribbean has a higher risk of hurricanes, which usually strike northwest of Barbados and north of Grenada. The hurricane season lasts from June to November, while the dry season, between December and May, has less rainfall, with only occasional, short-lived showers to be expected from time to time. Those setting sail to the Caribbean during the wet season must always keep their eye on the weather forecast, as the hurricane prediction systems will usually give them a warning period of 2-3 days.   

The best time to go to the Caribbean is from March to June, when the weather is more settled, the tropical fruit is in season, and there are fewer tourists around. August and September are best avoided because of increased incidence of hurricanes.  The most popular season for boat charters is around Christmas, when the prices are highest, the marinas full, and the Christmas winds quite strong.

The weather patterns are different for each island and depend mainly on the island’s topography. The flatter islands such as Anguilla or Antigua typically have less rainfall, while the more mountainous ones, including St. Vincent and Dominica, are covered with rainforest and have regular rain showers over the higher areas.


Caribbean regions and marinas

The massive Caribbean archipelago forms an island chain 4,020 kilometres long and up to 257 kilometres wide, and includes 13 sovereign states and 17 dependent territories. It is divided into several regions: the Lucayan Archipelago, the Greater Antilles, the Lesser Antilles and the Leeward Antilles (ABC Islands). Each of these regions contains scenic archipelagos and islands with relatively short sailing distances that make wonderful destinations for a Caribbean island hopping cruise.

Anchorages in the Caribbean are mostly shallow and secure, and typically found on the western side of the islands, where the easterly trade winds help boats to the shore.

The Lucayan Archipelago comprises the Bahamas and the Turks and Caicos Islands, while the Greater Antilles grouping consists of several larger Caribbean islands: Cuba, Hispaniola (comprising Haiti and the Dominican Republic), Jamaica, Puerto Rico and the Cayman Islands. 

The Lesser Antilles region comprises a long arc of smaller islands extending from the Virgin Islands to Grenada, and is divided into two subgroups: the Leeward Islands and the Windward Islands. The Leeward Islands include Anguilla, Antigua and Barbuda, Saint Martin, Saba, Sint Eustatius, Saint Barthélemy, Saint Kitts and Nevis, Montserrat and Guadeloupe. The Windward Islands are Dominica, Martinique, Saint Lucia, Saint Vincent and the Grenadines, Grenada, Barbados, and Trinidad and Tobago.

The Leeward Antilles include Aruba, Bonaire and Curaçao, also known as the ABC Islands, and a number of islands located to the east of these three, including the Los Monjes Archipelago, La Tortuga, La Sola, Los Testigos Islands, the Los Roque Archipelago, Los Hermanos Archipelago and Las Aves Archipelago.


Things to do in the Caribbean

The Caribbean islands offer an enormous variety of options for family and group sailing holidays, as well as for adventure cruises and romantic getaways.  Most islands have spectacular beaches that are ideal for swimming, snorkelling and other beach activities and, regardless of the specific destination, travellers will have a relaxing holiday with lots of amazing tropical scenery and great weather to enjoy.

The main sailing destinations in the Lucayan Archipelago are the Bahamas and the Turks and Caicos Islands. With 700 islands and 2,000 cays to choose from, the Bahamas attract more than 5 million visitors each year, more than 70% of whom are cruise visitors. Known for its natural beauty, unique culture and music, the archipelago offers plenty of opportunities to explore the colourful tropical aquatic life, coral reefs, and countless bird species, as well as to enjoy the rhythms of the region's distinctive musical styles.

The Turks and Caicos are one of the most popular beach destinations in the Caribbean. Only 60 km long, the archipelago is ideal for island hopping holidays as its 40 islands and cays offer plenty of sunshine and breezy winds throughout the year. 

The Greater Antilles region also offers plenty to see and enjoy. The larger islands – Cuba, Jamaica, Hispaniola (Haiti and the Dominical Republic) and Puerto Rico – are by far the most visited ones, while the Cayman Islands are a popular diving destination, known for their outstanding coral reefs and exceptionally clear waters.   

The Lesser Antilles are home to some of the best-known tourist destinations in the Caribbean. The Leeward Islands, which are less exposed to the region's trade winds, and the Windward Islands, which stand in the way of the trade winds from the east, are a colourful blend of cultures and landscapes and include some of the world's smallest independent nations. Anguilla is known for its white sand beaches and gorgeous bays, as well as for the many turtles that nest there. Antigua and Barbuda, another popular beach destination, are home to Nelson's Dockyard and several old British forts, as well as to Mount Obama, the islands' highest point and a national park named after the former U.S. President.

With more than 60 volcanic and coral islands and cays, the British Virgin Islands make an excellent destination for an island hopping tour. The coral reefs, pristine beaches, scenic villages and historic shipwrecks are some of the archipelago's main draws. The U.S. Virgin Islands are home to the Buck Island Reef National Monument and one of the best marine gardens in the Caribbean, some of the region’s largest mango forests, a submarine canyon, and the Virgin Islands National Park, preserving remains of civilizations dating back to 1100.

The Guadeloupe islands attract countless visitors to the beaches of the island of Grande Terre, the lush landscapes and waterfalls of Basse Terre, and the archipelago’s nature parks and volcanos, rum distilleries and diving schools.

Saint Kitts and Nevis, a pair of volcanic islands separated by a narrow channel, are known for their scenic beauty, popular festivities, diving sites and remnants of the colonial-era culture. The Brimstone Hill Fortress, a UNESCO Heritage Site and national park, offers amazing views of the surrounding area and islands.

The rocky shores of the volcanic island of Saba, known as the Unspoiled Queen, are a haven for nature lovers, while Saint-Barthélemy draws a number of celebrities each year and is a popular destination for beach weddings. Beaches are also the main draw of Saint Martin, known for the buzzing nightlife and casinos on the Dutch side of the island. 

Barbados, the Little Britain of the Caribbean, is home to numerous luxury resorts on its west coast and harbours several scenic historic sites and a lovely Botanical Garden in the interior. Soup Bowl on the east coast is a popular destination for watersports, while Silver Sands on the south coast is a hotspot for windsurfing. The coral reefs and shipwrecks around the island offer some of the best scuba diving experiences in the Caribbean. 

Dominica, also known as the Nature Island of the Caribbean, has some of the region’s most spectacular and diverse flora and fauna. The island’s rugged mountains, volcanic peaks, waterfalls, the large, thermally active Boiling Lake in the UNESCO-protected Morne Trois Pitons National Park, and a snorkelling spot known as Champagne for the streams of bubbles emitted by underwater volcanic vents, are some of the island’s best known attractions. 

Martinique appeals to nature lovers, beach goers and foodies alike as the island’s rain forests, scenic canyon, beautiful beaches and French and Creole cuisine offer an unparalleled experience on a Caribbean cruise.   

Saint Vincent and the Grenadines, a popular destination for island hopping cruises, have a rugged, volcanic landscape and harbour several nature parks with spectacular views of the surrounding area.

Grenada, the region’s spice capital and another popular destination for weddings, consists of several islands, including the larger Grenada, Carriacou and Petite Martinique. The islands offer plenty to see, from spice and floral gardens to historic forts, waterfalls and lakes. They are home to the world’s first Underwater Sculpture Park and the largest shipwreck in the Caribbean. 

Trinidad and Tobago, one of the world’s most prosperous tiny island nations, consists mainly of two islands traversed by scenic mountain ranges, hills, peaks, rivers and streams. The islands are highly industrialized, but nonetheless, offer a number of sites for nature lovers. These include the Caroni Bird Sanctuary, La Brea Pitch Lake, a tropical rainforest reserve, and Down the Islands, a group of picturesque islands between Trinidad and the coast of Venezuela. 

The Leeward Antilles comprise the ABC Islands, all part of the Kingdom of the Netherlands, and a number of islands and archipelagos that are Federal Dependencies of Venezuela. Aruba, the “A” in ABC, is known for its flat terrain, warm waters and lovely white sand beaches. The island harbours a number of natural attractions, including scenic lava and rock formations, Guadirkiri Caves, a butterfly farm, bird sanctuary, donkey sanctuary and ostrich farm. The island is a popular destination for safaris, scuba diving, kayaking, windsurfing, hiking and cycling.

Curaçao, a showcase of the pastel-coloured Dutch architecture, harbours the UNESCO-protected natural harbour of Willemstad, the dive sites around Watamulu, an impressive natural site with an array of hollow rocks and coral reefs, and several marine and national parks with turtle breeding grounds, waterfalls, cave paintings and stunning stalactite and stalagmite formations.

Considerably quieter than its neighbours, Bonaire is a hotspot for diving, cave exploring, wind surfing and bird watching. The island’s lush coral reefs, flamingos, sea turtles, mangrove forests and the dramatic landscape of the Washington Slagbaai National Park provide a refuge for anyone looking for a relaxing holiday in a remote scenic location with plenty of opportunities to try a varied range of delicious traditional dishes.