The Caribbean is a paradise for sailing enthusiasts, offering countless opportunities to explore beautiful islands, blue waters, and exotic landscapes. If you dream of adventure, week-long or two-week sailing trips are an excellent way to experience the charms of the Caribbean. In this article, we will present you with several attractive routes that will allow you to discover the magic of the Caribbean on longer journeys.

Great Antilles Island Route

A sailing trip through the Great Antilles Islands is an extraordinary adventure. The route typically starts in Jamaica, where you can immerse yourself in the sounds of reggae and enjoy stunning beaches. Then, you can sail to Cuba to discover its rich history and the charm of ancient Havana. The next stop is the Dominican Republic, known for its beautiful Punta Cana beaches and rich culture. The journey concludes in Haiti, where you can explore unspoiled beauty and charming fishing villages.

Lesser Antilles Route

The Lesser Antilles is a group of islands in the eastern Caribbean that offer breathtaking landscapes and cultural diversity. A sailing trip through the Lesser Antilles usually begins in Barbados, where you can enjoy beautiful beaches and magnificent coral reefs. Then, you can visit Grenada, known as the „Spice Island,” where you can discover beautiful bays and lively markets. Other stops include Saint Lucia, Dominica, Antigua, and other charming islands that will captivate you with their nature and culture.

Turquoise Islands Route

The Turquoise Islands are a group of islands in the northwest Caribbean renowned for their beautiful waters and excellent diving spots. A sailing trip through these islands typically starts in the Turks and Caicos Islands, where you can explore pristine beaches and extraordinary coral reefs. Then, you can sail to the Bahamas, which offer a wide range of attractions, from luxurious resorts to picturesque fishing villages. Other possible stops include the Cayman Islands, Jamaica, and other islands where you can enjoy the blue waters and relax on beautiful beaches.

San Blas Archipelago Route

The San Blas Archipelago is a group of over 300 islands off the coast of Panama, home to the indigenous Kuna people. Sailing through this archipelago is a unique experience that allows you to discover the unspoiled charm and traditions of this region. You can enjoy swimming in crystal-clear waters, diving among coral reefs, and learning about Kuna culture. Each island has its unique attractions and charms, making this route an unforgettable adventure.

Cape Verde Islands Route

The Cape Verde Islands are a group of islands off the west coast of Africa that offer spectacular landscapes and excellent sailing conditions. A sailing trip through these islands usually starts in Cape Verde itself, where you can explore beautiful beaches, volcanic rock formations, and picturesque fishing villages. Then, you can visit São Vicente, Santo Antão, Sal, and other charming islands that will provide you with unforgettable views and experiences.


Traveling through the Caribbean on week-long and two-week sailing trips is an excellent way to discover the beauty of this region. Routes through the Great Antilles Islands, Lesser Antilles, Turquoise Islands, San Blas Archipelago, and Cape Verde Islands offer extraordinary landscapes, cultural diversity, and unforgettable adventures. Choose the route that interests you the most and embark on an unforgettable journey through the Caribbean.

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