This adventure is genuine: a Rubicon 3 sailing vacation in the Leeward Islands has no set itinerary. The skipper, mate and you, the crew, will look at the wind and the weather at the time and make a plan for your time on board – and that plan will likely change a few times during the expedition! You may discover a fantastic place and want to spend an extra day exploring, or the wind is from the wrong direction, so you sail somewhere off the initial plan. Making the adventure up as we go is all part of the magic of these trips in the West Indies.
Where are the Leeward Islands
The Leeward Islands are a group of islands in the Lesser Antilles chain of the Caribbean Sea. They are located southeast of Puerto Rico and north of the Windward Islands, separated by the Dominica Channel. These unspoilt, tropical islands are among the most captivating and picturesque in the Caribbean and the ideal destination for a mix of holiday and adventure. To the north, you have the US Virgin Islands and BVIs, St Kitts and Nevis, Sint Martin /St Martin/St Maarten, and St Barts.
Our route explores the southern islands, including St Lucia, Martinique, Dominica, Guadeloupe and Antigua. These are a little more off the beaten track, and gems like Dominica are ones you will never get to see on an average yacht charter.
This stretch of the Leeward Island chain is purely coastal sailing, with around 40 miles between each island being the furthest distance we have to make. It means we will stop and discover somewhere new daily, including fascinating towns and communities, spectacular scenery rich in jungle, volcanoes, coral reefs, quiet anchorages and perfect white sand beaches.
Allied to the trade winds, the sun and warm Caribbean sea make this a magical location for an adventure on a sailing yacht!
St Lucia
This beautiful island is celebrated for its dramatic Pitons and rainforests, including the renowned Edmund Forest Reserve and the captivating Diamond Falls Botanical Gardens. The island has a storied past marked by Franco-British rivalry, now reflected in the colonial charm of Castries and the historical richness of Pigeon Island National Park. Sulphur Springs Park is a one-of-a-kind drive-in volcano we must try if we can.
Martinique
Martinique, 30 miles north of St Lucia, is steeped in history and natural beauty. The island was first settled by the Arawaks, followed by the Caribs, and was discovered by Columbus in 1502. It became a French colony in 1635, and its history is deeply intertwined with the sugar trade and the era of slavery, leaving a significant cultural impact. We can explore the haunting ruins of Saint-Pierre, once known as the “Paris of the Caribbean,” destroyed by the 1902 eruption of Mount Pelée. The island’s capital, Fort-de-France, features historic sites like Fort Saint-Louis and the Schoelcher Library. The Balata Gardens and Les Salines beach offer stunning natural escapes, while the Château Dubuc ruins echo the island’s colonial past. Martinique is an island full of natural wonders, colonial history, and vibrant Creole culture.
Dominica
Dominica, known as the “Nature Island” of the Caribbean, is a tropical paradise with a world-famous coral reef. The island’s rainforests, home to the Morne Trois Pitons National Park, a UNESCO World Heritage site, offer incredible hiking trails leading to the Boiling Lake and Trafalgar Falls. It has nine volcanoes, including Morne Trois Pitons and Morne Diablotins, although all of these are currently considered dormant volcanoes. The history of this Caribbean Island is marked by indigenous Kalinago people and later European colonization, which is reflected in its culture and seen clearly in the historic capital, Roseau. The island’s volcanic terrain also creates many natural hot springs, like those in Wotten Waven, where you can swim and rest under a lush green palm tree.
Guadeloupe
Guadeloupe is an archipelago of islands, perfect for nature lovers with its relaxed atmosphere and mesmerizing blend of natural beauty and rich history. The two islands of Basse-Terre and Grande-Terre offer quite diverse experiences. The small island of Basse-Terre is home to the Guadeloupe National Park, featuring the La Soufrière volcano and the Carbet Falls. Grande-Terre has beautiful secluded beaches like Plage de la Caravelle and charming towns like Sainte-Anne. Guadeloupe’s history, influenced by the Caribs and its colonization by France, is most evident in its Creole culture. The Memorial ACTe museum in Pointe-à-Pitre offers profound insights into the region’s past, particularly the history of slavery. With its captivating mix of natural wonders, colonial heritage, and lively Creole traditions, Guadeloupe is a beautiful place to discover.
Antigua
Antigua, a jewel in the Eastern Caribbean, has 365 beaches, one for each day of the year, with favorites like Dickenson Bay and Half Moon Bay offering crystal-clear waters and perfect white sands. The island’s rich history is highlighted in Nelson’s Dockyard in English Harbour, a beautifully restored naval dockyard and UNESCO World Heritage site, reflecting its importance during colonial times. Antigua’s capital, St. John’s, is home to the baroque St. John’s Cathedral and vibrant local markets. Shirley Heights offers a spectacular lookout point for panoramic views and is well known to all sailors.
The Sailing Season in the Leeward Islands
The season for sailing yachts in the Leeward Islands runs from January through to April. The dates for this year can be found in our Dates & Prices tab. We usually arrive in this region in mid-December, having sailed the Atlantic Ocean in the ARC. The best time to sail and explore these islands is January to April, with steady trade winds and no risk of hurricanes (which come through June to November).
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