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 adventure takes us through the less-travelled southern Leeward Islands: St Lucia, Martinique, Dominica, Guadeloupe, and Antigua. These islands are the Caribbean at its best: wild, characterful, and full of soul. Rather than polished resorts an big tourist crowds, think jungle-covered peaks, quiet anchorages, hot springs, hidden trails, and warm island culture. This is the side of the Caribbean many never see.
The sailing is superb. With around 30–40 nautical miles between each island, we get a perfect rhythm of daily hops under sail and time ashore to explore. So expect warm trade winds, sun on your back, and steady hands on the helm. From rainforest treks to coral reefs and colourful markets, we reckon this is coastal adventure sailing at its most rewarding.
St Lucia
Our journey starts in St Lucia, where the dramatic Pitons rise steeply from the sea and rainforest-covered hills frame the coastline. It’s the perfect place to settle in, get to know the crew, and begin some light training as we prepare for the voyage ahead. After safety briefings and an introduction to the boat, we cast off for our first short sail north to the beautiful anchorage at Marigot Bay, a calm, palm-fringed inlet and an ideal first stop before we strike out across open water.
Martinique
From St Lucia, we set sail across open water for the first time. It’s around 30 miles north to the rugged coastline of Martinique. It’s a lovely passage, powered by the warm trade winds. On arrival, we step ashore into the island’s striking blend of French sophistication and Caribbean rhythm. Martinique is alive with history, from the ruins of Saint-Pierre, once the “Paris of the Caribbean,” destroyed by the eruption of Mount Pelée, to the colonial charm of Fort-de-France with its forts, libraries, and grand architecture. We may explore colourful markets, sample Creole cuisine, or visit the tropical beauty of Balata Gardens. With its volcanic peaks, sugarcane plantations, and haunting historical layers, the island is rich culture and raw natural beauty and an unforgettable stop on our journey north.
Dominica
From Martinique, we continue our voyage north with a spectacular sail to Dominica, often the wildest and most memorable landfall of the trip. Towering green peaks rise from the sea, and as we approach, the scent of damp rainforest hangs in the air. This is the Caribbean at its most raw and unspoiled. Known as the “Nature Island,” Dominica is laced with rivers, waterfalls, and volcanoes. We usually stop here for a full day and use the time to paddle up the Indian River through tangled mangroves, hike to steaming hot springs in the rainforest, or explore the colourful capital of Roseau, where the island’s Kalinago and colonial heritage meet. With its dramatic terrain, warm-hearted people, and a deep sense of wild isolation, Dominica always feels like stepping into another world.
Guadeloupe
Our next sail takes us to Guadeloupe, a butterfly-shaped archipelago that offers a rich contrast of wild landscapes and laid-back island life. After landfall, we’ll explore anchorages tucked beneath cliffs, wander quiet beaches, and feel the gentle pace that defines this part of the Caribbean. On the mountainous island of Basse-Terre, there are rainforest hikes that lead to the smoking summit of La Soufrière volcano and hidden waterfalls in Guadeloupe National Park. Over on Grande-Terre, life is slower.
Think beachside cafés, colourful markets, and turquoise lagoons. It’s a place to dive off the boat, grab a cold drink ashore, and soak up the rhythm of the islands. From fresh-baked baguettes in sleepy fishing villages to snorkelling in crystal-clear bays, Guadeloupe is where sailing always seems to feel effortlessly joyful.
Antigua
Our final sail takes us into Antigua’s Jolly Harbour, and with it comes the unmistakable feeling of arrival. After days spent navigating windswept channels, anchoring off wild coasts, and exploring jungle-clad islands, this sheltered bay on Antigua’s west coast offers a calm, quiet finish.
There’s no fanfare, just the warm sun on deck and the low murmur of life ashore. Antigua has long been a haven for sailors, and as we tie off our lines in the marina, there’s always a sense after this route that a true adventure has been completed. The crew is confident and friendly and every scuff, bruise and laugh has earned its place. It’s a fitting close to a true Caribbean adventure.
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