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.
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 and big tourist crowds, think jungle-covered peaks, quiet anchorages, hot springs, hidden trails, and island culture. This is a side of the Caribbean many never see.
The sailing is also 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 a new destination most days. From rainforest treks to coral reefs and colourful markets, we reckon this is coastal adventure sailing in the Caribbean at its most rewarding. Here are some of the highlights.
St Lucia: A Standout in the Leeward Islands
St Lucia is one of the most striking islands in the chain, with its steep hills, volcanic peaks, and deep, natural anchorages. The iconic Pitons dominate the skyline, with their sharp green spires rising straight from the water and providing a dramatic landfall. Marigot Bay is picture-perfect, a calm inlet fringed with palm trees and old wooden jetties. It’s a favourite for a quiet night at anchor and a relaxed meal ashore. Further south, the fishing village of Soufrière gives a more local feel, with laid-back streets, hot springs, and sulphur pools nearby.
Martinique
Martinique brings a touch of France to the Caribbean, with quiet charm, fine food, and a coastline made for exploring under sail. The beaches are golden, the sea warm and clear, and every anchorage feels like a new discovery. Sainte-Anne, on the southern tip, is a favourite of ours, with its swaying palms, calm water, and evenings that drift by with the scent of Creole cooking from the shore. Further along the coast, Anse d’Arlet offers another very calm anchorage, perfect snorkelling, and a sleepy charm. Sailing up the west coast, the landscape becomes more dramatic, until we get to Saint-Pierre, once the “Paris of the Caribbean,” sitting in the shadow of a volcano.
Dominica: The Wild Soul of the Leeward Islands
Dominica is 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 fills 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
Shaped like a butterfly and full of contrasts, Guadeloupe offers everything you dream of in a Caribbean landfall. The western wing, Basse-Terre, is mountainous and rainforested, with clouds often clinging to the peaks and waterfalls pouring down to the sea. The eastern wing, Grande-Terre, is gentler, dotted with white-sand beaches, fishing villages, and pastel-painted towns. Sailing the coast, the highlights come thick and fast. The Îles des Saintes, just to the south, are a near-perfect stop, with turquoise anchorages, quiet streets, and we reckon some of the best pastries and coffee you’ll find in the Caribbean. Terre-de-Haut, in particular, is a favourite of ours for its French-Caribbean charm and easy pace. On the main island, Deshaies is a great anchorage backed by green jungle covered hills and small shore side restaurants serving fish straight off the boats. Bougainvillea, in shades of pink, magenta, orange, and purple, spills from every wall and balcony, adding amazing colour to every scene.
Antigua
Antigua is pure sailing heritage. It famously has 365 beaches, one for every day of the year, and a coastline that has deep, welcoming harbours. English Harbour is the beating heart, steeped in maritime history. Nelson’s Dockyard, with its old stone buildings and Georgian charm, is still full of life, with cruisers, racers and superyachts all side by side. Further afield, anchorages like Green Island and Nonsuch Bay sre perfect for peaceful nights under the stars. Inland, the hills roll into the distance, dotted with old sugar mills and villages. Many of us sailors have spent whole seasons based in Antigua and love it. You’ll see why.
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