1/19
Feb 1-7
€1,680
5 spaces available
Feb 1-7
€1,680
5 spaces available
6-night sailing holiday with Southern Ocean Company
Windward–Leeward Cruise – St Lucia to Antigua There are few better ways to experience the Caribbean than sailing north through the islands with the trade winds behind you. We start in Rodney Bay, St Lucia, and finish in one of the great historic sailing destinations of the Caribbean: Nelson's Dockyard in Antigua. Between them lie Martinique, Dominica, Îles des Saintes and Guadeloupe – a wonderful mixture of proper sailing passages, spectacular scenery, French-Caribbean culture and some very good places to drop the anchor. Our yacht for the journey is Swan 51 Eira, a German Frers-designed Nautor Swan built for exactly this sort of sailing. She is powerful enough to make the passages interesting, comfortable enough to live aboard and small enough for everyone who wants to sail to become genuinely involved. This isn't a fixed-itinerary package holiday. We have a route and destinations in mind, but we're sailing a yacht, so weather and conditions always have a say. If we discover somewhere worth staying another evening, we can. If the forecast tells us to move, we move. Expect some exhilarating trade-wind sailing between the islands. The passages are long enough to experience Eira properly under sail, but most evenings should find us at anchor or ashore somewhere new. You are welcome to participate as much as you like. Take the helm, trim sails, navigate and learn more about sailing a Swan – or simply enjoy being on the water. No previous sailing experience is necessary for this cruise. Breakfast and lunch are normally enjoyed aboard, while evenings give us the opportunity to explore the local restaurants and villages ashore. The Caribbean changes remarkably as you move north. St Lucia's dramatic mountains give way to Martinique's French influence, wild Dominica, tiny Îles des Saintes, Guadeloupe and finally Antigua's extraordinary sailing culture. Eight days, several countries, one classic Swan and some of the finest sailing waters in the world. This is not about seeing the Caribbean from a resort. It's about sailing through it.
Why We Love This Sailing Holiday
A proper island-hopping passage from St Lucia to Antigua on a Swan 51, ticking off some of the Caribbean’s best sailing along the way. Trade winds, great stops and a finish in Nelson’s Dockyard that feels like arriving exactly where you’re meant to.
Rodney Bay, St. Lucia
Day 1 - 2 We clear Rodney Bay and set a northerly course toward Martinique. Expect a spirited beam reach across turquoise waters. Martinique blends French sophistication with Caribbean rhythm—charming anchorages, world-class boulangeries, and lush volcanic landscapes. Evenings are spent beneath dramatic green hills.
Day 3 - 4. Next we sail toward the untamed beauty of Dominica, often called “The Nature Island.” Towering mountains plunge into the sea, waterfalls cascade through rainforest valleys, and the scent of spice hangs in the air. This is raw Caribbean—authentic, dramatic, unforgettable. The fortunate can get a glimpse of the rare sperm whale pod cruising these exceptional waters.
Day 5. A shorter but spectacular passage takes us to the idyllic archipelago of Îles des Saintes. French-Caribbean charm defines this stop: pastel houses, quiet anchorages, and panoramic views from hilltop forts. Swim in crystalline bays or wander cobbled streets with a café in hand.
Day 6 - 7. We continue to Guadeloupe, a butterfly-shaped island rich in Creole culture and dramatic scenery. Explore vibrant markets, hike through tropical forests, or relax on secluded beaches. Under sail, the Swan 51 comes alive in the steady trade winds.
Nelson's Dockyard, Antigua
Day 8 - 9. Our final offshore leg brings us to Antigua and Barbuda, famed for its sailing heritage. We conclude in historic Nelson’s Dockyard, a beautifully restored Georgian naval base and UNESCO World Heritage Site. Mooring here feels like arriving at the spiritual home of Caribbean yachting. A final evening toast marks the completion of a remarkable island-hopping passage through some of the Caribbean’s most storied waters.
Southern Ocean Company Southern Ocean Company has been taking people sailing, racing and across oceans since 2009. Our idea has always been simple: offer genuine sailing experiences on proper yachts, with small crews, active participation and the freedom to enjoy sailing for what it really is. We are not a conventional charter company or sailing school. Our programme ranges from offshore races and international regattas to ocean crossings and relaxed cruising in some of Europe's most beautiful sailing areas. Depending on the adventure, we sail aboard our Swan 51 Eira or our Bavaria 50, choosing the yacht that best suits the character of the trip. At the heart of our offshore and racing programme is Eira, a German Frers-designed Nautor Swan 51. Built in Finland and designed for serious offshore sailing, she combines the craftsmanship and character of a classic Swan with the performance, strength and seaworthiness for which these yachts have become known around the world. Eira has been part of Southern Ocean Company since 2009 and has accumulated an extensive sailing history ranging from ocean crossings to some of Europe's and the Caribbean's best-known regattas. Rather than moving her from event to event by other means, we sail her whenever practical. The passages, changing coastlines and people joining along the way are as much a part of her story as the races themselves. Our cruising programme has a different rhythm. Aboard our Bavaria 50, including our Finnish Archipelago adventures, the emphasis is on discovering places that are best experienced from the water. With a small number of guests, we can remain flexible, explore islands and anchorages away from the usual routes and let weather, curiosity and the crew help shape the journey. Whatever the yacht or destination, life aboard is hands-on. Guests are welcome to helm, trim sails, navigate and take part in the everyday running of the boat. On an ocean passage this can mean watchkeeping, night sailing and learning to live as a crew far from land. During a regatta the focus shifts towards teamwork, boat handling and getting the best possible performance from the yacht. On a summer cruise it may simply mean taking the helm for a few hours before finding a quiet anchorage for the evening. You don't need to be an expert sailor to join many of our adventures. What matters more is curiosity, a willingness to participate and an understanding that sailing is a shared experience. For our more demanding offshore races and ocean passages, previous experience may be required. We deliberately keep the atmosphere informal. Seamanship and safety are taken seriously, and when we race, we race to do well. But sailing is also about the people you meet, dinners after a long day at sea, quiet anchorages, conversations during night watches and the friendships that have a habit of developing when a small group shares a boat. Some people join us for their first real sailing adventure. Others come to race, build offshore miles or cross an ocean. Many return for another chapter. We're going somewhere. Come aboard for part of the journey.
Seb and his Swan 51, Eira, have been part of the charter racing scene since 2009. On board you’ll find the right balance of competitive racing and a friendly, welcoming crew. Between regattas, Eira runs some excellent sailing itineraries as she moves between race venues.
Your specific vessel is assigned based on your selected dates. All vessels meet our high standards for comfort and safety.
Swan - 51
LOA: 51ft (15.62m)
Beginner
No sailing experience required. Perfect for newcomers.
Intermediate
Some sailing experience helpful. Comfortable on the water.
Advanced
Significant sailing experience required. Challenging conditions.
Active Crew Member
Full participation in all sailing activities.
Optional Involvement
Participate as much or as little as you like.
Passenger
Sit back and enjoy the ride.
No
All meals and cleaning are taken care of
18
Set sail on a true bluewater legend and discover the Caribbean the way it was meant to be experienced — under canvas, horizon wide open, and island lights twinkling at anchor.
No optional extras
Tried and tested sailing experiences, from our pick of the world's best operators
EXPERT-LED SAILING ADVENTURES
All our trips are led by qualified skippers and sailing instructors
TRIED & TRUSTED
We only work with the most reputable sailing operators and yacht providers
SOLO & GROUP-FRIENDLY SAILING
Perfect for solo sailors looking to join a crew or groups wanting to charter
WORLD-CLASS CUSTOMER SUPPORT
Our team is on-hand 24/7 to help you before, during and after your adventure
From €1,680 EUR per person
Secure your place today from €504 EUR
Prices shown in USD are approximate conversions, using today's conversion rate. This trip is priced by the operator in EUR and payment will be taken in EUR.