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Caribbean Hang Out Cruise - St Maarten to Antigua — Sailing Holiday in Sint Maarten & Antigua & Barbuda
Sailing Holiday from Sint Maarten to Nelson's Dockyard — Sint Maarten
Caribbean Hang Out Cruise - St Maarten to Antigua — Anguilla & Sandy Island
Sailing Holiday from Sint Maarten to Nelson's Dockyard — St. Barth
Caribbean Hang Out Cruise - St Maarten to Antigua — Guadeloupe
Sailing Holiday from Sint Maarten to Nelson's Dockyard — Nelson's Dockyard, Antigua
Caribbean Hang Out Cruise - St Maarten to Antigua — Sailing Holiday in Sint Maarten & Antigua & Barbuda
Sailing Holiday from Sint Maarten to Nelson's Dockyard — Sint Maarten
Caribbean Hang Out Cruise - St Maarten to Antigua — Anguilla & Sandy Island
Sailing Holiday from Sint Maarten to Nelson's Dockyard — St. Barth
Caribbean Hang Out Cruise - St Maarten to Antigua — Guadeloupe
Sailing Holiday from Sint Maarten to Nelson's Dockyard — Nelson's Dockyard, Antigua
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Caribbean Hang Out Cruise - St Maarten to Antigua — Sailing Holiday in Sint Maarten & Antigua & Barbuda
Sailing Holiday from Sint Maarten to Nelson's Dockyard — Sint Maarten
Caribbean Hang Out Cruise - St Maarten to Antigua — Anguilla & Sandy Island
Sailing Holiday from Sint Maarten to Nelson's Dockyard — St. Barth
Caribbean Hang Out Cruise - St Maarten to Antigua — Guadeloupe

Mar 19-26

€1,900

6 spaces available

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Caribbean Hang Out Cruise - St Maarten to Antigua

7-night offshore sailing holiday with Southern Ocean Company

CruisingAll LevelsSint Maarten & Antigua & Barbuda - Caribbean

Caribbean Hang Out – Sint Maarten to Antigua Not every sailing trip needs a stopwatch. After the intensity of the Caribbean racing season, this is our chance to slow Eira down and enjoy the islands. We leave Sint Maarten aboard Swan 51 Eira and gradually make our way south towards Antigua, exploring some of the best-known – and some less obvious – places in the northern Leeward Islands along the way. There will be proper sailing. In the Caribbean trade winds a Swan 51 is far too enjoyable to leave under-powered. But there is no racing schedule, no starting gun and no reason to rush past a good anchorage. Think swimming before breakfast, a few hours of sailing, lunch in the cockpit, another island appearing over the horizon and an afternoon ashore when somewhere catches our interest. Possible stops include Anguilla, St Barth, Guadeloupe and the smaller islands and anchorages along the route. Exactly where we go will depend on weather, conditions and what the crew feels like doing. That's intentional. Eira is our home for the week rather than simply transport between hotels. Breakfast and lunch are served aboard and most evenings we'll have the opportunity to go ashore, explore and find somewhere local for dinner. You're welcome to sail actively – helm, trim, navigate and learn the boat – or simply relax and enjoy the journey. This trip is suitable for beginners as well as experienced sailors. Eventually we make our way into English Harbour and Nelson's Dockyard in Antigua, one of the great gathering places of the sailing world and an appropriate place to finish a week aboard a classic Swan. No racing. No ambitious mileage target. No need to turn every day into an expedition. Just a good boat, warm trade winds and enough time to enjoy where they take us.

Up to 8 aboard

Sailing Itinerary from Sint Maarten to Nelson's Dockyard

Why We Love This Sailing Holiday

A gloriously unhurried island hop from Sint Maarten to Antigua on a Swan 51, where the biggest decision most days is swim before or after lunch. Clear water, easy sailing and just enough civilisation to keep things interesting.

1

Departure from Sint Maarten

2

Sailing from Sint Maarten to Anguilla & Sandy Island

Barefoot Perfection A short sail north brings us to Anguilla, an island known for powder-white beaches and impossibly clear water. We anchor off the tiny, postcard-perfect Sandy Island — a crescent of sand set in a ring of turquoise. What to do: – Snorkel straight off the yacht into crystalline shallows – Paddleboard around the cay – Sink into a beach chair with grilled crayfish and a chilled rosé – Long, lazy lunches with your feet in the sand Back onboard, the afternoon is for chillaxing: shaded cockpit reading, a swim ladder dip, perhaps a siesta as the Swan rests gently at anchor. As the sun lowers, we prepare sundowners — aged Caribbean rum, fresh lime, and crushed mint — served as the sky burns gold and coral. Dinner ashore: seared tuna with mango salsa, coconut rice, and grilled plantain. The sea is flat, the stars outrageous.

3

Sailing from Anguilla & Sandy Island to St. Barth

French-Caribbean Chic Next we glide toward glossy Saint Barthélemy, affectionately known as St Barths. The approach into Gustavia is cinematic — red-roofed houses climbing the hills, sleek yachts lining the harbor. This is barefoot elegance at its finest. What to do: – Espresso and flaky croissants at a harbor café – Boutique browsing and French wines in town – Swim at Colombier Beach, accessible by tender – Beach club lounging with chilled rosé and seafood platters The culinary influence turns distinctly French here: oysters on ice, Provençal rosé, lobster thermidor, tarte tropézienne for dessert. Evenings can be spent ashore at a chic waterfront restaurant — or back aboard, where the chef prepares bouillabaisse infused with Caribbean saffron and local reef fish. Sunset ritual: Slightly aged rum, olives, and warm baguette slices as the harbor lights flicker to life.

4

Sailing from St. Barth to Guadeloupe

Spice, Rainforest & Creole Depth We sail south to Guadeloupe, where the landscape grows dramatic and volcanic peaks rise from the sea. The scent of spice markets and tropical forest hangs in the air. Here the pace remains unhurried, but the flavors intensify. What to do: – Visit local markets brimming with nutmeg, vanilla, and cacao – Hike rainforest trails with views over emerald bays – Taste rhum agricole at a traditional distillery – Snorkel vibrant coral gardens Dinner ashore embraces Creole traditions: slow-cooked colombo chicken, grilled mahi-mahi with lime butter, accras (crispy salt cod fritters) served with ti’ punch. Evenings are balmy and musical — perhaps a little zouk drifting across the anchorage.

5

Arrival in Nelson's Dockyard

Nelson's Dockyard, Antigua

A Historic Finale Our final leg carries us to Antigua and Barbuda, finishing in the historic embrace of Nelson’s Dockyard. This UNESCO-listed Georgian naval dockyard is a fittingly elegant conclusion — stone buildings glowing in late-afternoon light, masts rising behind centuries-old brickwork. What to do: – Wander the restored naval quarters and maritime museum – Sip dark rum cocktails at a dockside bar – Swim in secluded coves around English Harbour – Celebrate the final evening with a Caribbean tasting menu For the farewell dinner: grilled Antigua lobster, charred vegetables with thyme, passionfruit pavlova, and a final bottle of Champagne under the cockpit stars.

Meet Your Sailing Operator

Southern Ocean Company
Southern Ocean Company
View Company Profile

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.

Why We Love Southern Ocean Company

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.

Sailing Yachts on This Trip

Your specific vessel is assigned based on your selected dates. All vessels meet our high standards for comfort and safety.

Eira

Eira

Swan - 51

LOA: 51ft (15.62m)

Who Is This Sailing Holiday For?

Do I Need Previous Sailing Experience?

Beginner

No sailing experience required. Perfect for newcomers.

Intermediate

Some sailing experience helpful. Comfortable on the water.

Advanced

Significant sailing experience required. Challenging conditions.

How Much Hands-On Sailing Is Included?

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.

Will I Have Any Duties on Board?

No

All meals and cleaning are taken care of

What Is the Minimum Age?

18

What Is Sailing on This Holiday Like?

This is not a rushed itinerary. It’s a languid progression from anchorage to anchorage. Long swims, late breakfasts, unhurried lunches, sunset cocktails, and evenings scented with sea salt and grilled lobster.

What's Included in Caribbean Hang Out Cruise - St Maarten to Antigua

Included

  • Accommodation Onboard
  • Food Onboard
  • Wet Weather Gear
  • Bedding
  • Breakfast onboard
  • Lunch onboard

Optional Extras

No optional extras

Not Included

  • Eating Out
  • Alcohol Onboard
  • Travel Transfers
  • Flights
  • Sailing Boots
  • Towels
  • Dinner ashore

Why Book with SailTies

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

One date available

From €1,900 EUR per person

Secure your place today from €570 EUR

March 2027

Mar 19-26
Eira
€1,900 (€570 today)
6 spaces available
Book

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.

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