Caribbean Hang Out Cruise - St Maarten to Antigua
A 9-Day Sailing Escape Through the Northern Leewards Slow down. Sail deep. Taste everything. Step aboard a classic Swan 51 and let the trade winds carry you on a relaxed nine-day voyage through the luminous waters of the northern Caribbean. Our journey begins in Sint Maarten, departing from elegant Simpson Bay — a natural lagoon where superyachts sway gently against a backdrop of green hills and pastel waterfront cafés. After a welcome Champagne toast on deck, the sails rise. The rhythm shifts. You’re on island time now.
Why We Love This Trip
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.
Meet the Operator
Southern Ocean Company and Swan 51 “Eira" Southern Ocean Company was founded in the first years of the new century but basically restarted in 2009 when shares got redivided among a new set of owners. The mission was to purchase a yacht capable of doing long transatlantic voyages, housing large crews and put it out “on the trade". After considering a number of options the decision fell in favour of a proven design, the Swan 51, and the optimal version, the alternative one layout with its additional crew space. The search started immediately. After viewing several potential boats one stuck out, the hull 009 for sale in Sweden. She had previously done several seasons in the Caribbean and was already equipped for long hauls. Her general condition was also good, or as the surveyor from Nautor loosely put it – “she’s pretty much the same boat that rolled out of the factory in 1981”.
Why We Love Swan Eira
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.
Trip Itinerary
Start - Sint Maarten
Day 2 - 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.
Day 3 - 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.
Day 4 - 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.
End - 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.
Is This Trip For Me?
What experience level is required?
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 sailing participation will there be?
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 there be any domestic duties?
No
All meals and cleaning are taken care of
Minimum Age
18
What will the type of sailing be 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.
Vessels on This Trip
Your specific vessel is assigned based on your selected dates. All vessels meet our high standards for comfort and safety.
Eira
Swan - 51
LOA: 51ft (15.62m)
What's Included
Included
- Accommodation Onboard
- Food Onboard
- Wet Weather Gear
Optional Extras
No optional extras
Not Included
- Eating Out
- Alcohol Onboard
- Travel Transfers
- Flights
- Sailing Boots
- Bedding
- Towels
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 £1,680 GBP per person
Prices shown in USD are approximate conversions, using today's conversion rate. This trip is priced by the operator in GBP and payment will be taken in GBP.