Sail, Explore and Soak Up the Sun on Idyllic Islands
Sailing in the Caribbean offers a world of adventure across its many islands, from the Windward Islands of Antigua, Dominica, and Guadeloupe to the spice-scented air of the Grenadines.
The Caribbean Sea, with its reliable and warm trade winds, crystal clear waters, and sheltered anchorages, is a sailor’s paradise. It is ideal for novice sailors eager to improve their sailing skills and explore the serene beauty of magical locations such as Dominica or the Tobago Cays. It is also loved by more experienced sailors for its great wind, wide variety, and endless opportunities to explore.
35 Items
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Offshore
Sail the Atlantic in the ARC
31 Days from £5,999
Sail across the Atlantic Ocean with Rubicon 3 in the Atlantic Rally for Cruisers (ARC), a 2800-mile voyage from the Canary Islands to the Caribbean. Four weeks full of adventure, training, exhilarating sailing and memories of a lifetime.
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Join Waitlist
Wednesday 19th November 2025 - Friday 19th December 2025 -
Experience: Low to some
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Region: Caribbean & The Americas
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Caribbean Christmas & New Year Sailing: The Grenadines
12 Days from £2,499
Celebrate Christmas and New Year sailing the Grenadines. Join a hands-on adventure from St Lucia, exploring Bequia, Canouan, the Tobago Cays, Union Island and more. Swim with turtles, wander colourful island markets, and anchor beneath leaning coconut palms. Spend Christmas in tropical calm, then ring in the New Year anchored beneath Caribbean stars. No experience needed. Solo travellers welcome. A unique way to escape winter and welcome the New Year on warm trade winds and open sea.
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Available
Tuesday 23rd December 2025 - Saturday 3rd January 2026 -
Experience: None
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Coastal
The Windwards Islands: Exploring the Grenadines
10 Days from £2,399
Sail the Windward Islands on a hands-on Caribbean sailing adventure. Starting in St Lucia, we island-hop south through the Grenadines, navigating crystal-clear waters, coral reefs, and secluded anchorages. Explore Bequia’s boatbuilding heritage, snorkel with turtles in the Tobago Cays, wander Union Island’s colourful markets, and anchor beneath leaning coconut palms in Salt Whistle Bay. Short distances and plenty of time ashore mean a new destination to explore each day, combining relaxed sailing with real discovery.
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Available
Tuesday 6th January 2026 - Thursday 15 January 2026 -
Experience: None
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Region: Caribbean & The Americas
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Coastal
The Windwards Islands: Exploring the Grenadines
10 Days from £2,399
Sail the Windward Islands on a hands-on Caribbean sailing adventure. Starting in St Lucia, we island-hop south through the Grenadines, navigating crystal-clear waters, coral reefs, and secluded anchorages. Explore Bequia’s boatbuilding heritage, snorkel with turtles in the Tobago Cays, wander Union Island’s colourful markets, and anchor beneath leaning coconut palms in Salt Whistle Bay. Short distances and plenty of time ashore mean a new destination to explore each day, combining relaxed sailing with real discovery.
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Available
January 20-29 2026 -
Experience: None
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Region: Caribbean & The Americas
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Coastal
Grenada Sailing Week
10 Days from £2,199
Grenada Sailing Week is racing without the bluster. Set deep in the southern Caribbean, between the islands of Grenada and Carriacou, it’s low-pressure, high-fun sailing at its best. Expect white sand beaches, jungle-covered hills, turquoise water, and a welcoming crowd. Each day ends with a party or beach BBQ, and the atmosphere is pure Caribbean charm. This is one of our most loved events—and easily the friendliest regatta out there.
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2 Places Available
Friday 23rd January 2026 - Sunday 1st February 2026 -
Experience: None
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Region: Caribbean & The Americas
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Coastal
The Leewards: Emerald Islands Of The Caribbean
10 Days from £2,299
Sail through the Leeward Islands and explore the best of the Caribbean. Begin in St Lucia, anchoring beneath its towering volcanic peaks. In Martinique, soak up the island’s unique blend of French sophistication and Caribbean soul. Head to Dominica to paddle the winding Indian River and hike into thick rainforest. Sail on to Guadeloupe, with its mix of blissful anchorages, white sand beaches, and sleepy offshore islands. Conclude your journey in the sailing mecca of Antigua.
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Available
Wednesday 4th February 2026 - Friday 13th February 2026 -
Experience: None
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Region: Caribbean & The Americas
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Coastal
The Mystery Islands of the Caribbean
10 Days from £2,399
Sail to places most travellers never see: Montserrat, Saba, Statia, Nevis, and Barbuda. Raw, beautiful islands, rich in history, character, and natural wonder. Volcanoes rise from the sea, pink-sand beaches stretch on with barely a footprint, and quiet anchorages offer solitude in these islands that most tourists never reach. From the buried city of Plymouth to the cloud forests of Saba and the wild shores of Barbuda, every island has its own story.
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Available
Tuesday 17th February 2026 - Thursday 26th February -
Experience: None
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Region: Caribbean & The Americas
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Offshore
RORC Caribbean 600
10 Days from £2,499
Race in the RORC Caribbean 600: Six hundred miles of exhilarating offshore racing, weaving through Caribbean islands.
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Join Waitlist
Thursday 19th February 2026 - Saturday 28th February 2026 -
Experience: Low to some
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Region: Caribbean & The Americas
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Coastal
St Maarten Regatta
11 Days from £2,499
Join this exhilarating, week-long regatta, mixing none-too-serious but competitive yacht racing with wonderful Caribbean culture and events ashore.
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Available
Tuesday 3rd March 2026 - Friday 13th March 2026 -
Experience: None
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Region: Caribbean & The Americas
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Coastal
The Leewards: Emerald Islands Of The Caribbean
10 Days from £2,299
Sail through the Leeward Islands and explore the best of the Caribbean. Begin in St Lucia, anchoring beneath its towering volcanic peaks. In Martinique, soak up the island’s unique blend of French sophistication and Caribbean soul. Head to Dominica to paddle the winding Indian River and hike into thick rainforest. Sail on to Guadeloupe, with its mix of blissful anchorages, white sand beaches, and sleepy offshore islands. Conclude your journey in the sailing mecca of Antigua.
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Available
March 03-12 2026 -
Experience: None
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Region: Caribbean & The Americas
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Offshore
Caribbean Offshore 1000: St Lucia to Dominican Republic
12 Days from £2,399
Sail from St Lucia to the Dominican Republic on a 650nm trade-wind passage that blends fast, downwind offshore sailing with the chance to witness one of the world’s greatest wildlife spectacles. This route passes through the peak migration grounds of the North Atlantic humpback whale, with incredible opportunities to see them in their breeding waters. Along the way, explore the charm of St Lucia and Martinique, then island-hop past Dominica, Guadeloupe, and St Kitts.
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Available
March 16-27 2026 -
Experience: Low to some
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Region: Caribbean & The Americas
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Coastal
The Mystery Islands of the Caribbean
10 Days from £2,399
Sail to places most travellers never see: Montserrat, Saba, Statia, Nevis, and Barbuda. Raw, beautiful islands, rich in history, character, and natural wonder. Volcanoes rise from the sea, pink-sand beaches stretch on with barely a footprint, and quiet anchorages offer solitude in these islands that most tourists never reach. From the buried city of Plymouth to the cloud forests of Saba and the wild shores of Barbuda, every island has its own story.
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Available
Tuesday 17th March 2026 - Thursday 26th March 2026 -
Experience: None
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Region: Caribbean & The Americas
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Offshore
From Mangroves to Atolls: Dominican Republic to the Bahamas
12 Days from £2,399
From sheltered mangrove bays to remote atolls rising out of thousands of feet of ocean, this voyage from the Dominican Republic to the Bahamas is a mix of island exploration, Caribbean navigation, and passage making. Possible stops en route include flamingo-filled lagoons, coral walls alive with colour, and beaches where yours are the only footprints. One or two nights will also be spent sailing through the dark under the stars on an unforgettable overnight passage.
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Available
March 31-April 11 2026 -
Experience: Low to some
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Region: Caribbean & The Americas
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Offshore
Sail Across the Atlantic Using Celestial Navigation
36 Days from £5,999
Once-in-a-lifetime Atlantic sailing adventure from the Caribbean to the United Kingdom, navigated by celestial navigation rather than GPS. Learn ancient techniques, sail the open ocean, and reconnect with nature on this unique adventure.
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Available
Friday 3rd April 2026 - Friday 8th May 2026 -
Experience: Low to some
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Region: Caribbean & The Americas
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Offshore
Chasing the Gulf Stream: Bahamas to New York City
13 Days from £2,399
Sail 1,000 miles from the Bahamas to New York City on an unforgettable offshore passage. Spend your first days exploring and training in the Bahamas before turning north for open-ocean sailing at its finest. Your route takes you past the US East Coast, with possible stops in historic Charleston, South Carolina, or Norfolk, Virginia. Make landfall in Manhattan, sailing past the Statue of Liberty, one of the most iconic arrivals in the sailing world.
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Available
April 14-26 2026 -
Experience: Low to some
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Region: Caribbean & The Americas
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Offshore
Frontier Voyage: New York to Newfoundland
17 Days from £3,999
Sail from the skyscrapers of New York to the wild cliffs of Newfoundland on a high-latitude adventure like no other. Depart past the Statue of Liberty, explore New England icons like Newport and Nantucket, then head out into the North Atlantic to Nova Scotia, Saint Pierre, and remote Newfoundland fjords. Expect whales, dolphins, seabirds, and soaring cliffs as you hone offshore skills and share in the thrill of true bluewater sailing. This is adventure sailing at its finest.
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Available
May 06 - 22 2026 -
Experience: Low to some
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Region: Norway, Iceland & The Arctic
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Offshore
Iceberg Alley: Newfoundland to Greenland
18 Days from £3,999
Sail from Newfoundland’s wild north coast to Greenland’s ice-clad fjords on this 18-day high-latitude sailing adventure. Exploring Newfoundland’s Labrador coast, we aim for Iceberg Alley where vast blue-white giants drift silently past and humpback whales breach close alongside. We then navigate the 400-mile offshore passage of the iceberg-strewn Labrador Sea, before we make landfall on Greenland’s raw and beautiful west coast, sailing and exploring a world of soaring granite cliffs, glaciers, and remote settlements.
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Available
May 26 - June 12 2026 -
Experience: Low to some
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Region: UK & Ireland
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Offshore
Sail the Atlantic in the ARC
31 Days from £5,999
Sail across the Atlantic Ocean with Rubicon 3 in the Atlantic Rally for Cruisers (ARC), a 2800-mile voyage from the Canary Islands to the Caribbean. Four weeks full of adventure, training, exhilarating sailing and memories of a lifetime.
-
Available
Wednesday 18th November 2026 - Friday 18th December 2026 -
Experience: Low to some
-
Region: Caribbean & The Americas
-
-
Caribbean Christmas & New Year Sailing: The Grenadines
12 Days from £2,499
Celebrate Christmas and New Year sailing the Grenadines. Join a hands-on adventure from St Lucia, exploring Bequia, Canouan, the Tobago Cays, Union Island and more. Swim with turtles, wander colourful island markets, and anchor beneath leaning coconut palms. Spend Christmas in tropical calm, then ring in the New Year anchored beneath Caribbean stars. No experience needed. Solo travellers welcome. A unique way to escape winter and welcome the New Year on warm trade winds and open sea.
-
Available
Monday 21st December 2026 - Friday 1st January 2027 -
Experience: None
-
-
Coastal
The Windwards Islands: Exploring the Grenadines
10 Days from £2,399
Sail the Windward Islands on a hands-on Caribbean sailing adventure. Starting in St Lucia, we island-hop south through the Grenadines, navigating crystal-clear waters, coral reefs, and secluded anchorages. Explore Bequia’s boatbuilding heritage, snorkel with turtles in the Tobago Cays, wander Union Island’s colourful markets, and anchor beneath leaning coconut palms in Salt Whistle Bay. Short distances and plenty of time ashore mean a new destination to explore each day, combining relaxed sailing with real discovery.
-
Available
Tuesday 05th January 2027 - Thursday 14th January 2027 -
Experience: None
-
Region: Caribbean & The Americas
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-
Coastal
The Windwards Islands: Exploring the Grenadines
10 Days from £2,399
Sail the Windward Islands on a hands-on Caribbean sailing adventure. Starting in St Lucia, we island-hop south through the Grenadines, navigating crystal-clear waters, coral reefs, and secluded anchorages. Explore Bequia’s boatbuilding heritage, snorkel with turtles in the Tobago Cays, wander Union Island’s colourful markets, and anchor beneath leaning coconut palms in Salt Whistle Bay. Short distances and plenty of time ashore mean a new destination to explore each day, combining relaxed sailing with real discovery.
-
Available
Tuesday 19th January 2027 - Thursday 28th January 2027 -
Experience: None
-
Region: Caribbean & The Americas
-
-
Coastal
Grenada Sailing Week
10 Days from £2,399
Grenada Sailing Week is racing without the bluster. Set deep in the southern Caribbean, between the islands of Grenada and Carriacou, it’s low-pressure, high-fun sailing at its best. Expect white sand beaches, jungle-covered hills, turquoise water, and a welcoming crowd. Each day ends with a party or beach BBQ, and the atmosphere is pure Caribbean charm. This is one of our most loved events—and easily the friendliest regatta out there.
-
Available
Friday 22nd January 2027 - Sunday 31st January 2027 -
Experience: None
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Region: Caribbean & The Americas
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-
Coastal
The Leewards: Emerald Islands Of The Caribbean
10 Days from £2,399
Sail through the Leeward Islands and explore the best of the Caribbean. Begin in St Lucia, anchoring beneath its towering volcanic peaks. In Martinique, soak up the island’s unique blend of French sophistication and Caribbean soul. Head to Dominica to paddle the winding Indian River and hike into thick rainforest. Sail on to Guadeloupe, with its mix of blissful anchorages, white sand beaches, and sleepy offshore islands. Conclude your journey in the sailing mecca of Antigua.
-
Available
Wednesday 3rd February 2027 - Friday 12th February 2027 -
Experience: None
-
Region: Caribbean & The Americas
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-
Coastal
The Mystery Islands of the Caribbean
10 Days from £2,399
Sail to places most travellers never see: Montserrat, Saba, Statia, Nevis, and Barbuda. Raw, beautiful islands, rich in history, character, and natural wonder. Volcanoes rise from the sea, pink-sand beaches stretch on with barely a footprint, and quiet anchorages offer solitude in these islands that most tourists never reach. From the buried city of Plymouth to the cloud forests of Saba and the wild shores of Barbuda, every island has its own story.
-
Available
Tuesday 16th February 2027 - Thursday 25th February 2027 -
Experience: None
-
Region: Caribbean & The Americas
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-
Offshore
RORC Caribbean 600
10 Days from £2,699
Race in the RORC Caribbean 600: Six hundred miles of exhilarating offshore racing, weaving through Caribbean islands.
-
Available
Thursday 18th February 2027 - Saturday 27th February 2027 -
Experience: Low to some
-
Region: Caribbean & The Americas
-
-
Coastal
The Leewards: Emerald Islands Of The Caribbean
10 Days from £2,399
Sail through the Leeward Islands and explore the best of the Caribbean. Begin in St Lucia, anchoring beneath its towering volcanic peaks. In Martinique, soak up the island’s unique blend of French sophistication and Caribbean soul. Head to Dominica to paddle the winding Indian River and hike into thick rainforest. Sail on to Guadeloupe, with its mix of blissful anchorages, white sand beaches, and sleepy offshore islands. Conclude your journey in the sailing mecca of Antigua.
-
Available
Tuesday 2nd March 2027 - Thursday 11th March 2027 -
Experience: None
-
Region: Caribbean & The Americas
-
-
Coastal
St Maarten Regatta
10 Days from £2,499
Join this exhilarating, week-long regatta, mixing none-too-serious but competitive yacht racing with wonderful Caribbean culture and events ashore.
-
Available
Tuesday 2nd March 2027 - Thursday 11th March 2027 -
Experience: None
-
Region: Caribbean & The Americas
-
-
Offshore
Caribbean Offshore 1000: St Lucia to Dominican Republic
12 Days from £2,399
Sail from St Lucia to the Dominican Republic on a 650nm trade-wind passage that blends fast, downwind offshore sailing with the chance to witness one of the world’s greatest wildlife spectacles. This route passes through the peak migration grounds of the North Atlantic humpback whale, with incredible opportunities to see them in their breeding waters. Along the way, explore the charm of St Lucia and Martinique, then island-hop past Dominica, Guadeloupe, and St Kitts.
-
Available
Monday 15th March 2027 - Friday 26th March 2027 -
Experience: Low to some
-
Region: Caribbean & The Americas
-
-
Coastal
The Mystery Islands of the Caribbean
10 Days from £2,399
Sail to places most travellers never see: Montserrat, Saba, Statia, Nevis, and Barbuda. Raw, beautiful islands, rich in history, character, and natural wonder. Volcanoes rise from the sea, pink-sand beaches stretch on with barely a footprint, and quiet anchorages offer solitude in these islands that most tourists never reach. From the buried city of Plymouth to the cloud forests of Saba and the wild shores of Barbuda, every island has its own story.
-
Available
Tuesday 16th March 2027 - Thursday 25th March 2027 -
Experience: None
-
Region: Caribbean & The Americas
-
-
Offshore
From Mangroves to Atolls: Dominican Republic to the Bahamas
12 Days from £2,399
From sheltered mangrove bays to remote atolls rising out of thousands of feet of ocean, this voyage from the Dominican Republic to the Bahamas is a mix of island exploration, Caribbean navigation, and passage making. Possible stops en route include flamingo-filled lagoons, coral walls alive with colour, and beaches where yours are the only footprints. One or two nights will also be spent sailing through the dark under the stars on an unforgettable overnight passage.
-
Available
Tuesday 30th March 2027 - Saturday 10th April 2027 -
Experience: Low to some
-
Region: Caribbean & The Americas
-
-
Offshore
Sail Across the Atlantic Using Celestial Navigation
36 Days from £5,999
Once-in-a-lifetime Atlantic sailing adventure from the Caribbean to the United Kingdom, navigated by celestial navigation rather than GPS. Learn ancient techniques, sail the open ocean, and reconnect with nature on this unique adventure.
-
Available
Friday 02nd April 2027 - Friday 7th May 2027 -
Experience: Low to some
-
Region: Caribbean & The Americas
-
-
Offshore
Chasing the Gulf Stream: Bahamas to New York City
13 Days from £2,399
Sail 1,000 miles from the Bahamas to New York City on an unforgettable offshore passage. Spend your first days exploring and training in the Bahamas before turning north for open-ocean sailing at its finest. Your route takes you past the US East Coast, with possible stops in historic Charleston, South Carolina, or Norfolk, Virginia. Make landfall in Manhattan, sailing past the Statue of Liberty, one of the most iconic arrivals in the sailing world.
-
Available
Tuesday 13th April 2027 - Saturday 25th April 2027 -
Experience: Low to some
-
Region: Caribbean & The Americas
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-
Offshore
Frontier Voyage: New York to Newfoundland
17 Days from £3,999
Sail from the skyscrapers of New York to the wild cliffs of Newfoundland on a high-latitude adventure like no other. Depart past the Statue of Liberty, explore New England icons like Newport and Nantucket, then head out into the North Atlantic to Nova Scotia, Saint Pierre, and remote Newfoundland fjords. Expect whales, dolphins, seabirds, and soaring cliffs as you hone offshore skills and share in the thrill of true bluewater sailing. This is adventure sailing at its finest.
-
Available
Wednesday 5th May 2027 - Friday 21st May 2027 -
Experience: Low to some
-
Region: Norway, Iceland & The Arctic
-
-
Offshore
Iceberg Alley: Newfoundland to Greenland
18 Days from £3,999
Sail from Newfoundland’s wild north coast to Greenland’s ice-clad fjords on this 18-day high-latitude sailing adventure. Exploring Newfoundland’s Labrador coast, we aim for Iceberg Alley where vast blue-white giants drift silently past and humpback whales breach close alongside. We then navigate the 400-mile offshore passage of the iceberg-strewn Labrador Sea, before we make landfall on Greenland’s raw and beautiful west coast, sailing and exploring a world of soaring granite cliffs, glaciers, and remote settlements.
-
Available
Tuesday 25th May 2027 - Friday 11th June 2027 -
Experience: Low to some
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Region: UK & Ireland
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Coastal
1 Week Sailing Vacation in the Bahamas
34 Days from £10
Experience paradise with a week-long Bahamas sailing adventure. Sail in crystal-clear waters, wander sun-kissed beaches, dive on coral reefs, and discover paradise islands. 1 week of tropical bliss and unforgettable sailing.
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Available
30 January 2028 - 03 March 2028 -
Experience: None
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Region: Caribbean & The Americas
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