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.

Read our full guide on the Caribbean here.

35 Items

  • sailing the atlantic
    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.

    • Calendar icon

      Join Waitlist

      Wednesday 19th November 2025 - Friday 19th December 2025
    • Medal icon
      Experience: Low to some
    • Pin icon
      Region: Caribbean & The Americas
  • christmas sailing in the caribbean

    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.

    • Calendar icon

      Available

      Tuesday 23rd December 2025 - Saturday 3rd January 2026
    • Medal icon
      Experience: None
  • caribbean sailing vacation
    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.

    • Calendar icon

      Available

      Tuesday 6th January 2026 - Thursday 15 January 2026
    • Medal icon
      Experience: None
    • Pin icon
      Region: Caribbean & The Americas
  • caribbean sailing vacation
    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.

    • Calendar icon

      Available

      January 20-29 2026
    • Medal icon
      Experience: None
    • Pin icon
      Region: Caribbean & The Americas
  • Grenada Sailing Week
    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.

    • Calendar icon

      2 Places Available

      Friday 23rd January 2026 - Sunday 1st February 2026
    • Medal icon
      Experience: None
    • Pin icon
      Region: Caribbean & The Americas
  • caribbean sailing holiday
    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.

    • Calendar icon

      Available

      Wednesday 4th February 2026 - Friday 13th February 2026
    • Medal icon
      Experience: None
    • Pin icon
      Region: Caribbean & The Americas
  • Montserrat
    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.

    • Calendar icon

      Available

      Tuesday 17th February 2026 - Thursday 26th February
    • Medal icon
      Experience: None
    • Pin icon
      Region: Caribbean & The Americas
  • rorc caribbean 600
    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.

    • Calendar icon

      Join Waitlist

      Thursday 19th February 2026 - Saturday 28th February 2026
    • Medal icon
      Experience: Low to some
    • Pin icon
      Region: Caribbean & The Americas
  • st maarten regatta header
    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.

    • Calendar icon

      Available

      Tuesday 3rd March 2026 - Friday 13th March 2026
    • Medal icon
      Experience: None
    • Pin icon
      Region: Caribbean & The Americas
  • caribbean sailing holiday
    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.

    • Calendar icon

      Available

      March 03-12 2026
    • Medal icon
      Experience: None
    • Pin icon
      Region: Caribbean & The Americas
  • Drone shot of yacht
    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.

    • Calendar icon

      Available

      March 16-27 2026
    • Medal icon
      Experience: Low to some
    • Pin icon
      Region: Caribbean & The Americas
  • Montserrat
    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.

    • Calendar icon

      Available

      Tuesday 17th March 2026 - Thursday 26th March 2026
    • Medal icon
      Experience: None
    • Pin icon
      Region: Caribbean & The Americas
  • Bahamas
    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.

    • Calendar icon

      Available

      March 31-April 11 2026
    • Medal icon
      Experience: Low to some
    • Pin icon
      Region: Caribbean & The Americas
  • celestial navigation mid atlantic
    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.

    • Calendar icon

      Available

      Friday 3rd April 2026 - Friday 8th May 2026
    • Medal icon
      Experience: Low to some
    • Pin icon
      Region: Caribbean & The Americas
  • Sailing into new york
    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.

    • Calendar icon

      Available

      April 14-26 2026
    • Medal icon
      Experience: Low to some
    • Pin icon
      Region: Caribbean & The Americas
  • arctic sailing adventure
    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.

    • Calendar icon

      Available

      May 06 - 22 2026
    • Medal icon
      Experience: Low to some
    • Pin icon
      Region: Norway, Iceland & The Arctic
  • Greenland
    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.

    • Calendar icon

      Available

      May 26 - June 12 2026
    • Medal icon
      Experience: Low to some
    • Pin icon
      Region: UK & Ireland
  • sailing the atlantic
    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.

    • Calendar icon

      Available

      Wednesday 18th November 2026 - Friday 18th December 2026
    • Medal icon
      Experience: Low to some
    • Pin icon
      Region: Caribbean & The Americas
  • christmas sailing in the caribbean

    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.

    • Calendar icon

      Available

      Monday 21st December 2026 - Friday 1st January 2027
    • Medal icon
      Experience: None
  • caribbean sailing vacation
    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.

    • Calendar icon

      Available

      Tuesday 05th January 2027 - Thursday 14th January 2027
    • Medal icon
      Experience: None
    • Pin icon
      Region: Caribbean & The Americas
  • caribbean sailing vacation
    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.

    • Calendar icon

      Available

      Tuesday 19th January 2027 - Thursday 28th January 2027
    • Medal icon
      Experience: None
    • Pin icon
      Region: Caribbean & The Americas
  • Grenada Sailing Week
    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.

    • Calendar icon

      Available

      Friday 22nd January 2027 - Sunday 31st January 2027
    • Medal icon
      Experience: None
    • Pin icon
      Region: Caribbean & The Americas
  • caribbean sailing holiday
    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.

    • Calendar icon

      Available

      Wednesday 3rd February 2027 - Friday 12th February 2027
    • Medal icon
      Experience: None
    • Pin icon
      Region: Caribbean & The Americas
  • Montserrat
    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.

    • Calendar icon

      Available

      Tuesday 16th February 2027 - Thursday 25th February 2027
    • Medal icon
      Experience: None
    • Pin icon
      Region: Caribbean & The Americas
  • rorc caribbean 600
    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.

    • Calendar icon

      Available

      Thursday 18th February 2027 - Saturday 27th February 2027
    • Medal icon
      Experience: Low to some
    • Pin icon
      Region: Caribbean & The Americas
  • caribbean sailing holiday
    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.

    • Calendar icon

      Available

      Tuesday 2nd March 2027 - Thursday 11th March 2027
    • Medal icon
      Experience: None
    • Pin icon
      Region: Caribbean & The Americas
  • st maarten regatta header
    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.

    • Calendar icon

      Available

      Tuesday 2nd March 2027 - Thursday 11th March 2027
    • Medal icon
      Experience: None
    • Pin icon
      Region: Caribbean & The Americas
  • Drone shot of yacht
    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.

    • Calendar icon

      Available

      Monday 15th March 2027 - Friday 26th March 2027
    • Medal icon
      Experience: Low to some
    • Pin icon
      Region: Caribbean & The Americas
  • Montserrat
    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.

    • Calendar icon

      Available

      Tuesday 16th March 2027 - Thursday 25th March 2027
    • Medal icon
      Experience: None
    • Pin icon
      Region: Caribbean & The Americas
  • Bahamas
    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.

    • Calendar icon

      Available

      Tuesday 30th March 2027 - Saturday 10th April 2027
    • Medal icon
      Experience: Low to some
    • Pin icon
      Region: Caribbean & The Americas
  • celestial navigation mid atlantic
    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.

    • Calendar icon

      Available

      Friday 02nd April 2027 - Friday 7th May 2027
    • Medal icon
      Experience: Low to some
    • Pin icon
      Region: Caribbean & The Americas
  • Sailing into new york
    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.

    • Calendar icon

      Available

      Tuesday 13th April 2027 - Saturday 25th April 2027
    • Medal icon
      Experience: Low to some
    • Pin icon
      Region: Caribbean & The Americas
  • arctic sailing adventure
    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.

    • Calendar icon

      Available

      Wednesday 5th May 2027 - Friday 21st May 2027
    • Medal icon
      Experience: Low to some
    • Pin icon
      Region: Norway, Iceland & The Arctic
  • Greenland
    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.

    • Calendar icon

      Available

      Tuesday 25th May 2027 - Friday 11th June 2027
    • Medal icon
      Experience: Low to some
    • Pin icon
      Region: UK & Ireland
  • Bahamas
    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.

    • Calendar icon

      Available

      30 January 2028 - 03 March 2028
    • Medal icon
      Experience: None
    • Pin icon
      Region: Caribbean & The Americas