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    Adventure Sailing Holidays

    Climb aboard classic ships, luxury yachts or adventure vessels and explore a host of destinations as you’ve never seen them before. Let our fleet of boats give you an authentic taste of life under sail as you learn the ropes and experience a sailing holiday like no other. All our voyages are fully crewed so there’s no sailing experience needed to join a sailing holiday adventure!

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    Featured Sailing Holidays

    Sailing the Channel Islands & Normandy

    Sailing the Channel Islands & Normandy

    • 24 August 2023, 14 days
    • Vessel: Pilgrim of Brixham
    • Port: Brixham, Devon
    £1,750.00 Details
    Tall Ship Taster Sailing in Portugal

    Tall Ship Taster Sailing in Portugal

    • 29 September 2023, 5 days
    • Vessel: Maybe
    • Port: Portugal
    £900.00 Details
    Luxury Sailing in the Caribbean

    Luxury Sailing in the Caribbean

    • 19 February 2023, 8 days
    • Vessel: Chronos
    • Port: Grenada, Caribbean
    £2,785.00 Details
    Sailing the Outer Hebrides, Shiants or Skye

    Sailing the Outer Hebrides, Shiants or Skye

    • 19 May 2023, 7 days
    • Vessel: Zuza
    • Port: Oban, Scotland
    £1,420.00 Details
    Luxury Classic Yacht Sailing from Corfu

    Luxury Classic Yacht Sailing from Corfu

    • 3 June 2023, 8 days
    • Vessel: Kairós
    • Port: Corfu, Greece
    £2,785.00 Details
    Private Charter in the Lofoten Islands

    Private Charter in the Lofoten Islands

    • 30 June 2023, 6 days
    • Vessel: Stella Oceana
    • Port: Norway
    On request Details
    Offshore Passage Sailing to the Canary Islands

    Offshore Passage Sailing to the Canary Islands

    • 30 October 2023, 13 days
    • Vessel: Eye of the Wind
    • Port: Spain/Lanzarote
    £2,360.00 Details
    Sailing the Spanish coast, Rias Baxas

    Sailing the Spanish coast, Rias Baxas

    • 5 July 2023, 8 days
    • Vessel: Skyelark
    • Port: Vigo, Spain
    £2,200.00 Details
    Tall Ship Sailing the Outer Hebrides & St Kilda

    Tall Ship Sailing the Outer Hebrides & St Kilda

    • 21 May 2023, 10 days
    • Vessel: Blue Clipper
    • Port: Oban, Scotland
    £2,545.00 Details
    Scandinavian Tall Ship Sailing

    Scandinavian Tall Ship Sailing

    • 29 July 2023, 8 days
    • Vessel: Eye of the Wind
    • Port: Sweden/Germany
    £2,135.00 Details
    Tall Ship Sailing Skye & the Small Isles

    Tall Ship Sailing Skye & the Small Isles

    • 18 August 2023, 7 days
    • Vessel: Blue Clipper
    • Port: Mallaig, Scotland
    £1,760.00 Details
    Sailing the Firth of Clyde

    Sailing the Firth of Clyde

    • 18 May 2023, 6 days
    • Vessel: Maybe
    • Port: Firth of Clyde, Scotland
    £1,210.00 Details

    Search for more in our Voyage Finder

    Destinations main page

    Destinations

    Our range of vessels enables us to offer several destinations all over the globe. Which sailing holiday will you choose?

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    Our Fleet main page

    Our Fleet

    With vessels of all sizes and each with a unique history and construction, there is no shortage of choice for your sailing holiday.

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    “I’ve never sailed before, but if this is sailing, then I’m addicted. So, it seems, is everyone else: 85% of the Bessie Ellen’s guests return for further sailing adventures.”Hazel Southam, writing for The Guardian
    “Having never set foot on a working tall ship, I had no idea what to expect aside from what I had seen in films. The reality is so much better. I would recommend anyone who loves the sea to try this.”Chris Baker, Muddy Stilettos Cornwall
    “This was the Canaries of riding anchor in moonlit bays...., of swimming with turtles and and admiring pilot whales beneath our bows.”Andrew Eames, writing for The Times
    “I thoroughly enjoyed reliving my youth onboard Bessie Ellen. We came from Cornwall to Oban on this beautiful ship with Skipper Nikki and her brilliant crew. Great hands on sailing, relaxed atmosphere and fabulous food. A true get away.”Kate Smith, Bessie Ellen Guest

    Latest from our Adventure Journal

    Be inspired to discover the world under sail! Read our latest journals below.

    St Lucia Caribbean Marigot bay unsplash

    10 of our favourite Caribbean anchorages, beaches and bays

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    flensburg germany baltic sea

    Our Top 5 Destinations for a Sailing Holiday in Germany

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    MED aeolian Islands

    Your guide to a Sailing Holiday in the Aeolian Islands

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    Noorderlicht Svalbard Hiking Guests

    Everything you need to know before you visit Svalbard

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    View the whole log
    Fleet of traditional ships

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    We can make to your boat charter business plain sailing.

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    Why book with us?

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    • Fleet
      • See Our Fleet
        • Agnes
        • Bessie Ellen
        • Blue Clipper
        • Cherokee
        • Chronos
        • Escape
        • Eye of the Wind
        • Florette
        • Flying Dutchman
        • Grayhound
        • Iris
        • Kairós
        • Katharina
        • Maybe
        • Noorderlicht
        • Ombak Putih
        • Oosterschelde
        • Pellew
        • Pilgrim of Brixham
        • Rhea
        • Skyelark
        • Steady
        • Stella Oceana
        • Stravaigin
        • Twister
        • Unity
        • Valiente
        • Zorba
        • Zuza
        • Back
      • See boats by type
        • Adventure Vessels
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    • Destinations
      • UK
        • Channel Islands
        • Cornwall
        • Devon
        • Isles of Scilly
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        • Scotland – Firth of Clyde
        • Back
      • Europe
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