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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

    Tall Ship Taster Sailing in Scotland

    Tall Ship Taster Sailing in Scotland

    • 13 June 2023, 4 days
    • Vessel: Blue Clipper
    • Port: Oban, Scotland
    £870.00 Details
    Luxury Sailing from Croatia to Sicily

    Luxury Sailing from Croatia to Sicily

    • 19 August 2023, 8 days
    • Vessel: Kairós
    • Port: Croatia/Italy
    £2,785.00 Details
    Sailing the Isles of Scilly with Bessie Ellen

    Sailing the Isles of Scilly with Bessie Ellen

    • 10 August 2023, 7 days
    • Vessel: Bessie Ellen
    • Port: Newlyn, Cornwall
    £1,312.00 Details
    Private Charter in the Lofoten Islands

    Private Charter in the Lofoten Islands

    • 3 September 2023, 6 days
    • Vessel: Stella Oceana
    • Port: Norway
    On request Details
    Private Charter in the Lofoten Islands

    Private Charter in the Lofoten Islands

    • 4 August 2024, 6 days
    • Vessel: Stella Oceana
    • Port: Norway
    On request Details
    Luxury Sailing from Sicily

    Luxury Sailing from Sicily

    • 6 September 2023, 10 days
    • Vessel: Kairós
    • Port: Sicily, Italy
    £3,870.00 Details
    Sailing the Baltic Sea & Exploring Denmark

    Sailing the Baltic Sea & Exploring Denmark

    • 22 May 2023, 6 days
    • Vessel: Eye of the Wind
    • Port: Flensburg, Germany
    £1,525.00 Details
    Expedition Sailing from Tromsø to Svalbard

    Expedition Sailing from Tromsø to Svalbard

    • 24 April 2023, 9 days
    • Vessel: Valiente
    • Port: Norway/Svalbard
    £2,695.00 Details
    Whale Shark & Wildlife Watching in Indonesia

    Whale Shark & Wildlife Watching in Indonesia

    • 5 December 2023, 10 days
    • Vessel: Ombak Putih
    • Port: West Papau, Indonesia
    £6,295.00 Details
    Luxury Sailing & Island Hopping from Santorini

    Luxury Sailing & Island Hopping from Santorini

    • 21 September 2024, 8 days
    • Vessel: Rhea
    • Port: Santorini, Greece
    £2,900.00 Details
    Sailing the Indonesian Wonders; Whale Sharks, Dragons & Coral Reefs

    Sailing the Indonesian Wonders; Whale Sharks, Dragons & Coral Reefs

    • 26 August 2023, 8 days
    • Vessel: Ombak Putih
    • Port: Indonesia
    £3,895.00 Details
    Sailor’s Voyage to Cornwall

    Sailor’s Voyage to Cornwall

    • 2 June 2023, 5 days
    • Vessel: Maybe
    • Port: Scotland/Cornwall
    £695.00 Details

    Search for more in our Voyage Finder

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    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

    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.

    Scotland and the Hebrides Wildlife Guide

    Read more
    Indonesia Komodo islands anchorage

    Why sailing in Indonesia should be on your holiday bucket list!

    Read more
    View of Salt Whistle Bay, Mayreau, Caribbean

    A Guide to Sailing in St Vincent & the Grenadines

    Read more
    St George's Harbour, Grenada, Caribbean

    A Guide to a Sailing in Grenada

    Read more
    View the whole log
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    • Search all Voyages
    • Fleet
      • See Our Fleet
        • Agnes
        • Bessie Ellen
        • Blue Clipper
        • Cherokee
        • Chronos
        • Escape
        • Eye of the Wind
        • Florette
        • Flying Dutchman
        • Grayhound
        • Iris
        • Kairós
        • Katharina
        • Maybe
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        • Ombak Putih
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        • Pellew
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        • Rhea
        • Skyelark
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        • Unity
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