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Sailing Events and Opportunities by Wavysail

  • Scotland: Sail Oban to Stornoway

    2025, Sat Aug 02 10:00am - Mon Aug 11
    image of Scotland: Sail Oban to Stornoway
    Category Type
    Skippered/Crewed Charter Vacation
    By the Cabin
    Start Location
    United Kingdom, Oban, Argyll
    Contacts
    Heather Deary,
    Ph: +44 7753454988,
    email: heather@wavysail.com
    Price
    US$4,114.83 per person
    Embark on an unforgettable adventure as we reimagine Scotland’s iconic North Coast 500 - this time, under sail aboard Big Blue, our stunning expedition yacht. Your journey begins in the coastal town of Oban, famed for its historic whisky distillery. After a comprehensive safety briefing and gear check, we hoist the sails and head north. The exact route is shaped by the weather and the spirit of the crew, but may include magical stops at Tobermory, the wild isles of Rum, Muck and Eigg, the hauntingly beautiful Shiant Isles, and finally, Stornoway in the Outer Hebrides. This is some of the UK’s most spectacular sailing terrain - dramatic coastlines, shifting tides, and ever-changing winds, paired with remote anchorages and unforgettable overnight spots. With only six guests on board, Big Blue offers space, comfort, and a sense of true expedition sailing. Whether you’re a complete beginner or a seasoned sailor, our professional skippers tailor the experience to suit you - offering hands-on learning, navigation skills, and the freedom to be as involved as you like. Link to more information about this Opportunity.

  • Scotland: Sail Stornoway to Kirkwall

    2025, Thu Aug 14 10:00am - Sat Aug 23
    image of Scotland: Sail Stornoway to Kirkwall
    Category Type
    Skippered/Crewed Charter Vacation
    By the Cabin
    Start Location
    United Kingdom, Stornoway, Roos-shire
    Contacts
    Heather Deary,
    Ph: +44 7753454988,
    email: heather@wavysail.com
    Price
    US$4,114.83 per person
    Set sail on a breathtaking twist of Scotland’s legendary North Coast 500 - aboard Big Blue, our beautifully equipped expedition yacht. Join one leg, combine it with a scenic drive, or experience the full sailing journey along this epic coastal route. Leg 2 takes you into the wild and remote Orkney Isles. As Leg 1 wraps up, we welcome new crew with a full yacht induction and safety briefing, ensuring everyone feels confident and ready to sail. Departing from Stornoway, we navigate north past stunning landscapes, stopping at Lochinver - home to the world’s most famous pies! From there, we sail around the dramatic headlands of Cape Wrath and make our crossing to Stromness, before arriving in the historic harbour of Kirkwall, the heart of Orkney. This leg offers incredible variety - open water sailing, unique coastal towns, and the chance to experience one of Scotland’s most remote island groups from the sea. With great onward travel options from Kirkwall, you can disembark - or, better yet, stay aboard for Leg 3 and continue the expedition. Link to more information about this Opportunity.

  • Scotland: Sail Kirkwall to Oban (via the Caledonian Canal)

    2025, Wed Aug 27 10:00am - Fri Sep 05
    image of Scotland: Sail Kirkwall to Oban (via the Caledonian Canal)
    Category Type
    Skippered/Crewed Charter Vacation
    By the Cabin
    Start Location
    United Kingdom, Kirkwall
    Contacts
    Heather Deary,
    Ph: +44 7753454988,
    email: heather@wavysail.com
    Price
    US$4,114.83 per person
    Join the final leg of our extraordinary sailing journey along Scotland’s iconic North Coast 500 - reimagined by sea aboard Big Blue, our elegant expedition yacht. Whether you’ve joined earlier legs or are stepping aboard for the first time, this is a spectacular way to experience Scotland’s rugged northern coast and inland waterways. Leg 3 begins in Kirkwall, the vibrant capital of the Orkney Isles. After welcoming the new crew and completing a detailed yacht induction and safety briefing, we set sail southward. Our route takes us past the historic port of Wick and into Inverness, gateway to the Highlands, before we enter the legendary Caledonian Canal - one of the most scenic and storied waterways in the world. This leg is a true bucket list adventure for sailors, blending offshore sailing with inland cruising, all set against breathtaking Scottish landscapes. The exact itinerary may vary based on weather and crew preferences, allowing for a dynamic, personalised experience. We end our journey in Oban, completing a full circumnavigation of Scotland’s magnificent northern coast by sea - an unforgettable expedition for adventurers, explorers, and lovers of wild places. Link to more information about this Opportunity.

  • South Atlantic Expedition: Cape Town to St Helena

    2025, Mon Oct 27 10:00am - Sat Dec 13
    image of South Atlantic Expedition: Cape Town to St Helena
    Category Type
    Skippered/Crewed Charter Vacation
    By the Cabin
    Start Location
    South Africa, Cape Town, Western Cape
    Contacts
    Heather Deary,
    Ph: +44 7753454988,
    email: heather@wavysail.com
    Price
    US$9,610.43 per person
    Embark on a truly extraordinary sailing expedition across the South Atlantic - designed not just to challenge and inspire, but to teach you exactly what it takes to plan and complete a major ocean crossing. Led by a highly experienced skipper and first mate, this is far more than a sailing trip - it’s an immersive ocean adventure. Split into two distinct legs, you can join either one or experience the full return journey, including time ashore on the legendary island of St Helena. Each leg includes around five days exploring the island, with bed and breakfast accommodation included in the voyage cost. Leg 1: Cape Town to St Helena (Approx. 4 Weeks) Your journey begins in Cape Town with “Prep Week” at the Royal Cape Yacht Club, where you'll gain hands-on training in route planning, weather systems, provisioning, and offshore safety - everything needed for a successful ocean voyage. We then set sail along the rugged African coast, stopping in Lüderitz, Namibia. Here, you can log qualifying 60nm passages for your sailing certifications and explore the haunting desert ghost town of Kolmanskop. The voyage then crosses the open South Atlantic to the remote island of St Helena - a sub-tropical gem steeped in history. You’ll enjoy five full days ashore before choosing to fly back to Johannesburg or continue on to Leg 2. Leg 2: St Helena to Cape Town via Tristan Da Cunha (Approx. 5 Weeks) Leg 2 begins with five immersive days on St Helena Island as the new crew settles in, prepares Aurora for the return, and connects with those finishing Leg 1. From there, we head west into deep ocean before turning south toward the remote volcanic archipelago of Tristan da Cunha - one of the world’s most isolated destinations. Expect dynamic weather, powerful seas, and incredible learning opportunities, including celestial navigation and deep-ocean routing. This leg includes over 1,500 nautical miles and qualifies as an RYA mileage trip for aspiring ocean sailors. Full Expedition: 4,500nm | 48 Days Those joining both legs will complete nearly 4,500 nautical miles over 48 days - earning skills, sea time, and unforgettable memories. Whether you’re seeking to develop as an offshore sailor or simply craving a once-in-a-lifetime sailing adventure, this South Atlantic crossing offers the real deal. Link to more information about this Opportunity.