This month-long sailing expedition follows Scotland’s famous North Coast 500, reworked as a hands-on voyage by sea and recently featured in a full double-page spread in Yachting Monthly. Leg 1 and Leg 3 of the 2026 expedition are now fully booked, with just one cabin remaining on Leg 2, while dates for 2027 are already available to book. Sail one section or join the full journey and experience Scotland’s coastline, islands, and canals from the deck of a purpose-built expedition yacht.
Overview
Starting in Oban, home to the renowned whisky distillery, this adventure takes you through Scotland’s rugged beauty in three distinct 10-day legs. Sail to the Hebrides, explore the Orkney Isles, and return to Oban via the iconic Caledonian Canal. Each leg is tailored to the weather, crew preferences, and the expertise of our world-class skipper, Jim Dobie, an RYA Yachtmaster Examiner with unparalleled experience.
Perfect for adventurers of all levels, this trip welcomes beginners and seasoned sailors alike. For those looking to develop their skills, our skipper will provide tailored learning opportunities throughout the journey.
Highlights
- Hands-On Sailing: Get involved in all aspects of sailing under expert guidance, with opportunities to learn navigation and seamanship.
- Stunning Scottish Scenery: From the Hebrides to the Orkney Isles, experience Scotland’s remote beauty and vibrant coastal towns.
- Comfortable Yacht: Sail aboard Big Blue, a spacious and fully equipped Beneteau Oceanis 523 with en-suite cabins and plenty of room for six guests.
- Tailored Experience: Flexible itineraries adapt to the crew’s preferences and weather conditions.
Itinerary
Leg 1: Oban to Stornoway
- Highlights: Explore Tobermory, the Isles of Rum, Muck, Eigg, and the Shiant Isles.
- Overview: Sail through the Hebrides, with time ashore in beautiful coastal villages. Enjoy challenging winds and tides with plenty of space aboard *Big Blue*.
Leg 2: Stornoway to Oban (One Cabin Remaining – 2026)
- Highlights: Cape Wrath sailing, remote west coast anchorages, and the Caledonian Canal
- Overview: This is now the only available leg in 2026 and has been revised to finish in Oban rather than Wick. From Stornoway, the route heads south via Scotland’s wild north-west coast before entering the Caledonian Canal and passing through Loch Ness. This leg balances demanding open-water sailing with sheltered inland waterways and offers a complete sense of the journey.
Leg 3: Kirkwall to Oban via Caledonian Canal
- Highlights: Cruise through Wick, Inverness, and the Caledonian Canal, a bucket-list destination for sailors.
- Overview: A mix of coastal and inland sailing, including Loch Ness, completes this epic tour of Scotland.
Your Yacht: Big Blue
Big Blue is a Beneteau Oceanis 523, designed for long voyages in comfort.
It features:
- Spacious Cabins: Three en-suite double cabins (convertible to twin), plus a separate skipper’s cabin.
- Onboard Comfort: Heating in all cabins, private bathrooms, and ample storage space.
- Adventure Ready: Equipped with a paddleboard, inflatable kayak, and full offshore gear for exploring anchorages.
Accommodation Options
- Single Berth: A comfortable individual berth for solo travellers.
- Double Cabin: Perfect for couples or friends, with the option to book the cabin as private.
Why Choose This Adventure?
- Expert Leadership: Sail with Jim Dobie, a globally experienced skipper and RYA Yachtmaster Examiner.
- Customised Itinerary: No two trips are the same, as each leg adapts to the crew’s preferences.
- Unique Perspective: Experience Scotland’s famous North Coast 500 by sea, with unparalleled views and access.
- All Levels Welcome: Whether you're a beginner or a seasoned sailor, this trip is tailored to suit your skills and goals.
Booking Options
- Leg 1: Oban to Stornoway
- Leg 2: Stornoway to Kirkwall
- Leg 3: Kirkwall to Oban via Caledonian Canal
- Full Expedition: All Three Legs
Each leg lasts 10 days, with a few days between for crew changeovers. Guests joining the full expedition stay aboard Big Blue throughout, keeping their same berth for the entire month.
Book Your Adventure
Reserve your place now for this unique sailing journey through Scotland’s most stunning landscapes. Whether you join for a single leg or the full expedition, this North Coast 500 Sailing Adventure promises an unforgettable experience on the water.
Secure your spot today!