Scotland's Northern Islands Challenge

Set sail on a thrilling adventure “up North” as we “head south” charting a course through some of Scotland’s most breath-taking and remote islands. Your journey begins in Lerwick, the bustling capital of Shetland, steeped in rich history and surrounded by untamed natural beauty, including some of Scotland’s best wildlife. 

After the opportunity to explore a bit of Shetland, our first offshore leg will take us south, leaving the rugged shores of Shetland behind. If the weather is on our side, we’ll make a special stop on Fair Isle, a bucket-list destination for many. Here, you’ll have the rare chance to explore a place that feels like stepping into another world—a truly once-in-a-lifetime experience.

Continuing our journey south, we’ll target the northern shores of the Orkney Islands. Expect jaw-dropping scenery, with the possibility of encountering incredible wildlife at every turn—breath-taking cliffs, serene coves, and untamed landscapes. When we arrive in Kirkwall, the Orkney capital, you’ll have time to dive into the town’s vibrant history. Perhaps visit the prehistoric Skara Brae, the iconic Italian Chapel, the famous Scapa Flow or maybe even visit the distillery before we slip the lines and head out for the final leg of our voyage. 

The last stretch of our journey will see us crossing the powerful tidal currents of the Pentland Firth, bound for the Highland capital of Inverness. Along the way, we’ll pass some of Scotland’s most iconic locations, and with the skipper carefully watching the weather to make the best routing decisions, you’ll be in for a ride filled with anticipation. Once we arrive at Inverness Marina, we’ll be ready to celebrate the completion of this unforgettable journey through Scotland’s wildest and most beautiful islands!

Want to go monster spotting with us? Click here to find out more about our next leg, the canal cruise south to the west coast town of Oban, taking in the famous Loch Ness.

Key Information

Travel:

Lerwick

Lerwick, the vibrant capital of Shetland, is well-connected with frequent ferry services and regular flights from Sumburgh Airport, providing convenient links back to the Scottish mainland and offering access to national and international travel connections.

Inverness

Inverness, the cultural heart of the Scottish Highlands, boasts impressive transport links, with regular flights, scenic rail routes, and ferry connections reaching across the UK and to select international destinations.

Event Information:

Check out the links below for helpful details on what to bring, our exciting provisional itinerary, and everything you need to know to join us on this adventure. We can’t wait to welcome you aboard!

What to bring guidance is located here.

Our Provisional Itinerary will be available here from October 2026

Joining Instructions will be available here from October 2026

Cost: £1740 before early booking discount

Book with 25% off from £1305 until 30 November 2025 (£350 deposit due at time of booking) per person inclusive of all onboard costs. Discount reduces on the 1st of each month by 5% until 1 April 2026 when the full price will apply. Additional chargeable options are available for cabin types, selectable when booking.

Dates:

14th - 25th August 2026.

Sample Itinerary:

Day One: Arrive aboard the yacht in the late afternoon, where you'll be welcomed by our friendly crew for an evening meal and a chance to get familiar with your new floating home. Unpack, unwind and get ready for an unforgettable week.

Day Two: Start the adventure with a mandatory safety briefing, followed by a final familiarisation session as we set sail out of Lerwick and head South to explore the wonders of this stunning island group.

Day Three to Four: Keep your wildlife spotting eyes out for the many species that make Shetland a nature lover’s dream as we make our way down to the Fair Isle, one of Scotland’s most remote inhabited islands. If the weather is kind, time will be made to ensure you make the most of your visit to this region with an expedition ashore on Fair Isle. Not just famous for woolly jumpers, although they are a great purchase, enjoy a hike along the beautifully rugged coastline, encounter some of the impressive local wildlife or visit the museum which offers an informative insight in the history of life on the island.

Day Five to Eight: The final leg of our adventure in the islands! We’ll continue south, sailing to Orkney, with a hopeful visit to some of the outlying islands. Orkney offers plenty of stunning, sheltered anchorages for the night, but we’ll make sure you get some well-earned time ashore in Kirkwall to explore the sights. Don’t miss the chance to visit the fascinating Neolithic village of Skara Brae!

Day Nine to Eleven: We’ll say goodbye to the islands as we head south towards the Scottish mainland, carefully timing our crossing of the Pentland Firth to take advantage of favourable tides. Our final destination will be Inverness Marina, where we’ll celebrate the completion of our voyage with an evening ashore. As we enter the Moray Firth, keep an eye out for the resident pod of Bottlenose Dolphins—some of the largest of their species!

Day Twelve: Enjoy one last tasty breakfast, then disembark by noon, taking with you unforgettable memories of your Northern Islands Challenge adventure.

NOTE:

• The cost of this event includes all onboard food, fuel, waterproof and lifejacket hire and berthing charges.

• We supply pillows and sleeping bags

• Sailing activity is weather dependent. If conditions are too severe activity may be postponed, cancelled or the passage plan adjusted.

• Guests will need to arrange their own travel to and from the embarkation and disembarkation points.

• Unlike many companies, we don’t use your payment before your trip. This means if unexpected disruptions occur that qualify for a refund, your money is safe with us and will be returned quickly and hassle-free. (We also don’t charge a cleaning fee, or make you do the cleaning.. Bonus :-))