Tall Ship Sailing the Outer Hebrides and St Kilda

Sailing the Outer Hebrides: Oban to the Atlantic Islands

Oban → Inner Hebrides → Harris and Lewis → North Uist → South Uist → Eriskay → Barra → St Kilda → Ullapool

Flying Dutchman departs Oban, a natural gateway to the Hebrides on Scotland’s west coast, and heads north and west into some of the most rewarding sailing waters in Britain. The Outer Hebrides stretch along Scotland’s Atlantic frontier, a chain of islands with a long history of human habitation, extraordinary nature and a sense of space and quiet that is increasingly rare. Wind and tide lead the way on this voyage, with the crew shaping each day’s sailing around the elements and the opportunities they bring.

The largest island in the chain is Harris and Lewis, two distinct landscapes on a single island. Lewis is flatter, with the remarkable Callanish Standing Stones rising from the moorland, a Neolithic site estimated to be around 6,000 years old. Harris has more mountains and cliffs, a dramatic Atlantic coastline and the celebrated Harris Distillery, known as much for its gin as for the island’s famous tweed. Stornoway, the largest town, offers shops, restaurants and museums for those who want time to explore ashore.

The Southern Isles: Uist, Eriskay and Barra

Heading south through the chain, the islands shift in character at every turn. North Uist is flat and marsh-rich, an important habitat for rare bird species, with archaeological finds scattered across the island including burial mounds, stone circles and standing stones. Most of the 1,500 or so inhabitants of Lochmaddy still speak Gaelic, and the island carries its ancient culture lightly but proudly.

South Uist rises to hills of 600 metres on the eastern side, with dramatic coastlines giving way to an almost unbroken stretch of Atlantic beach on the west. Between South Uist and Barra lies Eriskay, whose inhabitants lived from fishing for centuries and where, in 1941, the ship SS Politician ran aground with 20,000 barrels of whisky on board, an event that inspired the film Whisky Galore.

Barra, one of the southernmost islands of the Outer Hebrides, is known for its azure sea, white beaches and sweeping views. It is also home to the only commercial airport in the world where planes land on the beach at low tide.

• Callanish Standing Stones, 6,000 years old
• North Uist’s rare bird habitats and standing stones
• South Uist’s Atlantic beaches and dramatic east coast
• Eriskay and the story of the SS Politician
• Barra’s beach airport and extraordinary coastal scenery

St Kilda and the Wildlife of the Outer Hebrides

If conditions allow, St Kilda is the highlight of the voyage. This volcanic archipelago, lying some 64 kilometres west of the Outer Hebrides, consists of the islands of Hirta, Dun, Soay and Boreray, home to some of the highest sea cliffs in Europe and enormous colonies of puffins, gannets and other seabirds. The archipelago has been uninhabited since 1930, when the last remaining residents were evacuated after millennia of island life. Walking among the abandoned village on Hirta, where several houses have been set up as small exhibitions about the families who lived there, is a quietly moving experience.

St Kilda can only be reached by sea, and the conditions need to be right. Flying Dutchman will make for it whenever the weather allows, and if the Atlantic has other ideas, there is more than enough to see on the sheltered side of the Outer Hebrides.

The waters throughout this voyage are exceptional for wildlife. Puffins, dolphins, basking sharks and whales are all possible sightings, and nights spent at anchor in remote island bays, away from harbours and other boats, bring a stillness that is genuinely hard to find anywhere else.

Traditional Tall Ship Flying Dutchman

Not to be mistaken for the legendary ghost ship, Flying Dutchman very much makes port, spending her summers exploring the west coast of Scotland and the Hebrides. Family owned and operated, she’s traditionally rigged with 480m² of sail area and an experienced crew who know these waters well. Below decks, 11 twin ensuite cabins are warm and comfortable, with all bedding and towels provided.

A dedicated chef makes the most of fresh local Scottish produce throughout, with breakfast and lunch included and evening meals taken ashore to support local communities. Get involved with hoisting sails and navigation, or simply put your feet up and watch the Hebrides go by.

• 22 guest berths | 11 twin ensuite cabins | Half board
• Dedicated chef | breakfast and lunch included
• Evening meals ashore to support local Scottish hospitality
• Well-stocked bar and generous main saloon
• Perfect for solo travellers, couples and older families

[Read more about Flying Dutchman]

Things to note

Sailing vs Shoretime

Nightwatches?

Travel insurance notes

As this is an active adventure holiday, we advise that everyone has the appropriate personal accident travel insurance whilst onboard in addition to standard travel insurance which would cover you in the time between making your booking and departing for your adventure. These policies can sometimes be combined so please check with your travel insurance provider.

Please read more information on our Insurance guidelines page.

This voyage will not be more than 12 miles offshore.