Sailing Holidays in Scotland
Explore the rugged seclusion of Scotland's Western Isles, proffering breathtaking views, rare wildlife and excellent sailing, Scotland is one of our favourite destinations.
Sailing the Outer Hebrides; Isles of Lewis & Harris
- 21 June 2025, 7 days
- Vessel: Zuza
- Port: Oban, Scotland
- Board type: Full Board
Sailing the Caledonian Canal and Great Glen Way
- 20 September 2025, 8 days
- Vessel: Steady
- Port: Oban, Scotland
- Board type: Full Board
Tall Ship Taster Experience in the Hebrides
- 13 June 2025, 4 days
- Vessel: Blue Clipper
- Port: Oban, Scotland
- Board type: Full Board
Adventure Sailing in the Hebrides: Skye and the Small Isles
- 21 July 2025, 11 days
- Vessel: Steady
- Port: Hebrides, Scotland
- Board type: Full Board
Sailing the Shetland Islands and Orkney
- 25 July 2025, 10 days
- Vessel: Flying Dutchman
- Port: Scotland
- Board type: Half Board
Sailing Around the Isle of Skye
- 11 September 2025, 7 days
- Vessel: Stravaigin
- Port: Mallaig, Scotland
- Board type: Full Board
Sail the Caledonian Canal from Inverness to Oban
- 9 September 2025, 6 days
- Vessel: Bessie Ellen
- Port: Scotland
- Board type: Full Board
Sailing in the Outer Hebrides & St Kilda
- 30 July 2025, 10 days
- Vessel: Stravaigin
- Port: Oban, Scotland
- Board type: Full Board
Discover the Inner Hebrides, Jura & Colonsay & Corryvreckan
- 28 August 2025, 7 days
- Vessel: Zuza
- Port: Oban, Scotland
- Board type: Full Board
Offshore Sailing from Amsterdam to Inverness
- 27 March 2025, 10 days
- Vessel: Flying Dutchman
- Port: Amsterdam/Scotland
- Board type: Half Board
Explore Scotland’s bewitching landscape under sail
Boasting more than 10,000 miles of stunning coastline, Scotland and its islands provide something for everyone; a unique land of opportunity, rich with history, wildlife, jaw-dropping beauty and world-leading whiskies.
The sensational Scottish islands (all 750 of them) are considered by many to be the jewel in the crown of Scotland’s immense coastline, with remote islets, secluded sea lochs and sheltered coves, many of which are inaccessible by land.
Whether you want to island-hop, go off-grid, wildlife watch, or gourmet dine, our tailored Scottish sailing holidays in the Hebrides, Orkney, or the Firth of Clyde will ensure memories that last a lifetime.
The Western Isles
Absorb the Hebridean magic aboard the majestic Bessie Ellen, comfy yachts Zuza or Stravaigin, staysail Steady, tall ship Schooner Blue Clipper.
From early summer, the Western Isles bathe in long warm sunny days and are home to ideal sailing conditions. When the wind decides to blow in from the Atlantic, your skipper will know plenty of sheltered bays or long winding lochs to continue your adventures.
From Iona’s white sands to the enchanting isles of Arran, Rum, Staffa, Iona, Jura and Islay, the Sea of the Hebrides beckons to its remote landscapes, historic monuments, local cultures and magical wildlife. Once anchored, there is plenty of time to explore ashore, climb a high point, swim off the boat or explore remote white sandy beaches.
A highlight for wildlife enthusiasts is a visit to the puffin colony, where you will be welcomed among their burrows. Other birds of prey including Buzzards, Kestrels, Sparrowhawks and Peregrines can also be spotted on the beautiful Scottish coastline. Hebrides sailing trips can also offer unforgettable encounters with Common, Bottlenose, Whitebeak and Risso dolphins. There are plenty of whales in this part of the world too; including the resident pod of Orca, many have been lucky enough to see gliding elegantly through the waters.
Watch The Girl Outdoors sailing the Hebrides on Bessie Ellen. Or, for more detailed information on the islands that make up the Inner and Outer Hebrides, take a look at our blogs on Mull and her surrounding Isles, and another on the Sailing to St. Kilda.
The Orkneys
With no fewer than 36 Sites of Special Scientific Interest, 13 Special Protection Areas and 13 RSPB nature reserves, a voyage along the east coast of Scotland aboard is equally unforgettable. You’ll visit authentic fishing villages and working harbours, taking in the history and sights of the island of Rousay, the small atmospheric harbour of Whitehills, and Kirkwall.
Wildlife in the Orkneys is spectacular. You’ll cruise below its towering cliffs, home to over a million seabirds, including puffins, thousands of grey and common seals and an array of marine mammals.
The Firth of Clyde
Protected by the Kintyre peninsula with an archipelago of rugged islands, the Firth of Clyde is a fascinating area of Scotland. With the deepest coastal waters in the British Isles, ancient castles, meandering lochs and an abundance of wildlife, this area is certainly best explored by boat.
The Kyles of Bute is said to be one of the prettiest sailing passages in Britain and, with fjord-like lochs and heather-clad hills, these waters make for perfect sheltered sailing experience.
Destinations
Our range of vessels enables us to offer several destinations all over the globe. Which adventure 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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