Good for

  • Cruising
  • Exploration
  • Ocean passages
  • Training
  • Wildlife
  • Winter sun
  • Sun
  • Racing

Duration

  • 2 - 6 days
  • 1 week +
  • 2 weeks +

Scotland & the Hebrides

Explore the rugged seclusion of Scotland's Western Isles, proffering breathtaking views, rare wildlife and excellent sailing, Scotland is one of our favourite destinations.

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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, double hull yacht Zuza, cutter yacht Cherokee, or expedition yacht Narwhal.

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 Small Isles and 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 the Cherokee 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.

Sailing Holidays in Scotland

Sailing from Cornwall to Scotland

Join Pellew as she makes the voyage North to the West coast of Scotland. Sail from Cornwall and experience life on the open water.
  • Vessel: Pellew
  • Where: Cornwall/Scotland
  • Duration: 10 days
  • Date: 2 June 2021

Sailing Expedition to St. Kilda, Scotland

Sail with expedition yacht Zuza to one of the most remote and beautiful parts of the UK for a trip of a lifetime!
  • Vessel: Zuza
  • Where: Scotland
  • Duration: 10 days
  • Date: 7 June 2021

Tall Ship Sailing in the Hebrides

Sail with tall ship Blue Clipper as she journeys from the Gateway of the Isles to explore the beautiful West coast of Scotland.
  • Vessel: Blue Clipper
  • Where: Scotland
  • Duration: 10 days
  • Date: 7 June 2021

Sailing & Exploring the Hebrides

Sail the Hebrides on Pellew as she explores remote anchorages, secluded islands and wonderful wildlife locations.
  • Vessel: Pellew
  • Where: Scotland
  • Duration: 7 days
  • Date: 13 June 2021

Sailing the Hebrides, Isle of Skye & Lochs

Sail with Steady from Oban to Ullapool as she explores the Isle of Skye and the lochs of this beautiful Scottish coastline.
  • Vessel: Steady
  • Where: Scotland
  • Duration: 10 days
  • Date: 17 June 2021

Tall Ship Sailing in the Outer Hebrides

Hoist the sails of this spectacular tall ship and explore the magic that the Small Isles, Skye and the Outer Hebrides have to offer.
  • Vessel: Blue Clipper
  • Where: Scotland
  • Duration: 7 days
  • Date: 18 June 2021

Sailing and exploring the Small Isles

Explore the beauty of the Small Isles on the west coast of Scotland under the sail, with plenty of wildlife spotting opportunities!

  • Vessel: Zuza
  • Where: Scotland
  • Duration: 7 days
  • Date: 19 June 2021

Sailing & Exploring the Hebrides

Sail the Hebrides on Pellew as she explores remote anchorages, secluded islands and wonderful wildlife locations.
  • Vessel: Pellew
  • Where: Scotland
  • Duration: 10 days
  • Date: 21 June 2021

Tall Ship Sailing in the Outer Hebrides

Hoist the sails of this spectacular tall ship and explore the magic that the Small Isles, Skye and the Outer Hebrides have to offer.
  • Vessel: Blue Clipper
  • Where: Scotland
  • Duration: 10 days
  • Date: 26 June 2021

Sail to the Outer Hebrides & Shiants

Explore the Outer Hebrides on the West Coast of Scotland and make the journey to the little known but fascinating Shiant Islands.
  • Vessel: Steady
  • Where: Scotland
  • Duration: 8 days
  • Date: 29 June 2021

Island Hopping in The Hebrides

This voyage will use the wind to sail out into some of the remote Hebridean islands, with the west coast of Scotland offering some of the most spectacular sailing waters around.
  • Vessel: Cherokee
  • Where: Scotland
  • Duration: 9 days
  • Date: 29 June 2021

Sailing & Exploring the Hebrides

Sail the Hebrides on Pellew as she explores remote anchorages, secluded islands and wonderful wildlife locations.
  • Vessel: Pellew
  • Where: Scotland
  • Duration: 10 days
  • Date: 2 July 2021

Tall Ship Sailing in the Outer Hebrides

Hoist the sails of this spectacular tall ship and explore the magic that the Small Isles, Skye and the Outer Hebrides have to offer.
  • Vessel: Blue Clipper
  • Where: Scotland
  • Duration: 9 days
  • Date: 7 July 2021

Sailing Expedition to St. Kilda, Scotland

Sail with expedition yacht Zuza to one of the most remote and beautiful parts of the UK for a trip of a lifetime!
  • Vessel: Zuza
  • Where: Scotland
  • Duration: 10 days
  • Date: 13 July 2021

Sailing & Exploring the Hebrides

Sail the Hebrides on Pellew as she explores remote anchorages, secluded islands and wonderful wildlife locations.
  • Vessel: Pellew
  • Where: Scotland
  • Duration: 7 days
  • Date: 13 July 2021

Sailing to St Kilda

Sail to discover the secrets of St Kilda, a remote archipelago off the West coast of Scotland, shrouded in mystery.
  • Vessel: Blue Clipper
  • Where: Scotland
  • Duration: 13 days
  • Date: 17 July 2021

Sailing from Scotland to Northern Ireland

Join Cherokee as she leaves Oban, past the islands of Arran and Bute and into the Irish Sea where she'll head for Portrush.
  • Vessel: Cherokee
  • Where: Scotland
  • Duration: 9 days
  • Date: 17 July 2021

Sailing the Hebrides, Isle of Skye & Lochs

Sail with Steady from Ullapool to Oban as she explores the Isle of Skye and the lochs of this beautiful Scottish coastline.
  • Vessel: Steady
  • Where: Scotland
  • Duration: 10 days
  • Date: 18 July 2021

Sailing & Exploring the Hebrides

Sail the Hebrides on Pellew as she explores remote anchorages, secluded islands and wonderful wildlife locations.
  • Vessel: Pellew
  • Where: Scotland
  • Duration: 7 days
  • Date: 20 July 2021

Sailing and Exploring the Outer Hebrides

The Inner Hebrides are rich in history, wildlife and unique coastlines. Zuza's crew will take you to the best parts, sharing their knowledge with you.

  • Vessel: Zuza
  • Where: Scotland
  • Duration: 7 days
  • Date: 24 July 2021

Sailing & Island hopping in the Hebrides

Sail with Steady in the West coast of Scotland offering some of the most stunning cruising grounds in the world.
  • Vessel: Steady
  • Where: Scotland
  • Duration: 8 days
  • Date: 30 July 2021

Sailing Expedition to St. Kilda, Scotland

Sail with expedition yacht Zuza to one of the most remote and beautiful parts of the UK for a trip of a lifetime!
  • Vessel: Zuza
  • Where: Scotland
  • Duration: 10 days
  • Date: 2 August 2021

Discovering the Scottish Highlands by Tall Ship

Explore the hidden gems of the Scottish Highlands and surrounding islands under sail on tall ship Blue Clipper.
  • Vessel: Blue Clipper
  • Where: Scotland
  • Duration: 7 days
  • Date: 2 August 2021

Sailing Iona & Staffa

Discover some of the most magical sailing grounds in the Hebrides aboard tall ship Bessie Ellen
  • Vessel: Bessie Ellen
  • Where: Scotland
  • Duration: 7 days
  • Date: 7 August 2021

Discovering the Scottish Highlands by Tall Ship

Explore the hidden gems of the Scottish Highlands and surrounding islands under sail on tall ship Blue Clipper.
  • Vessel: Blue Clipper
  • Where: Scotland
  • Duration: 6 days
  • Date: 10 August 2021

Sailing and exploring the Small Isles

Explore the beauty of the Small Isles on the west coast of Scotland under the sail, with plenty of wildlife spotting opportunities!

  • Vessel: Zuza
  • Where: Scotland
  • Duration: 7 days
  • Date: 14 August 2021

Sailing & Whale Watching in the Hebrides

Explore the majestic island of Mull and her surrounding isles as you keep your eyes peeled for whale sightings while under sail.
  • Vessel: Bessie Ellen
  • Where: Scotland
  • Duration: 7 days
  • Date: 14 August 2021

Discovering the Scottish Highlands by Tall Ship

Explore the hidden gems of the Scottish Highlands and surrounding islands under sail on tall ship Blue Clipper.
  • Vessel: Blue Clipper
  • Where: Scotland
  • Duration: 7 days
  • Date: 17 August 2021

Sailing and Walking in the Hebrides

Enjoy 8 days sailing exploring the Hebrides with yacht Steady as she stops to go ashore and take guided walks among the beautiful Scottish landscapes.
  • Vessel: Steady
  • Where: Scotland
  • Duration: 8 days
  • Date: 17 August 2021

Sailing Weekend exploring Mull

Sail the Hebrides with Zuza, exploring hidden anchorages and amazing landscapes on foot - the perfect time of year for wildlife watching!

  • Vessel: Zuza
  • Where: Scotland
  • Duration: 3 days
  • Date: 21 August 2021

Sailing to St. Kilda, Scotland

Sail to one of the most remote parts of the UK, stroll barefoot on deserted white sands, take the helm and raise the sails for an adventure of a lifetime.
  • Vessel: Bessie Ellen
  • Where: Scotland
  • Duration: 10 days
  • Date: 21 August 2021

Sailing & Exploring the Orkney Islands

Explore the North coast of Scotland and discover the beauty of the Orkney Islands under sail on tall ship Blue Clipper.
  • Vessel: Blue Clipper
  • Where: Scotland
  • Duration: 11 days
  • Date: 25 August 2021

Sailing the Inner and Outer Hebrides

Explore the Inner and the Outer Hebrides for ten days sailing and wildlife watching onboard Steady.
  • Vessel: Steady
  • Where: Scotland
  • Duration: 10 days
  • Date: 27 August 2021

Sailing and exploring the Small Isles

Explore the beauty of the Small Isles on the west coast of Scotland under the sail, with plenty of wildlife spotting opportunities!

  • Vessel: Zuza
  • Where: Scotland
  • Duration: 7 days
  • Date: 2 September 2021

Tall Ship Taster Sailing

Join Blue Clipper as she sails from Aberdeen to Newcastle and takes guests on a 5-day classic sailing experience.
  • Vessel: Blue Clipper
  • Where: Scotland
  • Duration: 5 days
  • Date: 6 September 2021

Sailing from Scotland to Ireland

Sail with Steady from Scotland to Ireland, exploring remote anchorages, traditional harbour towns and two Celtic coastlines.
  • Vessel: Steady
  • Where: Scotland/Ireland
  • Duration: 10 days
  • Date: 8 September 2021

Sailing and Exploring the Outer Hebrides

Sail with Zuza through the Minch of Scotland to the Outer Hebrides exploring history, landscape and beautiful wildlife.
  • Vessel: Zuza
  • Where: Scotland
  • Duration: 7 days
  • Date: 10 September 2021

Trek & Sail in the Hebrides

Join our VentureSail crew and Mammut Mountain guides on a bespoke trek and sail adventure in the Hebrides.
  • Vessel: Zuza
  • Where: Scotland
  • Duration: 4 days
  • Date: 17 September 2021

2022 Sailing from Cornwall to Scotland

Join Pellew as she makes the voyage North to the West coast of Scotland. Sail from Cornwall and experience life on the open water.
  • Vessel: Pellew
  • Where: Cornwall/Scotland
  • Duration: 10 days
  • Date: 23 April 2022

2022 Sailing the Small Isles

Explore the Small Isles of the Hebrides on Pellew as she sails to remote anchorages, secluded islands and wonderful wildlife locations.
  • Vessel: Pellew
  • Where: Scotland
  • Duration: 7 days
  • Date: 4 May 2022

2022 Sailing the Small Isles

Explore the Small Isles of the Hebrides on Pellew as she sails to remote anchorages, secluded islands and wonderful wildlife locations.
  • Vessel: Pellew
  • Where: Scotland
  • Duration: 7 days
  • Date: 28 May 2022

2022 Sailing the Small Isles

Explore the Small Isles of the Hebrides on Pellew as she sails to remote anchorages, secluded islands and wonderful wildlife locations.
  • Vessel: Pellew
  • Where: Scotland
  • Duration: 7 days
  • Date: 15 July 2022

2022 Sailing from Scotland to Cornwall

Join Pellew as she makes the voyage South from the West coast of Scotland to Cornwall.
  • Vessel: Pellew
  • Where: Scotland/Cornwall
  • Duration: 10 days
  • Date: 22 July 2022
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Destinations

Our range of vessels enables us to offer several destinations all over the globe. Which adventure will you choose?

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Tall Ships fleet

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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