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Mountains, Rich Seas and Abundant Wildlife

Scotland offers you some of the finest sailing waters in the UK and how better to explore the rarely reached remote areas of the Western Isles or the charms of the Inner Hebrides than on a traditional sailing vessel? Our skippers will be your wildlife and cultural guides, teach you to sail, and inspire you to make the most of your active holiday on board and ashore.  These are fantastic voyages if you love mountains and rugged coasts and want to see Scotland through the eyes of a sailor, get close to wildlife and reach some of the most inaccessible wilderness areas in Britain by boat.

Classic Sailing has a wonderful choice of skippered and fully catered sailing holidays that sail in the Scottish waters. Our traditionally rigged boats, schooners and tall ships roam from St Kilda to Shetland, Skye to Islay. Many voyages are themed and beginners will enjoy shorter breaks exploring the islands whilst more experienced sailors may enjoy the challenging expeditions to St Kilda or the Faroes.  

Sailing holidays in Scotland


Puffins by Melissa Williams

Wind Conditions – Flat Water Blasts.

Scotland frequently offers warm sunny days and great sailing conditions. At times Scotland can be very windy and the gales can come in fast off the Atlantic at any time of year. The secret ace that sailing in Scotland has over sailing in other Atlantic facing shores like Cornwall or Ireland is the protecting influence of the island chains. The Inner and Outer Hebrides and the tall mountains give you options to find flat seas and sheltered anchorages from almost any wind direction. There are many miles where our tough sailing ships can escape the ocean swell and go for an awesome flat water blast. Not everywhere is protected, but at least there are safe havens where you can go to reef down and reduce sail so you can tackle the next exposed headland or firth. 

Irene amongst the Scottish Mountains

Long Mid Summer Days 

In June the sun sets very late in the evening so Scottish midsummer days are long. When a high pressure system sits over Scotland you can find yourself in a heatwave with waters so still the mountains and blue skies create a mirror image. The warm Gulf Stream means you can swim off the boat or beach-comb on white quartz sand beaches with no other sunbathers in sight. When a depression sweeps in – boy can it rain, but when the weather front clears the views are crystal clear.

Midge FREE Scotland

A Boat as your Bothy – Sailing and Walking

 Sailing in the Western Isles of Scotland is one of the best ways of exploring these remote islands. You do not have to worry about accommodation, it’s close to nature but cosier than camping!

The choice of anchorages is endless on a sailing holiday in Scotland and your ‘restaurant’ and home comes with you. The energetic can climb to the highest point ashore and look down on your boat alone in perfect natural anchorages that south coast sailors can only dream of. If you prefer solitude to wander the edge of the loch looking for otters, or sketch the landscape then our skippers can generally suggest shorter walks or perfect beaches near to your landing spot. The best bit of the day if often swapping stories from each others forays ashore. Self sufficient aboard your floating home; you can relax snugly in the saloon and wait for supper with an appetite as large as the hills.

Tecla skipper on a high summit in the Faroes

Which ship for my adventure?

If your heart is already set on Scotland as a cruising ground, then your next choice might be ‘Which vessel?’

Maybe and Blue Clipper love to explore the western Ilses of Scotland.  Maybe is a wooden gaff ketch popular with young people but takes all ages, often sailing around the Firth of Clyde. Blue Cli[per has two person cabins and is offering high standards of catering for her voyages in Scotland.

Tecla and Oosterschelde are Dutch tall ships that have sailed the world, and often visit Scotland on the way to more far flung destinations. 

Tecla has made Ullapool her favourite Scottish home port, as it has easy access North of Skye to the Shiant Isles, Outer Hebrides and St Kilda.  She spends time in the Hebrides in the Spring, when there is still snow on the Highland summits on the way to Iceland and Greenland.  

Oosterschelde is a large three masted topsail schooner with elegant below decks accommodation including a piano and spends some time in Scotland most years.


Sailing holidays in Scotland Sailing Voyages


Discover the Faroes, Shetland and Orkney TC051025


Sun 05-10-2025

Reykjavik, Iceland


Wed 29-10-2025

Harlingen, The Netherlands

sail tecla in rhe faroe isles




Iceland-Faroes-Shetland-Orkney-Hebrides TC220924


Sun 22-09-2024

Reykjavik, Iceland


Mon 14-10-2024

Ullapool, Scotland

sail tecla in rhe faroe isles