Announcing New Voyages

Sail Scotland 2023

Explore Scotland’s wilderness and wildlife on a traditional sailing adventure!

Join a traditional sailing vessel, no sailing experience required. Our skilled skippers will guide you through wildlife encounters and teach you the art of sailing, allowing you to immerse yourself in Scotland’s breathtaking beauty. With sailing, you can get up close to nature and reach inaccessible wilderness areas that are only reachable by boat.

No Experience required.

Classic Sailing offers “hands-on” sailing holidays in Scotland, and no prior experience is required. Whether you’re a beginner looking to explore the islands or an experienced sailor seeking challenging expeditions, we have the perfect voyage for you. Sail to St Kilda, Orkney, Shetlands or Skye, Islay and tons of other islands on our fleet of traditional boats.

Don’t miss this opportunity to create lifelong memories and uncover the wonders of Scotland’s coastline. Start planning your dream sailing holiday now!

All Voyages in Scotland


Much and More

There are so many voyages and so much to see in Scotland we can only show a small selection here.

St Kilda 2023

St Kilda is a remarkable archipelago located in the North Atlantic Ocean. Though the last inhabitants left almost 100 years ago, it is now home to nearly 1 million seabirds, including the UK’s largest colony of Atlantic puffins. Recognized as a UNESCO World Heritage site for its natural and cultural significance, St Kilda offers a unique experience.

Caring for St Kilda by the National Trust for Scotland.

Leader LD150623 Start and finish in Mallaig, Thursday 15th to Thursday 22nd June, £1240 per person

Enjoy Island Hopping in the Shetlands:

Discover the beauty of the Shetland Islands through a sailing adventure. With seven days at your disposal, our skipper and crew aboard the Trinovante will plan the itinerary to make the most of the conditions. Thanks to the long summer days, you’ll have ample daylight for exploration. This trip offers a delightful mix of onshore adventures and incredible island-hopping sailing opportunities.

Trinovante TR110723 Start and finish in Lerwick, Tuesday 11th to Tuesday 18th July, £1295 per person

Tenacious Clyde Day Sail:

If you’re looking for a one-day Tall Ship sailing experience, join us for a Tenacious Day Sail. This is the perfect opportunity to get a taste of life on board a Tall Ship. Sail in the Lower Clyde while taking in the magnificent scenery and enjoying a memorable adventure.

Tenacious TNSDS150723 Start and finish in Greenock, Saturday 15th July

Tall Ships Race 2023 – Morgenster:

Embark on an amazing voyage aboard the Morgenster, starting from Fredrikstadt, Norway, and heading to Lerwick in the Shetlands. This journey is open to participants over the age of 18. Cruise alongside other traditional sailing ships, engage in friendly racing, and experience the awe-inspiring nature of life at sea. The exciting racing conditions will challenge your skills and offer opportunities to learn something new.
Morgenster Fredrikstad to Lerwick, Monday 17th to Friday 28th July, €1320

Grayhound the Big One:

Join on a seagoing adventure with Grayhound, sailing around the Top of Scotland from the Minch to Inverness via Orkney. This voyage takes you along the homeward path of the Vikings, offering a thrilling experience with potentially challenging weather conditions. Grayhound and its professional crew will navigate the seas with ease, allowing you to enjoy the thrill of sailing a ship in its element.

Grayhound GR310823 Ullapool to Inverness via Orkney, Thursday 31st August to Sunday 10th September, £2165

Sail on Tecla: 2024

Tecla offers an extraordinary sailing experience in Scotland, combining wildlife, culture, history, and remoteness. Scotland’s mountains, rich seas, and abundant wildlife await you as you explore the rarely reached remote areas of the Western Isles, Orkney, Shetland and possibly the Fair Isles on the way to Iceland via the Faroes.

Tecla TC190623, Ullapool to Reykjavik, Wednesday 19th June 2024 to Wednesday 10th July 2024, €5170

Sail from Scotland to Devon 2024 – Provident’s Centenary Voyage,

Travel the length of Britain on this historic voyage as Provident sails on her journey “home” for her centenary celebrations in Brixham! With her iconic green hull and stunning red sails, Provident is a very eye-catching vessel. She will be joining other historic Brixham trawlers for an epic regatta.

Provident PR120524 Oban to Brixham, Sunday 12th to Wednesday 22nd May 2024 £1200

Guided by professionals
Our skippers will serve as your guides, teaching you to sail and helping you make the most of your active holiday on board and ashore. These voyages are ideal for those who love mountains, rugged coasts, wildlife, and want to explore Scotland through the eyes of a sailor while reaching inaccessible wilderness areas.

Articles on Scotland
The Hebrides comprises hundred of islands this is an introduction here.
Skye has the longest coastline of any UK island and much of it is only accessible from the sea. Read all about it here.

Sailing in Scotland
Holidays on the Water in Scotland
Scotland – Wildlife on the Atlantic Edge
St Kilda an Introduction

Useful Articles
My First Voyage
What to pack for a sailing holiday
Top Tips on making travel more eco-friendly

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