Announcing New Voyages

Sail Scotland 2024

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.

And Much Less than you would imagine – Midge FREE SAILING in Scotland

Provident reputation gathers strength.

It’s excellent news that Provident has completed a successful session in Scotland. The commendable effort from Morag and Steve in prepping the vessel clearly paid off. Scottish waters can be a challenging playground, but a well-prepared ship and crew make all the difference.

The fact that long-time Provident enthusiasts have returned and found the experience even better than before is a significant endorsement. There’s something inherently compelling about Provident, a quality that invites sailors back on board. In a maritime world full of fleeting novelties, that kind of loyalty is its own reward.

‘Fantastic trip. Crew were so keen to help and teach. They clearly loved sailing. Food was outstanding. Restaurant standard. Learnt so much. Had so much fun. Fellow passengers were so friendly. The Highlands and islands were stunning. Would highly recommend.’ Tracy

‘An amazing week! The accommodation was much better than ‘good’ – very cosy and comfy bunks and even electric heads and a great shower – luxury! Fantastic sailing in stunning scenery and lots of birds and wildlife, including eagles and dolphins. The food was excellent and plentiful, always delectable aromas from the galley. All in all, an unforgettable experience on a beautifully restored vessel.’ Elaine

St Kilda 2024

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.

Reality Check

Sailing to St Kilda maybe a destination that some voyages may wish to visit but due to its remoteness this is not always desirable. There are so many wonderful places to go in the Western Isles of Scotland that it is far better to approach the voyage as ‘lets sail to wherever the wind favours‘ and that way you are assured of a fantastic voyage.

Provident Voyages in Scotland

Enjoy Island Hopping in the Orkney, Fair Isles and 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.

Superb sailing and fascinating explorations ashore.

Adam sailed on Trinovante in Orkney, Fair Isle and Shetlands in 2023 and it was everything I could wish for. Su and John run a great ship. We sailed off the quay in Kirkwall after a thorough safety and training session within two hours of joining, no engine was needed. Visited tons of islands and met some characterful locals.

Read Adam’s articles on Orkney and Fair Isle and Shetlands by Sail

Trinovante Voyages in Orkney, Fair Isles and Shetland

Grayhound in Scotland

This summer, cast off aboard the Cornish lugger Grayhound for a series of voyages exploring Scotland’s captivating Inner and Western Isles. Start from Troon, navigating through Arran, Jura, and Islay, and finish up in Oban. From there, set course for the breathtaking Western Isles, finally looping back from a Mallaig departure to the mythical Isle of Skye, with its awe-inspiring Cuillin Ridge. These are no mere jaunts; they’re hands-on sailing experiences through some of the UK’s most scenic waters, offering you the chance to master a traditional Cornish lugger in splendid company. It’s Scotland’s maritime majesty, paired with the allure of hands-on seamanship.

Grayhound in Scotland

Sail on Tecla: 2024

The Tecla, a globe-trotting ship with its roots in Den Helder, Holland, considers Ullapool in Scotland something of a second home. About twice a year, this remarkable vessel graces the port of Ullapool, making it the closest thing to a homecoming outside its Dutch base. Arriving from the temperate climes of Horta in the Azores, the Tecla uses Ullapool as a springboard for its next grand expeditions—destinations that include the chillier latitudes of Reykjavik, Iceland, as well as the sun-drenched Santa Cruz in Tenerife.

These aren’t your run-of-the-mill cruises; they’re proper sailing odysseys that capture the imagination. Take the Ullapool to Reykjavik journey, for example. Before pointing the bow towards the Arctic circle, this voyage first weaves through the poetic landscapes of the Hebrides, Orkney, Fair Isle, and Shetland. It’s like a maritime tapestry, each island a unique stitch in a broader design. From there, the adventure continues to the far-flung Faroe Islands before culminating in the austere beauty of Iceland.

Each of these voyages offers ample time to not just travel, but to truly explore—both the world around you and perhaps a bit of your own character. It’s not just about getting from point A to B; it’s about the stories you collect along the way. And if you ask any seasoned sailor, those are the true treasures of the sea.

Tecla in Scotland 2024

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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