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Sailing Scotland - The best way to see the Western Isles.

Experience the Wonders of Sailing in Scotland

Experience sailing Scotland with some of the finest sailing waters in the country, how better to explore the rarely reached remote areas of the Western Isles or the charms and seclusion of the Inner Hebrides than on a traditional sailing vessel?

Admire the natural beauty of the Western Scotland, with scenery that will simply take your breath away. Rugged coastlines, endless sandy beaches, secluded sea lochs surrounded by mountainous backdrops and ever changing landscapes in the light. Combine this with a wealth of bird and marine life and a temperate maritime climate, a traditional sailing holiday is the finest way to take in your surroundings and experience the sense of getting away from it all.

At Classic Sailing we like mountains and islands as a dramatic backdrop for our sailing voyages. Sailing Scotland, the Western Isles, Inner Hebrides, and sea lochs between the remote mainland peninsulas create thousands of miles of unspoilt coastline. In Western Scotland you can often see ridge after ridge of mountains, fading to a purple haze in the distance. A perfect scene for a water colour painting with fast changing weather systems and an ever changing sky.

Tall Ship Leader - 1892 Brixham Trawler

Leader is back in Scotland for part of the summer.  This legendary charter vessel is an important part of our maritime heritage and now stronger than ever after a major renovation last year replacing decks, deck beams and a new main mast.  A powerhouse under sail and a brilliant floating base to explore the Highlands, Leader also offers some themed voyages like traditional music or mountain walking with a guide. Leader takes 12 guest crew plus her skipper, mate and cook.

Leader - Scotland Sailing Schedule


Agnes - A Pilot Cutter In Scotland

For those of you that miss Lizzie May or Ezra in the Highlands there is help at hand. They are both Luke Powell pilot cutters, and now 46ft Agnes -  the biggest pilot cutter from the Working Sail shipwright, is now heading to Scotland for mid summer 2017. 

Agnes Scotland Sailing Schedule

Irene - 1907 West Country Trading Ketch 

Historic sailing ship Irene was built in 1907 and her elegant lines and authentic rigging will please the artists and romantics in the guest crew. If you prefer exploring on a larger vessel then Irene is 116ft long but only takes 8 guest crews in twin cabins with ensuite facilities. Irene often heads for the Western Isles in the early summer when days are longest. From Oban, Irene can cover quite an extensive area in a week - with the Southern half of the Outer Hebrides possible or to reach as far North as Skye, Canna and Rum. 

Irene’s  voyages in Scotland


Eda Frandsen - Explore the Western Isles  

The Outer Hebrides are very special and the best way to see them in summer is in a decent sized sailing vessel. From Eda's base in Mallaig, the remote Outer Hebrides are a just a few hours sail away. Stable and striking, Eda has sailed these waters for 15 years so knows the best secluded anchorages and unique areas to visit that cannot be reached other than by boat. Explore the spectacular Shiant Islands rich in bird life, or further south to the beautiful islands of Mingulay or Vatesay.  Close by, visit the Small Isles of Rum, Canna, Muck and Eigg where the eagles play, or the stunning lochs and anchorages of Skye where then mountains meet the sea.

The islands are rich in seabirds and the waters surrounding the Hebrides offer high chances of spotting whales, dolphins and seals.

Eda Frandsen Sailing Scotland Schedules

The chances of reaching the remote archipelago of St Kilda rely on a good weather window to visit the remote island of St Kilda, but really that would be the 'icing on the cake' as the Outer Hebrides are worth a 9 day sailing adventure in their own right visiting sparsely inhabited islands, tiny fishing villages, deep lochs and rugged cliffs.


Tecla is now a regular visitor to NW Scotland and St Kilda 

This tough tall ship has sailed right around the world including Cape Horn and now she is fully part of the Classic Sailing fleet, after proving herself to be a sea worthy vessel, with a professional crew, offering fantastic sailing holidays.

She has been adopted by Ullapool as her favourite base for exploring NW Scotland, Outer Hebrides and beyond, but she always producings a bold programme.

In 2016 her multi national crew used Scotland as a launch pad for a Viking type route to Iceland via Orkneys, Shetland, Faroes and Fair Isle.  In 2017 she will be off to Iceland again, as well as 2 longer expeditions to Greenland.

Tecla voyages in Scotland

Tecla full summer programme and Arctic expeditions 

Bessie Ellen - Extensive wild playground

Self sufficent 116ft wooden tall ship Bessie Ellen is a great summer expedition ship for those of you who prefer a larger vessel with a sense of history.  With only 12 guest crew on board you will get plenty of hands on sailing.  Bessie Ellen regularly heads for the Western Isles in the early summer and stays for the long days of summer. From Oban, Bessie Ellen can cover quite an extensive area in a week - with the Southern half of the Outer Hebrides possible or to reach as far North as Skye, Canna and Rum. 

Bessie Ellen in Scotland Sailing Schedule - descriptions, dates and prices

Classic Sailing director Debbie spent 11 days on Bessie Ellen exploring the Outer and Inner Hebrides.

Read her voyage blog and photo diary with everything from Sea Eagles to wild swimming in Fingals cave

Short Sailing Breaks in Scotland

We run a small number of weekend and mid week short breaks in Scotland. Irene, Bessie Ellen and Leader from Oban.

Short Sailing Voyages in Scotland


Adventure Voyages in Scotland.

Our longer voyages in Scotland are normally heading for St Kilda or running the up or down the whole Western Isles.

Longer voyages in Scotland


Weather - Flat water blasts, long mid summer days & a few heatwaves

Scotland frequently offers warm sunny days and great sailing conditions. However, at times like anywhere it can be very windy and the gales come in fast off the Atlantic at any time of year, but the beauty here is you can usually keep on sailing between the islands. There are many miles where Eda Frandsen, Leader, Irene or Bessie Ellen 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. 

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 beachcomb 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.

Anchorage to Anchorage - Self Sufficient Travel

The choice of anchorages is endless on a sailing holiday in Scotland. The energetic can climb to the highest point ashore and look down on your boat in splendid isolation in perfect natural anchorages that south coast sailors can only dream of. 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.

 "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!"


more on Firth of Clyde as a sailing destination

more on the Inner Hebrides - Skye, Mull & the Small Isles

more Oban Southwards - Mull, Colonsay, Islay & Jura

more on the Outer Hebrides  as a sailing destination

more on the Shetlands and Orkneys 


Bessie Ellen anchored in the Shiant Islands with Puffin audience

Sail in Scotland on Eda Frandsen

swimming in Iona Sound with Bessie Ellen crew

Tecla in Loch Scavaig





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