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Weekends & 2-5 Day Sailing Breaks

A long weekend away in the fresh sea air is a fantastic tonic. Our short voyages include accommodation on board, all your meals, sailing instruction and a skipper as your local guide. You can even travel to your joining port by public transport and leave your car behind. Whether you are an experienced sailor 're-charging your batteries' or a newcomer to sailing just treating yourself to a hobby you have always wanted to try, our skippered charter vessels are run by friendly crews who will get you hooked.

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Inspire me more

Sailing Breaks:  A great selection of 1- 5 day voyages

Any day sail, weekend break or 3-5 day short voyage on our traditional boats and tall ships make an ideal taster experience for beginners. If it’s your first voyage you will not be expected to understand all that goes on immediately.  There is full training throughout the voyage but as guest crew you are learning by doing - so its fun and you hardly notice the steep learning curve. In no time at all you will be pulling on ropes and taking an active part in all the sailing as if you had been sailing for years. Classic Sailing currently offer more short breaks on classic boats and tall ships than any other UK traditional boat operator so we hope our website will be your first port of call whenever you want to escape 21st Century life ashore.

Helming by big ships wheel is a bit different from a tiller or a yacht wheel
Helming by big ships wheel is a bit different from a tiller or a yacht wheel

Yacht Sailor? Try something different

Experienced yachtswomen and men regularly come for a refreshing sailing break on our classic boats. It is a great pose to 'own a classic boat' for a few days. Not only are they fun and physical to sail, our gaff cutters, yawls and pilot cutters are all rather show stopping when they come into port, and it is nice to get admiring looks out on the water. Many of our customers come just to experience gaff rig sailing as a change from modern yachts. If you love small boat handling on yachts in the 38ft to 46ft size range then check out Moosk, Golden Vanity, Agnes and Pegasus.

It is also rather satisfying to be crew on something larger than your average ocean going yacht.  In size order we have short breaks on impressive 56ft gaff cutter Eda Frandsen and then getting bigger, three masted lugger Grayhound, Brixham Sailing Trawlers Provident, Pilgrim and Leader and on East Coast trawler Excelsior. Bigger still is 1907 West Country trading ship Irene and Gaff Ketch Maybe. All these ships a originals or wooden replicas with loads of character and no more than 12 guest crew, so everyone feels part of the action and able to approach the skippers and professional crew easily to learn new skills.

See our Fleet 


Sweating and tailing on Grayhound is better than going down the gym
Sweating and tailing on Grayhound is better than going down the gym

A Sailing Break Near You

We have good looking sailing vessels strategically based in the best sailing areas around the UK - Devon and Cornwall, Western Scotland, The Solent, and Northern Ireland.Each sailing ground has a great mix of exciting coastal sailing and more sheltered tidal waters to explore. We work several Dutch ships which have short breaks in Holland, Germany or Belgium and sometimes the Baltic. 

Devon & Cornwall     Scotland     Ireland  Europe (mainland)


Weekend treat? Pilot cutters at play in Cornwall
Weekend treat? Pilot cutters at play in Cornwall

Try Something Alternative for the Weekend - All Inclusive 

The beauty of our short breaks is that we provide a mini adventure in an unusual environment with so many experiences thrown in that they always feel like you have been away for more than a few days. All you need to do is book and turn up with enough clothing for an active outdoor weekend and a sleeping bag. We provide accommodation on board, waterproofs if you need them, 3 freshly cooked meals (special diets catered for), full instruction and a sailors view of our local coastline, wildlife and maritime history. You provide the human power and teamwork to sail our inspiring vessels to the next destination under sail. The planet will thank you too for leaving the car behind for a few days.

Weekend Voyages


learn to sail a sailing lugger
learn to sail a sailing lugger

Short Voyages on a Tall Ship in Europe

For a more authentic experience of life at sea on a proper large sailing ship you need to spend a night or two aboard, climb aloft to work the sails, experience an anchor watch or steer a sailing ship under the stars. We never seem to have enough short sailing breaks and weekends around the British Coast, so you do need to sign up early. You can become the crew on a tall ship for 2-4 days, sailing the coastline of Britain and often an overnight passage to a port in France, Ireland, Belgium or the Netherlands.

Short Voyages on a tall ship


Tall Ship Breaks on Brig Morgenster
Tall Ship Breaks on Brig Morgenster. photo by Mikael Malmberg
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Why book with Classic Sailing?

The call of the sea

Destinations for sailors & explorers

Over 300 voyages a year

11, 051 customers introduced to

traditional boats and tall ships.

Tell us your sailing dreams


Office Team of Skippers

6 Times Around the World between Us

Selling Holidays for 22 Years

2 Dogs to make us laugh

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