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First Sailing Holidays for Beginners

Want to Learn to Sail?  We believe in ‘learning by doing’, so even if you come purely for a holiday, you will learn new skills effortlessly, as part of the process of going sailing and living at sea. 

If you are a complete beginner, a dinghy sailor who wants to try live-aboard cruising  or a newcomer to boats with bowsprits, then we have a huge choice of day sails, taster weekends, Royal Yachting Association (RYA) courses, or weeks away exploring amazing destinations. Leap into a Caribbean island hopping voyage and we will train you to be adventure crew as soon as you arrive, or go for the structured learning of a RYA sailing course.

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Excited to Try Your First Sailing Experience?

  • We have introduced over 10 000 people to sailing since 1997
  • Most people come on their own
  • All vessels have qualified, dedicated skippers
  • You don't have to start with a RYA Course (but we do run beginners RYA courses called Competent Crew)
  • No barriers to adventure - beginners can sign up for any length of voyage or destination
  • All our voyages include sailing instruction
  • Safety equipment, lifejackets etc are all provided
  • Most our vessels provide sailing waterproofs

Practical and 'Hands On' Sailing - Guaranteed

Our ethos across the whole fleet is 'hands-on' sailing.

All our voyages are sailing courses, with training as an integral part of the experience, because 'you are the crew'.  If you want a sailing adventure where you are a needed and valuable member of a team, whatever your age or ability, then chose Classic Sailing.

On our smaller vessels, the skipper may be the only professional on board, so you will learn every aspect of being a sailor, from how to ‘hand, reef and steer’ to identifying navigational features, or your role in helping to save lives in an emergency. On our tall ships there are more staff to train you, so you will still get plenty of individual attention.

Where are we going then? Chart plotter on 1895 sailing trawler Pilgrim
Where are we going then? Chart plotter on 1895 sailing trawler Pilgrim

Sailing for All - No Experience Needed

Classic Sailing has never aimed our activity holidays exclusively at sailors. Since 1997 we have introduced thousands of people to sailing and travel under sail.

Our skippers will teach you to sail, and we will teach you very well, because we can't go anywhere without you. You are the crew and on traditionally rigged vessels it is all about teamwork, so don't worry about whether you are tall enough, strong enough, agile enough as there are important jobs for all abilities. Like any new outdoor sport or adventure activity there is a lot of jargon to learn, but even on a three day voyage you will leave feeling and sounding like a sailor.



Shared Accommodation

Traditional sailing vessels are not spacious and the majority of accommodation is in shared accommodation cabins of four or more people.

Some vessels have two-berth cabins which are normally reserved for two people travelling together and are more expensive than larger shared cabins.

Solo Majority

Most of our sailors travel as solo travellers and shared accommodation is both more economical and secure.

Shared cabins are always the same gender.


The beauty of sharing a cabin of four or more people is the security it offers. It would feel more insecure to share with one other person in a closed cabin, even though they are of the same gender. 


If you prefer total privacy two-berth cabins may be available for single occupancy at an additional charge. If the voyage you are interested in offers two-person cabins please contact us to ask about availability and price of single occupancy.

RYA courses on classic boats like Golden Vanity and Moosk

Learn the Ropes with a RYA Sailing Course

A more structured and intensive way to learn to sail, or progress your skills, is to book on a RYA course. Our RYA teaching boats are all wooden classic boats  AND if you complete the syllabus successfully, you will gain a RYA Certificate that is relevant for modern yachts, classic boats or tall ships.

The Royal Yachting Association (RYA) is the sailing national body in the UK. The RYA have courses for every sort of sailing from windsurfing and dinghies to sailing on bigger yachts (cruising).  Classic Sailing has been a recognised RYA Training Centre for over 15 years offering the full range of cruising courses where you live on board.

RYA Competent Crew is the beginners course for complete novices, but equally suitable for anyone who has maybe tried yachting with friends but wants a more solid base of seamanship skills to feel confident as crew. Equally it would suit a dinghy sailor wanting to try larger boats. The principles of tacking, 'steering a boat to windward' or adjusting the sail angle for maximum sailing efficiency are the same on all sizes of sailing boat, but there are new things to learn in the crossover from dinghies to 40ft sailing boats. We also have quite a few Classic Sailing customers who have tried a tall ship first and now want to learn small boat handling.

More about our RYA Competent Crew Courses


Richest Variety of 'sailing courses' & learning at sea under one roof.

If you are looking for the perfect organisation to grow your sailing skills over a number of years then Classic Sailing offers far more than a conventional RYA sailing school. Yes we are a RYA recognised training centre, but we are passionate about sailing and the sea in the widest sense. The company ethos has always been more than just learning to sail  – appreciating wildlife, conserving maritime heritage, promoting green ways of travelling, and connecting with seafaring communities is a strong part of what we do.

We do offer 6 day RYA sailing courses which follow a nationally recognised syllabus (see below), but if you want something a bit different we have sailing courses, without a formal certificate. They are rich in learning opportunities and range from day sails to round the world epics. If you want to impress your friends with your holiday photos -all our sailing courses are on eye catching classic boats and tall ships. Let us help you fit a voyage to match your free time, learning goals and aspirations.

"Amazing – I never thought I would enjoy it so much! I’m booking another one!" Sarah Edwards

Beginners can sail square riggers too
Beginners can sail square riggers too

There are many ways to learn to sail - Try a Weekend Voyage

The best way to see if you like sailing on the sea and living on a boat overnight is to try one of our short breaks and learn sailing by 'doing it' - with informal instruction from our skippers. We have plenty of 2-4 day tasters on all size of vessel but the smaller ones are best to learn to sail. Golden Vanity Agnes, or Eda Frandsen offer sailing on gaff cutters with only one mast where you will be part of a guest crew of 5-8 people so you will be very involved is every aspect of sailing the boat. These voyages involve lots of short hops along the coast, with sheltered anchorages, ports or moorings overnight.Slightly larger ships like Grayhound, Maybe, Provident and Leader are sail training vessels dedicated to teaching sailing skills on every voyage.

You are unlikely to be the only person who has never steered with a tiller or a wheel, looked at a navigation chart or trimmed a sail to the correct wind angle. Our skippers are very patient and fully appreciate what a strange environment it can be to step onto a moving vessel or sleep in a bunk in a cosy but communal cabin with people you have only just met. The arrival brief and training that you will receive in the first few hours is as much about the domestics and getting used to your new home, as it is about sailing skills. Then you are off to sail to a new destination, picking up skills as they are needed.


Short Breaks and tasters


Hauling together on Grayhound
Hauling together on Grayhound

Not Sure if a Sailing Holiday is for you ?

See our Frequently Asked Questions FAQ or just give us a ring. In the office we have all taught sailing as RYA instructors and charter skippers so we have heard almost every possible question that newcomers to sailing might ask!  Tel 0044 (0)1872 580022

Ambitious Beginners - In a the Deep End types

As full training is always given, there is nothing to stop you trying a longer voyage, but some are tougher than others so we recommend you talk to us first so you are fully aware of what might be involved. (The only voyages that specifically require previous sailing are RYA Day Skipper Courses or higher.)

We have destinations as far afield as Antarctica, Cuba, Cape Verde, Central America, Greenland, Norway and occasionally have ships going all the way around the world.

See our destinations menu for some of the places you can explore on a good looking historic ship or wooden classic boat, or check out INSPIRE ME section for the different types of voyages we offer.





Scorseby Sound in Greenland flat water and great for adventurous beginners
Scorseby Sound in Greenland flat water and great for adventurous beginners
Sailing experiences you might like
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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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