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Tall ship sailing holidays - all over the world

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‘Hands on’ sailing participation is at the core of all Classic Sailing holidays. You don't have to be a sailor. Our skippers help you become the crew on tall ships, barques, brigs, schooners, gaff cutters, luggers and privateers. 

Whether you want an epic sailing expedition or a weekend taster, we can offer expert advice based on 22 years of experience helping customers fulfil their sailing dreams. 11,051 independent travellers and adventure seekers have joined Classic Sailing vessels to explore coasts, islands and oceans worldwide since 1997.



Why did I sail? - Never had before and wanted my first experience to be on a beautiful traditional sail boat. I wasn’t disappointed. Carolyn P June 2019

Latest news

More Open Boat Sailing & Camping Voyages 2021
Small boat sailing, the frisson of finding a wild camping site in coves and creeks is back in 2021

Special offers

RYA Day Skipper Theory Course
RYA Day Skipper Theory - Save £50 on our longer on line courses
Hands on holidays with classic Sailing. Photo Arthur Smeets

Hands on sailing. Learn the ropes with us

You don't need any experience as our professionals will teach you to become the crew on eye catching vessels so you can revel in the glory of sailing them. If you are already hooked on sailing then we have challenges and destinations to keep you busy for a lifetime.

Who Comes?   Is it Right for Me?

All our vessels accept individual bookings. Solo travellers make up the majority of our customers, but our ships take teamwork to set sail, so it’s a great way to meet new people. We have tall ships adapted for disabled crews, vessels that have great accommodation for couples, family friendly options and a huge choice of short tasters for newcomers. 

Our guest crews are all nationalities and ages. There are plenty of female customers, crews and captain's. It is a active sailing holiday where you learn by 'doing.' Language is not a barrier. 

Check out the sailors who are already hooked on Classic Sailing Facebook and become part of our traditional sailing community. 

Agnes pilot cutter sleeps 6

A Traditional Sailing Fleet of 22 Vessels

For us a real sailing boat or sailing ship is one which makes your heart skip a beat as it comes around a headland, or makes a fisherman look up from his nets and smile as you sail past. Classic Sailing only works with beautiful classic boats and tall ships that are traditionally rigged with gaff sails, lug sails and square sails. Sails are set with blocks and tackles and lots of teamwork.

Learn while you sail - Gain new skills on holiday

If you are looking for the perfect place to grow your sailing skills then Classic Sailing offer far more than a conventional RYA Sailing School. We do offer the full range of practical and theory RYA Sailing Courses and qualifications from RYA Competent Crew to  RYA Ocean Yachtmaster but there is so much more you can learn about throughout the Classic Sailing fleet.

Our sailing holidays are rich in learning opportunities like - lugger racing skills, learning about bio-dynamic wine growing on a wine cargo run, marine photography, wildlife or art voyages with experts. The beauty of the longer ocean tall ship voyages is you have time to learn, whether it be square rig skills, oceanographic research or meeting with different cultures from a position of mutual respect.

Download our FREE Tall Ships Guide - Types of tall ship explained in photos, sailors jargon, sail names, how watches are organised and lots of tips to prepare you before you sail in one illustrated book:

 Free Tall Ships Guide

Wizard Pool in the Outer Hebrides on Eda Frandsen

Explore our sailing grounds

Exploring Ashore is Part of the Adventure

Classic Sailing choose the best sailing grounds for awe inspiring coastal scenery, wildlife opportunities and sailing winds. We are excited by mountain backdrops and natural anchorages, self-sufficient local communities, historic ports and remote islands. Destinations range from weekends away in Cornwall and other trips right on your doorstep to hot destinations like the Caribbean or Polynesia. If you prefer icebergs and glaciers then try sailing expeditions in Antarctica or the Arctic.  Maybe your destination is more about relaxing ashore with seafood, wine and music after some memorable sailing, so check out our summer festival and tall ship event voyages.

Boating holidays that make a difference. Deliver organic wine under sail on Grayhound

Not sure what type of voyage? - Inspire me

Classic Sailing have never aimed our activity holidays exclusively at sailors. Since 1997 We have introduced over 10 000 people to sailing and travel under sail. If you are excited by the idea of a sailing holiday but not sure where to start, then have a look at some of our favourite holiday types.  Our 'Inspire Me' pages will give you ideas for every type of voyage.


Classic Sailing

What others say about us


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"A life changing experience with talented crew who gave us hope for mankind ...and biscuits"

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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

Contact Us

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