Sailing holidays in Devon, Cornwall and the Isles of Scilly


Magical Coastline

The West Country has a very long beautiful coastline with many Areas of Outstanding Natural Beauty (AONB) the joy of which is best experienced from a sailing boat.

No Overcrowding at sea – No Airport Queues

Every summer millions of people visit the South West and get stuck on the land with frustrating roads. No crush at sea, we have plenty of room and the biggest open highway there is. 

Sailing boats can go where they want. There are no traffic jams, no parking problems and we take our food and accommodation with us.

It’s a simple, highly relaxing, very special holiday you will want to repeat time and time again.

Ten Reasons Sailing Holidays are Excellent value for money

1. You know all your costs in advance. You may run up a bar bill but that is your decision.

2. Prices include all your meals

3. Your accommodation is included

4. All the safety kit is provided for you

5. Morning and afternoon refreshments are included

6. You get excellent personal attention

7. You are trained in all activities onboard by the professional crew.

8. Your money is helping maintain the traditional sailing industry

9. You meet new people without having to provide hospitality

10. You are benefiting your health see our article “Is the Sea Good for the Soul”.

Big selection of unique voyages to please all levels of sailing experience.

  1. Over 100 voyages to choose from in Devon, Cornwall and the Isles of Scilly
  2. Day Sails in Devon and Cornwall, morning, afternoon and evening cruises.
  3. Wild swimming voyages.
  4. Yoga and boot camp trips.
  5. Short Breaks, mid week and long weekend breaks
  6. Festivals in Falmouth, St Mawes, Mousehole and Brixham
  7. Adventure sailing holidays to the Isles of Scilly, the subtropical British Paradise.
  8. Traditional Sailing Skills courses
  9. RYA Courses for Competent Crew
  10. RYA Day Skipper Practical and Theory Courses
  11. RYA YachtMaster Preparation Course

No Experience Needed – Not Just for Sailors

“Let’s Try Sailing”

Classic Sailing has never aimed our activity holidays exclusively at sailors. 

Since 1997 we have introduced thousands of people to sailing. 

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, or agile enough as there are important jobs for all abilities. 

Top Tips for your first sailing trip.

“If you can dream it, you can do it.” Walt Disney

  1. Choose a short voyage
  2. You trip should be as close to you as practical
  3. No sailing experience of any sort is required
  4. Remember, everyone has had a first voyage.
  5. The ship you sail on wants you to be a regular sailor.
  6. There is no need to buy expensive sailing kit.
  7. All our vessels are commercially licensed to ensure your safety.
  8. All safety kit is provided on board.
  9. A list of what to take with you is part of all voyage details
  10. Solo travellers never share cabins with the opposite gender.
Voyages for your first sailing trip


More Stories

Tall Ships by Max Mudie at

15/06 Announcing New Voyages

2023 Sailing Schedules

First to hear will be our Newsletter subscribers. More Schedules being added. Oosterschelde 2022- 2025 Mascotte 2023 Morgenster 2022 – 2023 Tallulah 2022 –

Read More
refit Work on Oosterschelde

23/09 Darwin200 Around the World

Oosterschelde September 2022 Maintenance

. MAINTENANCE  Major job, After two previous restorations of a part of the hull, we decided to tackle the third part as well. This

Read More

22/09 Announcing New Voyages

Wow – Pilgrim gets around in 2023

. Historic Brixham Sailing Trawler Pilgrim has an exciting program for 2023.  Half Day Want a mini adventure for you and the family? Take

Read More
Sailing on Anny of Charlestown with Classic Sailing


Sea, Songs and Sailing

Join some of the superstars of the UK folk scene as they set sail along the south coast of Cornwall. Anny of Charlestown is

Read More