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.

More Stories

Tall Ship Sailing on Morgenster with Classic Sailing

24/04 Inspiration

Great Summer Voyages

Great Summer Voyages  Sail the coastal waters of Cornwall, Isles of Scilly, Devon, Scotland, the Baltic, Mediterranean, and Brittany on tall ship voyages ranging

Read More

28/02 Educational

2024 – Classic Sailing’s Year of Skills: Confident Crew

Throughout 2024, we’re shining the spotlight on the various ways our customers get more with a Classic Sailing booking. Sailing on a traditional vessel

Read More
Wild Boy and Leafy

01/02 Boat building

2024: Classic Sailing’s Year of Skills! It’s not just sailing, you know!

Throughout 2024, we’re shining the spotlight on the various ways our customers get more with a Classic Sailing booking. There are many physical and

Read More

14/01 Inspiration

Turning the Tide on Blue Monday

Turning the Tide on Blue Monday Blue Monday, marked on 15th January 2024, is here again. Many of us find ourselves caught in the

Read More
Pilot Cutters in Fowey

21/05 Festivals

Pilot Cutter Review Update 21-05-24

Pilot Cutter Review 2024 Sponsored by H Tiddy Estate Agents of St Mawes Grateful thanks. We are delighted to announce that H Tiddy have come

Read More
Vega Cargo of Hope

17/05 Book Reviews

Cargo of Hope

Voyages of Hope: The Story of Vega The story of the voyages of Vega from 1892 to the present day. This tale concentrates on

Read More
Pilot Cutter fleet leaving Fowey

02/05 Vessel News

Announcing the 18th Annual Classic Sailing Pilot Cutter Review for 2024

Pilot Cutter Review Sailing in Fowey and St Mawes Cornwall  30th May to 2nd June 2024 We are excited to announce that the 18th

Read More