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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01/01 Classic sailing at 30

Our Theme for 2026 is ‘CLASSIC SAILING at 30’

Celebrating 30 years of Classic Sailing 1996-2026 Last year we celebrated the PEOPLE that bring your sailing voyages to you, and the fascinating range

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Why we recommend DialaFlight to get you thee and back.

31/12 FAQ - Frequently Asked Questions

Why Use a Travel Agent for Flights to Your Sailing Holiday

Travel agent for flights! Surely that’s a bit old-fashioned in our digital age, but when you’re planning a sailing holiday with Classic Sailing, having

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When you love sailing all aspects of sail handling become interesting

28/12 Inspiration

Why We Love Traditional Sailing: A Love Letter to Life at Sea

Hi Sailor, Jessie here,  2025 was the first year in my adult life that I haven’t been sailing. I find this quite a depressing

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