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

Gazing into the sea and sky on Tecla

17/01 Inspiration

I never tire

Why my traditional sailing experience never tires me. Adam – Sunday, January 20th 2026 Hi sailor, This week I’m going to tell you all

Read More

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

Read More
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

Read More