Advanced Thrills & Spills, Sailing Challenges & Command Skills

The staff in the Classic Sailing Office have enough sea miles to go around the world 6 times, but we are not embarrassed by paying to go a sailing voyage, if it fits our ambitions. The logical conclusion of a sailing hobby is to buy your own boat, but there are cheaper ways to see the world on a beautiful and probably bigger sailing ship…and keep the day job. 

Experienced sailors don’t always want their next voyage to be more challenging or harder. We have plenty of customers who have weathered the gales and already been tested for courage by the sea. Our office and sea staff hope we can offer you mutual respect and we can learn from each other. When you ring us we are ready to answer questions from novices to master mariners. You might be someone who knows enough to look for an ocean passage that has trade winds in the right direction, but we can tell you which ship might will offer the most advanced thrills or good company.

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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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