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.

More Stories

Mountains by Port Lockroy

18/10 Inspiration

Sailing with Classic Sailing and Trekking with Jagged Globe

Sailing with Classic Sailing and Trekking with Jagged Globe At first glance, sailing across open seas and trekking through Himalayan peaks might seem worlds

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16/10 Educational

When The Long Trick’s Over: How to ‘Park’ A Tall Ship

When you sail on one of the historic or traditionally rigged vessels in our fleet, you’re not just a bystander —you become part of

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Santa Maria Manuela crew out on the bowsprit. experience a relaxed sailing adventure holiday aboard santa maria manuela with classic sailing.

04/10 crew profile

The Role of the Bosun

The Role of a Bosun on a Tall Ship I count myself lucky to have been a tall ship bosun, though I’ll admit it

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Recently Viewed Voyages

Tallulah

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Embark

Tue 08-07-2025

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Disembark

Mon 14-07-2025

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landing on sampson - a pilot cuttersails past

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£1390

Twister

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Embark

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Disembark

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Embark

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Disembark

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Oban, Scotland

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£2300.00