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Classic Sailing is run by Professional Sailors to give you the best sailing holiday advice.

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Featured Journal

06/05 Educational

Nine Great Ways to Explore the Coast

1 Sailing 2 Sea Kayaking 3 Coasteering 4 Cliff climbing 5 Walking 6 Cycling 7 Horse riding 8 Wild Swimming 9 Rowing + Best

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Pilot Cutter Review 2022 (Number 16)

20/04 Inspiration

Sailing holidays in Devon, Cornwall and the Isles of Scilly

  Magical Coastline The West Country has a very long beautiful coastline with many Areas of Outstanding Natural Beauty (AONB) the joy of which

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Sailing on Anny of Charlestown with Classic Sailing

20/04 No Experience required

Day sailing in Devon and Cornwall

No sailing experience required. Trips from £59 in Devon HALF DAY SAILING TRIPS IN DEVONSail from Brixham in the morning with tea or coffee

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18/04 Announcing New Voyages

Wild Swimming in Cornwall from a sailing ship

Wild Swimming in Cornwall from Tallulah with safety supervision. Swimming from Tallulah in a beautiful anchorage is often a big part of the fun

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Wild Boy built by Debbie, Tallulah's skipper.

02/04 Educational

Conserving our maritime heritage

At Classic Sailing we still believe the best way to conserve our maritime heritage and traditional sailing skills is for historic vessels to go

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Classic Sailing

24/03 Inspiration

Twelve Reasons Sailing Holidays are Great Value

12 Reasons Sailing Holidays are Great Value. All your costs are known in advance. No hidden charges No where to spend your money, except

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Announcing the 15th Pilot Cutter Review 2021 from Classic Sailing

22/03 Festivals

Pilot Cutter Review 2022 (Number 16)

The Pilot Cutter Review Schedule 2022 Wednesday 1st June 2022 Charlestown Harbour,  food to buy, free entertainment. Anchor off.  Thursday 2nd June Passage Race to Fowey

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People on Provident

02/03 Educational

Affordable wet weather gear for sailing and boating.

Practical advice 1 First time afloat? 2 Materials 3 Motor Boating 4 Yacht sailing 5 Tall ships and traditional vessels 6 Whats the choice

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faroe islands with classic sailing

12/02 Inspiration

Getting ready for a big adventure.

How to Prepare for a Long Voyage.  Getting the time off – Retirement or sabbatical leave. Before you leave home. How to travel to

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Sailing on Maybe with Classic Sailing

26/01 History

Maybe a history

Maybe a  History 1929 Maybe has a famous history, built in wood with steel frames in 1929 and owned by Jan Jacob Van Rietschoten,

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yoga for tallulah sailors with Sophie

24/01 Inspiration

Sailing & Yoga – Coastal Retreats to Boaty Fitness Camps

The sailing holiday ethos on pilot cutter Tallulah is very much a celebration of healthy coastal living. Sailing ships with blocks and tackles are

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21/01 Inspiration

Grayhound Refit and maintenance winter 2022

The Captain writes Grayhound Ongoing Work Grayhound is continuously being serviced and maintained. Despite being a brand new wooden ship there are still plenty

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Current Voyages

Anny of Charlestown

Cornish Day Sail Adventur on Anny AY150923

Embark

Fri 15-09-2023

Charlestown, Cornwall

Disembark

Fri 15-09-2023

Charlestown, Cornwall

From

£115.00

Anny of Charlestown

Cornish Day Sail Adventur on Anny AY100923

Embark

Sun 10-09-2023

Charlestown, Cornwall

Disembark

Sun 10-09-2023

Charlestown, Cornwall

From

£115.00

Anny of Charlestown

Cornish Day Sail Adventur on Anny AY090923

Embark

Sat 09-09-2023

Charlestown, Cornwall

Disembark

Sat 09-09-2023

Charlestown, Cornwall

From

£115.00