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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

09/05 crew profile

Who are Tallulah’s crew in 22?

Tallulah’s invited mates this year are sailors but between them they are also yurt makers, oyster fishermen, seaweed foragers, historic dockyard managers, yoga teachers,

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sailing in scotland

15/05 Inspiration

Sailing Holidays in Scotland

Mountains High and Seas Rich with Abundant Wildlife Scotland offers you some of the finest sailing waters in the UK and how better to explore

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Sailing Holidays to the Isles of Scilly with Classic Sailing

10/05 Inspiration

Isles of Scilly

Reward yourself with a sailing holiday to the Isles of Scilly Forget flying, forget the large ferries and cruisers. Sailing to the Isles of

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The Tall Ship Guide Book explains adventure sailing holidays on tall ships.

09/05 Educational

All you need to know is in the FREE Tall Ship Guide Book!

104 Pages – 60 photos and diagrams – 23 chapters – 17 Types of tall Ships For people, interested to sail on a tall

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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

Ten Reasons Sailing Holidays are Great Value

Ten Reasons Sailing Holidays are Great Value. 1. You know all your costs in advance. You may run up a bar bill but that

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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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Current Voyages


Charter guests TH240922


Sat 24-09-2022

St Mawes, Cornwall


Fri 30-09-2022

St Mawes, Cornwall

The saloon on pilot cutterTallulah




Tenacious Atlantic Sailing Holiday from Bermuda to Portland UK TNS625


Sat 01-04-2023

St Georges, Bermuda


Sun 30-04-2023

Portland, UK

Sailing holidays on Tall ship Tenacious




Tenacious Caribbean Sailing Holiday from Antigua to Bermuda TNS624


Mon 13-03-2023

Antigua, Caribbean


Mon 27-03-2023

St Georges, Bermuda

Sailing holidays on Tenacious with Classic Sailing