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01/05 Special Voyages

Why I Paint & Sketch On Holiday

Why I Paint & Sketch On Holiday Blog by skipper Debbie Purser You may have noticed that Classic Sailing has voyages with an artist on board

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Pilot Cutter anchored off Shipman Head, Bryher

30/04 Special Voyages

Sailing Holidays in Scilly What to do ashore on Bryher & Sampson

Your Bryher accommodation could be a classic boat Would’t it be cool to stay on an eye catching sailing ship in the Scillies? Your

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West Country Ports - Fowey is a favourite

02/04 Short Breaks and Tasters

Skippers Choice – Favourite West Country Ports

Debbie’s Favourite West Country Harbours As a Classic Sailing skipper for 22 years, I have my favourite ports. They never fail to please me,

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Sailing Holidays with Classic Sailing

12/04 Special Voyages

The Caledonian Canal by Sailing Ship

Voyages from Fort William to Inverness Via Caledonian Canal – Reverse for Inverness to Oban Slicing through the Great Glen of the Scottish Highlands,

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Landing party from Grayhound

27/01 Climate Change

First Cargo deliveries under Sail to the Isles of Scilly

  ISLAND BREWERY SHIPS BEER BY ‘ARMED’ SAILBOAT In an effort to provide local beer and reduce emissions, a brewery based on the Isles

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Eve off the Hangman in New Grimsby Sound, Scillies top ten anchorages

27/01 Special Voyages

Top Ten Anchorages in the Scillies

Top ten anchorages in the Scillies If you’re lucky and have signed up for an Isles of Scilly sailing holiday with us, you might

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Exploring ashore in Cornwall

29/12 No Experience required

Cornwall – South West Coast Path & Exploring Ashore

Sail and Walk the SW Coast Path The South West Coast Path allows you to walk the Cornwall, Devon and Dorset coastal landscape in all its

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Current Voyages

Bounty’s End

Days on the Water and a Night by the Campfire BT060626

Embark

Sat 06-06-2026

Plymouth, UK

Disembark

Sun 07-06-2026

Plymouth, UK

From

£245

Bounty’s End

Sail, Swim, Fish & Wild Camp in Plymouth Sound BT080826

Embark

Sat 08-08-2026

Plymouth, UK

Disembark

Sun 09-08-2026

Plymouth, UK

From

£245

Bounty’s End

Get Back to Nature on the Bank Holiday BT290826

Embark

Sat 29-08-2026

Plymouth, UK

Disembark

Mon 31-08-2026

Plymouth, UK

From

£375

Recently Viewed Voyages

Santa Maria Manuela

Christmas on a 4-Masted Schooner SM231225 V48

Embark

Tue 23-12-2025

Funchal, Madeira

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Sun 28-12-2025

Funchal, Madeira

Limited Spaces Available

From

€1150

Oosterschelde

Winter Sunshine in the Cape Verde 2026 OS050226

Embark

Thu 05-02-2026

Palmeira, Sal, Cape Verde

Disembark

Mon 16-02-2026

Palmeira, Sal, Cape Verde

Limited Spaces Available oosterschelde under sail

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€1925.00

Provident

Exploring Morvern & Mull PV190926

Embark

Sat 19-09-2026

Craobh Haven, Scotland

Disembark

Thu 24-09-2026

Craobh Haven, Scotland

From

£1210