More

Voyage Filters

Adventures, News and Educational Articles

Special Voyages

Share This

Dawn at Sea

31/03 Ocean Passages

Seeing Dawn Break at Sea

Dawn at SeaDawn on a sailing ship out of sight of land is a very special experience.On land you may glimpse the dawn through

Read More
sails art at sea

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

Read More
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

Read More
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,

Read More
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,

Read More
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

Read More
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

Read More
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

Read More

Current Voyages

Grayhound

Round trip: Brittany to the Isles of Scilly GR030926

Embark

Thu 03-09-2026

Douarnenez, Brittany

Disembark

Thu 10-09-2026

Douarnenez, Brittany

From

€1760

Grayhound

Round trip: Brittany to the Isles of Scilly GR230626

Embark

Tue 23-06-2026

Douarnenez, Brittany

Disembark

Tue 30-06-2026

Douarnenez, Brittany

Grayhound crew coming ashore for an evening BBQ on St Martins

From

€1760

Grayhound

2 Night Breton Explorer GR170626

Embark

Wed 17-06-2026

Douarnenez, Brittany

Disembark

Fri 19-06-2026

Douarnenez, Brittany

From

€540