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Sailing Holidays Cornwall

Classic Sailing offers hands on sailing adventures on traditional boats and tall ships all over the world, but our heart is in Cornwall.  Our office is in Portscatho and our home port is the sailors paradise of St Mawes.

Pilot cutter ‘Eve of St Mawes’ was our first charter boat and for 20 years she explored every cove and creek in Cornwall and the Scillies. She has been replaced by her bigger sister ‘Tallulah’ who carries on the company ethos of adventure afloat and exploring ashore by rowing boat. In addition to our St Mawes based pilot cutter we now have a growing fleet of beautiful boats that are based in Cornwall for you to enjoy. Cornwall has many picturesque anchorages, fishing villages and tree lined creeks to visit and plenty of sea room in deep waters without strong tides.

Cornwall & Scilly Voyages

sailing in Cornwall.

Why is Cornwall Great for Sailing?  

North Cornwall offers you the crashing waves, old mine chimneys and rugged scenery straight out of the Poldark TV series. Ideal for surfers but an unfriendly shore for sailing ships. In contrast South Cornwall is just about perfect for sailors.  The Isles of Scilly are a granite archipelago off Lands End are a more advanced sailing playground to navigate but a holiday destination that is out of this world.

The granite cliffs of West Penwith protect Mounts Bay from the North West and the Lizard Peninsula cuts down some of the ocean swell and creates a varied sailing ground to explore around Falmouth Bay. Small fishing villages nestle in every sheltered bay or river from Cadgwith to Cawsand and there are plenty of anchorages where you can be the only boat.

Cornwall is windy, one of the sunniest regions of Britain, un polluted, the seas are unbelievably blue. There are plenty of headlands to aim for, creeks to navigate, picturesque ports small stone quaysides to discover.  

There is a long tradition of boat building, seafaring, fishing and world exploration from Cornish shores. World renowned chefs have made their home here and we can row to some great waterside pubs without a streetlight in sight. 

Isles of Scilly – Wildlife and Sub Tropical Flora

Located 35 miles from Lands End are the Isles of Scilly. Part of Cornwall but totally unique, this archipelago of granite reefs, white sand beaches offers a challenging but rewarding sailing ground. The islands of Tresco, St Agnes, Bryher, St Marys and St Martin all have their charm and there are awesome anchorages off uninhabited islands too. The seas are crystal clear as there are no rivers in the Scillies so it is great for snorkelling. The wide range of habitats from moorland, woodland, dunes, inaccessible rocks and mud and sand flats make a great home for wildlife and staging post for migrating birds.

We have been taking guest crew to this amazing archipelago 35 miles off Lands End  since 1997. If you want to connect with the islands history then sail on a pilot cutter like Tallulah. For 100 years the pilot trade was the islands main economy, before flowers and then tourism took over. Built in oak and larch 44ft Tallulah is an authentic replica of the Scillionian pilot cutters that were based in the islands around 1870-1890’s, so the islanders love to see her visit. Bristol channel Pilot cutter Mascotte also visits The Isles of Scilly regularly.

Also setting sail to the Scillies on a regular basis are larger wooden sailing ships like ‘Grayhound’, ‘Pilgrim’, Anny and Johanna Lucretia. They might not be able to tuck into the smaller anchorages but they can drop their hook in deeper places. All know the isles well and offer a great social atmosphere on board. The islands sit in the Gulf Stream so ashore sub tropical plants flourish and the seas are rich in wildlife with good opportunities to spot dolphins, basking sharks and seals.

The Isles of Scilly have their own destination pages describing what to do on each island, the routes you might sail amongst the islands and some of our favourite anchorages. 

Destination Isles of Scilly
the isles of scilly

A Mecca for Wooden Boats, gaffers, luggers and tall ships

Cornwall has a lot of wooden boats and boatyards. Down here in the SW of England we race Falmouth Oyster Boats and in winter similar half decked gaffers dredge for oysters under sail. In Fowey the iconic Troy keel boats race amongst the moorings and there are numerous boats with bowsprits in all the South Coast ports.

Artists and photographers love us because we help bring historic ships and authentic wooden replicas to Cornish shores. By sailing our vessels you can play a part in creating a maritime spectacle that enhances the small ports and quaysides of Cornwall and brings a timeless quality to a remote anchorage or creek.

Based in St Mawes, Tallulah is a replica of 19th Century pilot cutters that were once a vital part of the economy of Falmouth and the Isles of Scilly.
Three-masted lugger ‘Grayhound’ is a replica of a 1776 Cornish revenue lugger that began chasing smugglers and then became a privateer.
Pilgrim, is an original deep-sea trawler that would have ranged the whole West Country Coast.

Anny and Johanna Lucretia are wooden tall ships under 100ft that were similar to the working trading ships that unloaded cargoes in tiny harbours all round the coast of Europe.

Cornish luggers

Cornwall Sailing Holidays Sailing Voyages


Coastal and River Adventure - PM250623


Sun 25-06-2023

Falmouth, Cornwall


Tue 27-06-2023

Falmouth, Cornwall

Sailing on Pilgrim with Classic Sailing




Roselands Peninsula Sailing Holiday - PM 200623


Tue 20-06-2023

Falmouth, Cornwall


Fri 23-06-2023

Falmouth, Cornwall




Provident Southwest Amble 2024 PV290524


Wed 29-05-2024

Brixham, UK


Mon 03-06-2024

Penzance, Cornwall

Sailing Holidays on Provident with Classic Sailing