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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. Eve was sold into private use in 2017 and now we 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.

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 Agnes. For 100 years the pilot trade was the islands main economy, before flowers and then tourism took over. Built in oak and larch 46ft Agnes is an authentic replica of a Scillionian pilot cutter that was based in the islands around 1870-1890’s, so the islanders love to see her visit.

Also setting sail to the Scillies on a regular basis are larger wooden sailing ships like ‘Grayhound’, ‘Pilgrim’,  ‘Irene’, ‘Leader’ or ‘Provident’. 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. 

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.

Pegasus is a replicas of 19th Century pilot cutters that were once a vital part of the economy of Falmouth and the Isles of Scilly.
1907 ‘Irene’ is one of the last remaining West Country Trading Ketches that once carried cargoes all around Europe.
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.

Cornish luggers

Cornwall Sailing Holidays Sailing Voyages

Anny of Charlestown

Falmouth Tall Ships 2023 AY140823


Mon 14-08-2023

Charlestown, Cornwall


Sat 19-08-2023

Charlestown, Cornwall

Tall Ships Race Start - photo Tall Ships by Max Mudie at




St Mawes Pilot Cutter Review 2023 MT240523


Wed 24-05-2023

Falmouth, Cornwall


Mon 29-05-2023

Falmouth, Cornwall

sailing holidays on mascotte with classic sailing




Sail on Pilgrim Delivery Mile Building Voyage Falmouth to Brixham PM170723


Mon 17-07-2023

Falmouth, Cornwall


Wed 19-07-2023

Brixham, UK

Sailing holidays on Pilgrim with Classic Sailing