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    Sailing Holidays in Cornwall

    This beautiful county boasts a breath taking coastline with secluded coves and tales of smuggling. With deep azure waters and an ever-present breeze, it's perfect for exploring under sail.

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    Set on the very south-western tip of Britain, Cornwall is an iconic destination, luring visitors from across the globe year on year. Completely surrounded by water, her coastline is intrinsically linked with her rich history, tales of piracy, trade and smuggling intertwining themselves with the breathatkingly beautiful cliffs, hidden coves and sweeping golden sandy bays. She is a land of rugged moorlands and quaint harbours, where tourist towns perch above dramatic cliffs and abandoned engine houses dot the landscape. This beautiful coastline offers plentiful sailing opportunities so take to the water and uncover Cornwall from a whole new perspective!

    VentureSail is based in Cornwall and many of our ships call these waters home, touring the stunning coastline and making trips across to the incredible Isles of Scilly during the summer months. Set sail from Fowey and explore some of Poldark’s filming locations, explore picturesque harbour Charlestown, head to Falmouth to sail across the third deepest natural harbour in the world and hunker down in the secluded Helford for the night, you might even have dolphins for company! Wherever your venture takes you, sailing holidays in Cornwall are a firm favourite for many of our guests and skippers, it is easy to see why.

    Sailing Holidays in Cornwall

    Learning the ropes is a great challenge for sea-dogs and novice sailors alike and sailing in Cornwall provides the perfect opportunity to get to grips with some of the basics or hone existing skills. With a constant breeze and variety of sailing waters at their fingertips, our skippers and crew are able to impart their knowledge, encouraging guests to even take the helm and lead the way.

    The exact itinerary for every sailing holiday is subject to wind and tides however it is likely that we will visit one of the many picturesque Cornish harbours where you can step ashore to sample freshly baked pasties and delicious clotted cream ice cream whilst soaking up the hustle and the bustle of a busy Cornish summer. Away from the crowds, your skipper will endeavour to take you off the beaten track, allowing guests to walk some of the South West Coast Path and discover some hidden gems far from prying eyes, where wildlife abounds.

    Sheltered Cornish coves and Starlit Nights

    Perhaps one of the best parts of staying on a classic ship in Cornwall are the still evenings, where peaceful little coves and rivers become an astronomer’s dream – Cornwall is home to several dark skies sites and the star-gazing here is beautiful. Lying back on the gently rocking deck, away from light pollution, the star-studded sky seems infinite and those patient viewers may observe comets, shooting stars, and the silvery moon. You’ll be swept away by the romance of Cornwall, which has long inspired authors, and its stark contrast to modern life.

    Home Comforts

    In recent years Cornwall has made its mark on the food and drink scene with the county now boasting some of the best produce in the country and after a busy day at sea, food forms an important part of life! With fresh-off-the-boat seafood, fantastic fruit and veg, a range of local meats plus the fabulous variety of Cornish spirits and wines to accompany, there’s plenty to whet the appetite. Explore quirky cafes, popular restaurants and local bakeries whilst ashore before returning to your vessel for a superlative Cornish dining experience made using the finest local produce.

    Read more about sailing in the Isles of Scilly here

    Offshore Sailing Adventure from Portugal to Scotland

    Offshore Sailing Adventure from Portugal to Scotland

    Sail with tall ship Blue Clipper for an Ocean mile builder from the South coast of Portugal to the West coast of Scotland.
    • Date: 31 March 2023
    • Vessel: Blue Clipper
    • Duration: 18 days
    • Where: Portugal/Scotland
    £2,040.00Berths available Details
    Smuggler’s Run Sailing from France

    Smuggler’s Run Sailing from France

    Become part of the crew as you sail Cornish lugger Grayhound on a smugglers cargo run from France to Cornwall!
    • Date: 2 April 2023
    • Vessel: Grayhound
    • Duration: 3 days
    • Where: France/Cornwall
    £450.00Berths available Details
    Easter Sailing on Bessie Ellen

    Easter Sailing on Bessie Ellen

    Discover life aboard a traditional tall ship as you explore the sheltered coastline of Cornwall from Fowey.
    • Date: 6 April 2023
    • Vessel: Bessie Ellen
    • Duration: 5 days
    • Where: Fowey, Cornwall
    £729.00Berths available Details
    Easter Sailing with Lugger Grayhound

    Easter Sailing with Lugger Grayhound

    Discover the coasts of Cornwall, Brittany or the Isles of Scilly as lugger Grayhound makes best use of the wind.
    • Date: 6 April 2023
    • Vessel: Grayhound
    • Duration: 7 days
    • Where: Falmouth, Cornwall
    £1,185.00Berths available Details
    Cornish Coastal Sailing Adventure

    Cornish Coastal Sailing Adventure

    Discover and explore the Cornish Coast with exhilarating sailing by day and hidden anchorages by night onboard Pilot Cutter Pellew.
    • Date: 7 April 2023
    • Vessel: Pellew
    • Duration: 4 days
    • Where: Falmouth, Cornwall
    £595.00Berths available Details
    Taster Sailing Weekend in Cornwall

    Taster Sailing Weekend in Cornwall

    Discover and explore the Cornish Coast with exhilarating sailing by day and hidden anchorages by night onboard Pilot Cutter Pellew.
    • Date: 14 April 2023
    • Vessel: Pellew
    • Duration: 3 days
    • Where: Falmouth, Cornwall
    £460.00Limited berths Details
    Weekend Sailing in Cornwall

    Weekend Sailing in Cornwall

    Discover life aboard a traditional tall ship as you explore the sheltered coastline of Cornwall from Fowey.
    • Date: 14 April 2023
    • Vessel: Bessie Ellen
    • Duration: 3 days
    • Where: Fowey, Cornwall
    £560.00Berths available Details
    Spring Sailing with Lugger Grayhound

    Spring Sailing with Lugger Grayhound

    Discover the coasts of Cornwall, Brittany or the Isles of Scilly as lugger Grayhound makes best use of the wind.
    • Date: 15 April 2023
    • Vessel: Grayhound
    • Duration: 7 days
    • Where: Falmouth, Cornwall
    £1,185.00Berths available Details
    Tall Ship Sailing with Cornwall Wildlife Trust

    Tall Ship Sailing with Cornwall Wildlife Trust

    Explore the Cornish coast with tall ship Bessie Ellen as she partners with Cornwall Wildlife Trust to deliver a wildlife watching extravaganza!
    • Date: 21 April 2023
    • Vessel: Bessie Ellen
    • Duration: 3 days
    • Where: Fowey, Cornwall
    £560.00Berths available Details
    Mile Builder Sailing from Cornwall to Devon

    Mile Builder Sailing from Cornwall to Devon

    Enjoy sheltered coastal sailing from Cornwall to Devon as you learn the ropes of a traditional wooden lugger.
    • Date: 24 April 2023
    • Vessel: Grayhound
    • Duration: 3 days
    • Where: Cornwall/Devon
    £695.00Berths available Details
    Smuggler’s Run Sailing from Cornwall

    Smuggler’s Run Sailing from Cornwall

    Become part of the crew as you sail Cornish lugger Grayhound on a smugglers cargo run from Cornwall to France!
    • Date: 7 May 2023
    • Vessel: Grayhound
    • Duration: 3 days
    • Where: Cornwall/France
    £450.00Berths available Details
    Sailor’s Voyage to Cornwall

    Sailor’s Voyage to Cornwall

    Join Maybe as she makes the voyage South from the West coast of Scotland to Cornwall.
    • Date: 2 June 2023
    • Vessel: Maybe
    • Duration: 5 days
    • Where: Scotland/Cornwall
    £695.00Limited berths Details
    Mile Building Taster from Devon to Cornwall

    Mile Building Taster from Devon to Cornwall

    Join Pilgrim of Brixham as she makes a journey from Brixham to Falmouth to see the south coast of England from a breathtaking viewpoint.
    • Date: 6 June 2023
    • Vessel: Pilgrim of Brixham
    • Duration: 4 days
    • Where: Cornwall/Devon
    £250.00Berths available Details
    Taster Sailing in Cornwall

    Taster Sailing in Cornwall

    Sail with heritage vessel Pilgrim of Brixham to explore the beautiful coastline that Cornwall has to offer.
    • Date: 11 June 2023
    • Vessel: Pilgrim of Brixham
    • Duration: 3 days
    • Where: Falmouth, Cornwall
    £435.00Berths available Details
    Falmouth Classics & Sea Shanty Sailing

    Falmouth Classics & Sea Shanty Sailing

    Join Pilgrim of Brixham as she takes part in the annual Falmouth Classics Regatta and Sea shanty Festival.
    • Date: 15 June 2023
    • Vessel: Pilgrim of Brixham
    • Duration: 4 days
    • Where: Falmouth, Cornwall
    £555.00Berths available Details
    Falmouth Classics & Sea Shanty Festival

    Falmouth Classics & Sea Shanty Festival

    Sail and race with Escape as she takes part in the iconic Falmouth Classics Regatta and Sea Shanty Festival.
    • Date: 16 June 2023
    • Vessel: Escape
    • Duration: 4 days
    • Where: Falmouth, Cornwall
    £550.00Berths available Details
    Classic Sailing in the Isles of Scilly

    Classic Sailing in the Isles of Scilly

    Discover the sub-tropical archipelago of the Isles of Scilly with a tall ship adventure on classic boat Maybe.
    • Date: 17 June 2023
    • Vessel: Maybe
    • Duration: 7 days
    • Where: Penzance, Cornwall
    £1,455.00Berths available Details
    Sailing the Isles of Scilly

    Sailing the Isles of Scilly

    Explore the beautiful archipelago of the Isles of Scilly on classic boat Pilgrim of Brixham from Falmouth.
    • Date: 20 June 2023
    • Vessel: Pilgrim of Brixham
    • Duration: 8 days
    • Where: Falmouth, Cornwall
    £1,325.00Berths available Details
    Classic Sailing in the Isles of Scilly

    Classic Sailing in the Isles of Scilly

    Discover the sub-tropical archipelago of the Isles of Scilly with a tall ship adventure on classic boat Maybe.
    • Date: 25 June 2023
    • Vessel: Maybe
    • Duration: 7 days
    • Where: Penzance, Cornwall
    £1,455.00Berths available Details
    Sailing the Isles of Scilly

    Sailing the Isles of Scilly

    Explore the beautiful archipelago of the Isles of Scilly on classic boat Pilgrim of Brixham from Falmouth.
    • Date: 29 June 2023
    • Vessel: Pilgrim of Brixham
    • Duration: 8 days
    • Where: Falmouth, Cornwall
    £1,325.00Berths available Details
    Classic Sailing in the Isles of Scilly

    Classic Sailing in the Isles of Scilly

    Discover the sub-tropical archipelago of the Isles of Scilly with a tall ship adventure on classic boat Maybe.
    • Date: 3 July 2023
    • Vessel: Maybe
    • Duration: 7 days
    • Where: Penzance, Cornwall
    £1,455.00Limited berths Details
    Sailing the Isles of Scilly

    Sailing the Isles of Scilly

    Explore the beautiful archipelago of the Isles of Scilly on classic boat Pilgrim of Brixham from Falmouth.
    • Date: 8 July 2023
    • Vessel: Pilgrim of Brixham
    • Duration: 8 days
    • Where: Falmouth, Cornwall
    £1,325.00Berths available Details
    Mile Building Taster from Cornwall to Devon

    Mile Building Taster from Cornwall to Devon

    Join Pilgrim of Brixham as she makes a journey from Falmouth to Brixham and see the south coast of England from a breathtaking viewpoint.
    • Date: 17 July 2023
    • Vessel: Pilgrim of Brixham
    • Duration: 3 days
    • Where: Cornwall/Devon
    £250.00Berths available Details
    A Sailors’ Voyage to Cornwall

    A Sailors’ Voyage to Cornwall

    Sail with Bessie Ellen as she marks the end of summer with a journey from Scotland to her home of Cornwall.
    • Date: 22 July 2023
    • Vessel: Bessie Ellen
    • Duration: 10 days
    • Where: Scotland/Cornwall
    £1,627.00Berths available Details
    Sailing from Scotland to Cornwall

    Sailing from Scotland to Cornwall

    Join Pellew as she makes the voyage South from the West coast of Scotland to Cornwall.
    • Date: 22 July 2023
    • Vessel: Pellew
    • Duration: 10 days
    • Where: Mallaig, Scotland
    £1,515.00Berths available Details
    Exploring the Isles of Scilly With Pilot Cutter Pellew

    Exploring the Isles of Scilly With Pilot Cutter Pellew

    Discover the breath-taking archipelago of the Isles of Scilly situated off the coast of Cornwall on board a Cornish Pilot Cutter from Falmouth.
    • Date: 3 August 2023
    • Vessel: Pellew
    • Duration: 7 days
    • Where: Falmouth, Cornwall
    £1,295.00Limited berths Details
    Offshore Sailing from Ireland to Cornwall

    Offshore Sailing from Ireland to Cornwall

    Join tall ship Maybe as she makes an open water voyage from Cork, Ireland to Falmouth, Cornwall.
    • Date: 7 August 2023
    • Vessel: Maybe
    • Duration: 7 days
    • Where: Cornwall/Ireland
    £1,190.00Berths available Details
    Sailing & Exploring Brittany

    Sailing & Exploring Brittany

    Set sail with Pellew from Falmouth and make your way across the English Channel to discover coasts of Brittany.
    • Date: 10 August 2023
    • Vessel: Pellew
    • Duration: 10 days
    • Where: Falmouth, Cornwall
    £1,930.00Berths available Details
    Sailing the Isles of Scilly with Bessie Ellen

    Sailing the Isles of Scilly with Bessie Ellen

    Explore the beautiful archipelago of the Isles of Scilly with classic boat Bessie Ellen under sail.
    • Date: 10 August 2023
    • Vessel: Bessie Ellen
    • Duration: 7 days
    • Where: Newlyn, Cornwall
    £1,312.00Limited berths Details
    Sailing to Brittany & the Channel Islands

    Sailing to Brittany & the Channel Islands

    Set sail with Pellew from Falmouth and make your way across the English Channel to discover the Channel Islands and the North Coast of Brittany.
    • Date: 20 August 2023
    • Vessel: Pellew
    • Duration: 10 days
    • Where: Falmouth, Cornwall
    £1,930.00Berths available Details
    Exploring the Isles of Scilly With Pilot Cutter Pellew

    Exploring the Isles of Scilly With Pilot Cutter Pellew

    Discover the breath-taking archipelago of the Isles of Scilly situated off the coast of Cornwall on board a Cornish Pilot Cutter from Falmouth.
    • Date: 30 August 2023
    • Vessel: Pellew
    • Duration: 7 days
    • Where: Falmouth, Cornwall
    £1,295.00Berths available Details
    Cornish Coastal Sailing Adventure

    Cornish Coastal Sailing Adventure

    Discover and explore the Cornish Coast with exhilarating sailing by day and hidden anchorages by night onboard Pilot Cutter Pellew.
    • Date: 7 September 2023
    • Vessel: Pellew
    • Duration: 6 days
    • Where: Falmouth, Cornwall
    £995.00Berths available Details
    Taster Sailing in Cornwall

    Taster Sailing in Cornwall

    Discover and explore the Cornish Coast with exhilarating sailing by day and hidden anchorages by night onboard Pilot Cutter Pellew.
    • Date: 15 September 2023
    • Vessel: Pellew
    • Duration: 4 days
    • Where: Falmouth, Cornwall
    £595.00Berths available Details
    Sailing from Ireland to Cornwall & the Isles of Scilly

    Sailing from Ireland to Cornwall & the Isles of Scilly

    Join Cherokee in Ireland as she prepares to set sails to to Cornwall, via the sub-tropical archipelago of the Isles of Scilly.
    • Date: 16 September 2023
    • Vessel: Cherokee
    • Duration: 9 days
    • Where: Ireland/Cornwall
    £1,465.00Berths available Details
    East Coast Sailing Adventure; Newcastle to Falmouth

    East Coast Sailing Adventure; Newcastle to Falmouth

    Sail with tall ship Blue Clipper for an Ocean mile builder from Newcastle to Falmouth, Cornwall.
    • Date: 18 September 2023
    • Vessel: Blue Clipper
    • Duration: 10 days
    • Where: Newcastle, UK
    £2,190.00Berths available Details
    Taster Sailing in Cornwall

    Taster Sailing in Cornwall

    Discover and explore the Cornish Coast with exhilarating sailing by day and hidden anchorages by night onboard Pilot Cutter Pellew.
    • Date: 21 September 2023
    • Vessel: Pellew
    • Duration: 5 days
    • Where: Falmouth, Cornwall
    £790.00Berths available Details
    Sailing the Coasts of Devon & Cornwall

    Sailing the Coasts of Devon & Cornwall

    Explore the coasts of Devon and Cornwall with adventure yacht Cherokee.
    • Date: 26 September 2023
    • Vessel: Cherokee
    • Duration: 6 days
    • Where: Cornwall/Devon
    £935.00Berths available Details
    Taster Sailing in Cornwall

    Taster Sailing in Cornwall

    Discover and explore the Cornish Coast with exhilarating sailing by day and hidden anchorages by night onboard Pilot Cutter Pellew.
    • Date: 29 September 2023
    • Vessel: Pellew
    • Duration: 4 days
    • Where: Falmouth, Cornwall
    £595.00Berths available Details
    Tall Ship Sailing Adventure; Falmouth to Spain

    Tall Ship Sailing Adventure; Falmouth to Spain

    Sail with tall ship Blue Clipper for an ocean crossing experience from Falmouth, Cornwall to La Coruna, Spain.
    • Date: 30 September 2023
    • Vessel: Blue Clipper
    • Duration: 10 days
    • Where: Cornwall, Spain
    £2,190.00Berths available Details
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    • Fleet
      • See Our Fleet
        • Agnes
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        • Eye of the Wind
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