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.

View sailing schedule

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

Sailing Adventure to the Isles of Scilly

Explore the beautiful archipelago of the Isles of Scilly on classic boat Pilgrim of Brixham from Falmouth.
  • Date: 30 June 2022
  • Vessel: Pilgrim of Brixham
  • Duration: 8 days
  • Where: Falmouth, Cornwall

Yacht Charter Sailing in Cornwall

Sail with Unity this summer as she offers guests bespoke sailing holidays for whole boat private charter.
  • Date: 30 June 2022
  • Vessel: Unity
  • Duration: 4 days
  • Where: Falmouth, Cornwall

Tall Ship Sailing in the Isles of Scilly

Sail and explore the beautiful archipelago of the Isles of Scilly on classic tall ship Maybe from Penzance.
  • Date: 5 July 2022
  • Vessel: Maybe
  • Duration: 8 days
  • Where: Penzance, Cornwall

Sailing Adventure to the Isles of Scilly

Explore the beautiful archipelago of the Isles of Scilly on classic boat Pilgrim of Brixham from Falmouth.
  • Date: 9 July 2022
  • Vessel: Pilgrim of Brixham
  • Duration: 8 days
  • Where: Falmouth, Cornwall

Sailing to France; Festival Temps Fête Douarnenez

Explore the Breton coast to celebrate the Festival Temps Fête in Douarnenez with a whole boat charter on Unity.
  • Date: 12 July 2022
  • Vessel: Unity
  • Duration: 9 days
  • Where: Falmouth, Cornwall

Yacht Charter Sailing in Cornwall

Sail with Unity this summer as she offers guests bespoke sailing holidays for whole boat private charter.
  • Date: 14 July 2022
  • Vessel: Unity
  • Duration: 4 days
  • Where: Falmouth, Cornwall

Tall Ship Sailing in the Isles of Scilly

Sail and explore the beautiful archipelago of the Isles of Scilly on classic tall ship Maybe from Penzance.
  • Date: 14 July 2022
  • Vessel: Maybe
  • Duration: 8 days
  • Where: Penzance, Cornwall

Private Charter Sailing in Cornwall

Sail with Unity this summer as she offers guests bespoke sailing holidays for whole boat private charter.
  • Date: 23 July 2022
  • Vessel: Unity
  • Duration: 7 days
  • Where: Falmouth, Cornwall

Sailing & Exploring the coast of Brittany

Join Cornish Lugger Grayhound in Penzance as she crosses the Channel to explore the coast of Brittany, France.
  • Date: 30 July 2022
  • Vessel: Grayhound
  • Duration: 10 days
  • Where: Penzance, Cornwall

Tall Ship 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: 1 August 2022
  • Vessel: Maybe
  • Duration: 7 days
  • Where: Cornwall

Classic Sailing to the Isles of Scilly

Discover the breathtaking Isles of Scilly situated off the coast of Cornwall on board a Cornish Pilot Cutter Agnes from Falmouth 
  • Date: 5 August 2022
  • Vessel: Agnes
  • Duration: 7 days
  • Where: Falmouth, Cornwall

Private Charter Sailing in Cornwall

Sail with Unity this summer as she offers guests bespoke sailing holidays for whole boat private charter.
  • Date: 6 August 2022
  • Vessel: Unity
  • Duration: 7 days
  • Where: Falmouth, Cornwall

Falmouth Week Sailing with Irene

Sail with Irene as she explores the Cornish coast during Falmouth Week.
  • Date: 7 August 2022
  • Vessel: Irene
  • Duration: 4 days
  • Where: Falmouth, Cornwall

Isles of Scilly Sailing with Cornish Lugger Grayhound

Sailing adventure on board the Cornish lugger Grayhound discovering the breathtaking archipelago of the Isles of Scilly.
  • Date: 18 August 2022
  • Vessel: Grayhound
  • Duration: 8 days
  • Where: Cornwall

Cornish Coastal Sailing

Spend a week exploring the coast of Cornwall under sail on beautiful classic tall ship Maybe.
  • Date: 19 August 2022
  • Vessel: Maybe
  • Duration: 7 days
  • Where: Falmouth, Cornwall

Private Charter Sailing in Cornwall

Sail with Unity this summer as she offers guests bespoke sailing holidays for whole boat private charter.
  • Date: 20 August 2022
  • Vessel: Unity
  • Duration: 7 days
  • Where: Falmouth, Cornwall

Isles of Scilly Sailing with Tall ship Irene

Discover the sub-tropical archipelago of the Isles of Scilly with classic tall ship Irene.
  • Date: 21 August 2022
  • Vessel: Irene
  • Duration: 7 days
  • Where: Newlyn, Cornwall

Tall Ship Sailing in Cornwall

Join classic tall ship Maybe for adventure sailing and exploration along the beautiful Cornish coast.
  • Date: 26 August 2022
  • Vessel: Maybe
  • Duration: 4 days
  • Where: Falmouth, Cornwall

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: 26 August 2022
  • Vessel: Pellew
  • Duration: 5 days
  • Where: Falmouth, Cornwall

Isles of Scilly Sailing with Pilot Cutter Agnes

Discover the breathtaking Isles of Scilly situated off the coast of Cornwall on board a Cornish Pilot Cutter Agnes from Falmouth 
  • Date: 26 August 2022
  • Vessel: Agnes
  • Duration: 7 days
  • Where: Falmouth, Cornwall

Luxury Yacht Sailing to the Isles of Scilly

Join luxury yacht Skyelark in Plymouth as she explores the Cornish coast and discovers the sub-tropical archipelago of the Isles of Scilly.
  • Date: 27 August 2022
  • Vessel: Skyelark
  • Duration: 8 days
  • Where: Plymouth, Devon

Private Charter Sailing in Cornwall

Sail with Unity this summer as she offers guests bespoke sailing holidays for whole boat private charter.
  • Date: 27 August 2022
  • Vessel: Unity
  • Duration: 4 days
  • Where: Falmouth, Cornwall

Isles of Scilly Sailing with Tall ship Irene

Discover the sub-tropical archipelago of the Isles of Scilly with classic tall ship Irene.
  • Date: 28 August 2022
  • Vessel: Irene
  • Duration: 7 days
  • Where: Newlyn, Cornwall

Private Charter Sailing in Cornwall

Sail with Unity this summer as she offers guests bespoke sailing holidays for whole boat private charter.
  • Date: 1 September 2022
  • Vessel: Unity
  • Duration: 5 days
  • Where: Falmouth, Cornwall

Luxury Yacht Sailing to the Isles of Scilly

Join luxury yacht Skyelark in Plymouth as she explores the Cornish coast and discovers the sub-tropical archipelago of the Isles of Scilly.
  • Date: 2 September 2022
  • Vessel: Skyelark
  • Duration: 8 days
  • Where: Plymouth, Devon

Classic Sailing Taster Weekend in Cornwall

Sail with classic boat Agnes as she explores the diversity of the Cornish coast from Falmouth.
  • Date: 2 September 2022
  • Vessel: Agnes
  • Duration: 3 days
  • Where: Falmouth, Cornwall

Isles of Scilly Sailing with Tall ship Irene

Discover the sub-tropical archipelago of the Isles of Scilly with classic tall ship Irene.
  • Date: 4 September 2022
  • Vessel: Irene
  • Duration: 7 days
  • Where: Newlyn, Cornwall

Private Charter Sailing in Cornwall

Sail with Unity this summer as she offers guests bespoke sailing holidays for whole boat private charter.
  • Date: 7 September 2022
  • Vessel: Unity
  • Duration: 5 days
  • Where: Falmouth, Cornwall

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: 9 September 2022
  • Vessel: Pellew
  • Duration: 4 days
  • Where: Falmouth, Cornwall

Cornish Coastal Sailing

Spend a week exploring the coast of Cornwall under sail on beautiful classic tall ship Maybe.
  • Date: 10 September 2022
  • Vessel: Maybe
  • Duration: 5 days
  • Where: Falmouth, Cornwall

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: 15 September 2022
  • Vessel: Pellew
  • Duration: 6 days
  • Where: Falmouth, Cornwall

Tall Ship Sailing in Cornwall

Join classic tall ship Maybe for adventure sailing and exploration along the beautiful Cornish coast.
  • Date: 16 September 2022
  • Vessel: Maybe
  • Duration: 4 days
  • Where: Falmouth, Cornwall

East Coast Sailing Adventure; Newcastle to Falmouth

Sail with tall ship Blue Clipper for an Ocean mile builder from Newcastle to Falmouth, Cornwall.
  • Date: 19 September 2022
  • Vessel: Blue Clipper
  • Duration: 10 days
  • Where: Newcastle, UK

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: 23 September 2022
  • Vessel: Pellew
  • Duration: 3 days
  • Where: Falmouth, Cornwall

Cornish Coastal Sailing with Tall Ship Irene

Join classic tall ship Irene for sailing and exploration along the beautiful Cornish coast.
  • Date: 25 September 2022
  • Vessel: Irene
  • Duration: 4 days
  • Where: Falmouth, Cornwall

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: 30 September 2022
  • Vessel: Pellew
  • Duration: 4 days
  • Where: Falmouth, Cornwall

Autumn Sailing Weekend in Cornwall

Sail with classic boat Agnes as she explores the diversity of the Cornish coast from Falmouth.
  • Date: 30 September 2022
  • Vessel: Agnes
  • Duration: 4 days
  • Where: Falmouth, Cornwall

Sailing the Coast of Cornwall

Explore Cornwall from the water for an exclusive sailing experience on Eda Frandsen.
  • Date: 30 September 2022
  • Vessel: Eda Frandsen
  • Duration: 4 days
  • Where: Cornwall

Tall Ship Sailing Adventure; Falmouth to Portugal

Sail with tall ship Blue Clipper for an Ocean mile builder from Falmouth, Cornwall - Portimao, Portugal
  • Date: 1 October 2022
  • Vessel: Blue Clipper
  • Duration: 19 days
  • Where: Falmouth, Cornwall

Easter Sailing on Bessie Ellen

Shake off the winter blues with some delightful Spring sailing around Cornwall on tall ship Bessie Ellen.
  • Date: 6 April 2023
  • Vessel: Bessie Ellen
  • Duration: 5 days
  • Where: Fowey, Cornwall

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

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

Weekend Sailing in Cornwall

Shake off the winter blues with some delightful Spring sailing around Cornwall on tall ship Bessie Ellen.
  • Date: 14 April 2023
  • Vessel: Bessie Ellen
  • Duration: 3 days
  • Where: Fowey, Cornwall

Weekend Sailing in Cornwall

Shake off the winter blues with some delightful Spring sailing around Cornwall on tall ship Bessie Ellen.
  • Date: 21 April 2023
  • Vessel: Bessie Ellen
  • Duration: 3 days
  • Where: Fowey, Cornwall

Sailing from Cornwall to Scotland

Join Pellew as she makes the voyage North to the West coast of Scotland. Sail from Cornwall and experience life on the open water.
  • Date: 22 April 2023
  • Vessel: Pellew
  • Duration: 10 days
  • Where: Falmouth, Cornwall

A Sailors’ Voyage to Scotland

Tuck some ocean miles under your belt as you sail with Bessie Ellen from Cornwall to Scotland - the perfect opportunity for a taste of life on the open water.
  • Date: 29 April 2023
  • Vessel: Bessie Ellen
  • Duration: 10 days
  • Where: Fowey, 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

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

Tall Ship 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: 5 August 2023
  • Vessel: Maybe
  • Duration: 7 days
  • Where: Cornwall

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: 10 August 2023
  • Vessel: Pellew
  • Duration: 7 days
  • Where: Falmouth, 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: 12 August 2023
  • Vessel: Bessie Ellen
  • Duration: 10 days
  • Where: Scotland/Cornwall

Tall Ship 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: 12 August 2023
  • Vessel: Maybe
  • Duration: 7 days
  • Where: Cornwall

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: 17 August 2023
  • Vessel: Pellew
  • Duration: 9 days
  • Where: Falmouth, Cornwall

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: 22 August 2023
  • Vessel: Bessie Ellen
  • Duration: 7 days
  • Where: Newlyn, Cornwall

Bank Holiday Sailing in Cornwall

Discover and explore the Cornish Coast with exhilarating sailing by day and hidden anchorages by night onboard Pilot Cutter Pellew.
  • Date: 26 August 2023
  • Vessel: Pellew
  • Duration: 3 days
  • Where: Falmouth, Cornwall

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

Tall Ship 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: 1 September 2023
  • Vessel: Maybe
  • Duration: 8 days
  • Where: Falmouth, Cornwall

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

Tall Ship 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: 9 September 2023
  • Vessel: Maybe
  • Duration: 8 days
  • Where: Falmouth, 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

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

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

Tall Ship Taster Sailing in Cornwall

Enjoy tall ship taster sailing on classic boat Maybe as she explores the coasts of Cornwall.
  • Date: 22 September 2023
  • Vessel: Maybe
  • Duration: 4 days
  • Where: 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
Scotland-Kerrera-castle-sailing

Destinations

Our range of vessels enables us to offer several destinations all over the globe. Which adventure will you choose?

View destinations
Bessie-Ellen-Agnes-Sailing

Our fleet

With vessels of all sizes and each with a unique history and construction, there is no shortage of choice for your sailing holiday.

View fleet