Sailing Holidays in the Isles of Scilly

With over five islands to discover, there is no better way to explore this breathtaking cluster of island gems than under sail.

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The Isles of Scilly boasts a plethora of dramatic, rugged coastlines – steep rock faces and deep inlets caused by the continuous pounding of huge rollers coming in from the Atlantic Ocean. These stunning islands feature large stretches of deserted white sandy beaches, dramatic rocky coves, stunning seascapes, amazing archaeological sites, beautiful walks and scenery along miles of coastal and country paths and nature trails. You’ll leave longing to return and questioning how somewhere like this could be part of the UK.




Arriving to the islands by boat is truly magical with an exciting sail across the 28 miles* from Cornwall. Our fleet depart from Plymouth, Penzance and Falmouth and will sail over to the islands in a day, depending on the wind direction. Join wooden pilot cutters Agnes and Pellew, classic ketch Maybe, heritage trawler Pilgrim of Brixham, or for a touch of luxury sail with modern yacht Skyelark to the islands.

If you prefer not to sail over we have one boat called Pettifox that is based on St Mary’s all summer that will meet you off the plane or passenger ferry and sail you around the islands from there. It’s the perfect way to explore the islands with plenty of time each day to go ashore and explore Scilly on foot.

Composed of five inhabited islands – St. Mary’s, St. Martin’s, St. Agnes, Bryher and Tresco (with its world-famous Tresco Abbey Garden )– the entire archipelago is an Area of Outstanding Natural Beauty and it’s easy to see why! There are also numerous uninhabited isles to explore too, each offering a safe haven for wildlife and seabirds.

*As the Isles of Scilly are 28 miles from any other landmass, you will need adventure sailing insurance that covers you for more than 12 miles off shore.

St Martins

Usually the first island you’ll see on the horizon with its red and white Daymark erected in 1683 welcoming you to Scilly,  St Martins is just two miles long yet it has some of the finest beaches in the British Isles, if not the world.

St. Mary’s

The Isles of Scilly’s largest island (population 1,800) and the gateway to the rest of the islands, St Mary’s main settlement is Hugh Town where you’ll find shops, pubs and a post office and plenty of places to sit with an ice cream and take in the view.

Bryher

The smallest of the inhabited islands on The Scillies, Bryher has some beautiful walks and scenery and just 80 people are lucky enough to call it home. Hell Bay Hotel or the Fraggle Rock Pub for a light refreshment is a must for all guests.

Tresco

The second-largest of the islands, Tresco is a subtropical gem and home to the famous Abbey Garden, established in the 1830s by Augustus Smith. This horticultural paradise hosts a spectacular collection of more than 20,000 exotic plants from all corners of the world – many of which cannot be grown anywhere else in Britain.

St Agnes

The southernmost and smallest populated island of the Isles of Scilly is totally unspoilt and astonishingly peaceful. An island of extreme contrasts, with rocky outcrops on its exposed western side to serene beaches with the tranquillity of the sandbar between St. Agnes and Gugh on the other side.

Along with these main islands, there are also a plethora of smaller uninhabited islands that our boats love to explore during the summer months. Anchoring away from the hustle and bustle of island life and experiencing the wild side of Scillies.

Take a look at our Isles of Scilly sailing experiences below

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

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

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

Short Break Sailing in the Isles of Scilly

Meet Pettifox in the Isles of Scilly for a short break private charter experience exploring the beauty of the islands under sail.
  • Date: 16 July 2022
  • Vessel: Pettifox
  • Duration: 4 days
  • Where: St Mary's, Isles of Scilly

Five Island Sailing in the Isles of Scilly

Meet Pettifox in the Isles of Scilly for a whole boat private charter experience exploring the beauty of the islands under sail.
  • Date: 23 July 2022
  • Vessel: Pettifox
  • Duration: 7 days
  • Where: St Mary's, Isles of Scilly

Five Island Sailing in the Isles of Scilly

Meet Pettifox in the Isles of Scilly for a whole boat private charter experience exploring the beauty of the islands under sail.
  • Date: 30 July 2022
  • Vessel: Pettifox
  • Duration: 7 days
  • Where: St Mary's, Isles of Scilly

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

Four Day sailing adventure in the Isles of Scilly

Meet Pettifox in the Isles of Scilly for a short break private charter experience exploring the beauty of the islands under sail.
  • Date: 9 August 2022
  • Vessel: Pettifox
  • Duration: 4 days
  • Where: St Mary's, Isles of Scilly

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

Five Island Sailing in the Isles of Scilly

Meet Pettifox in the Isles of Scilly for a whole boat private charter experience exploring the beauty of the islands under sail.
  • Date: 20 August 2022
  • Vessel: Pettifox
  • Duration: 7 days
  • Where: St Mary's, Isles of Scilly

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

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

Bank Holiday Sailing Weekend on the Isles of Scilly

Meet Pettifox in the Isles of Scilly for a short break private charter experience exploring the beauty of the islands under sail.
  • Date: 27 August 2022
  • Vessel: Pettifox
  • Duration: 4 days
  • Where: St Mary's, Isles of Scilly

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

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

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

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

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 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

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

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
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Destinations

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

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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.

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