Good for

  • Cruising
  • Exploration
  • Ocean passages
  • Training
  • Wildlife
  • Winter sun
  • Sun
  • Racing

Duration

  • 2 - 6 days
  • 1 week +
  • 2 weeks +

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.

View sailing schedule

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.

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.




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 island 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 pilot cutter Pellew loves to explore during the summer months. Anchoring away from the hustle and bustle of island life and experiencing the wild side of Scillies.

Isles of Scilly Sailing

Discover this breathtaking archipelago situated off the coast of Cornwall on board a Cornish Pilot Cutter.
  • Vessel: Agnes
  • Where: Cornwall
  • Duration: 7 days
  • Date: 14 May 2022

Cornwall & Scilly Sailing Jubilee Adventure

Sail and explore the Isles of Scilly on classic tall ship Maybe during the Jubilee celebrations.
  • Vessel: Maybe
  • Where: Cornwall
  • Duration: 8 days
  • Date: 29 May 2022

Isles of Scilly Sailing

Discover this breathtaking archipelago situated off the coast of Cornwall on board a Cornish Pilot Cutter.
  • Vessel: Agnes
  • Where: Cornwall
  • Duration: 7 days
  • Date: 1 June 2022

Isles of Scilly Sailing

Join luxury yacht Skyelark in Plymouth as she explores the Cornish coast and discovers the sub-tropical archipelago of the Isles of Scilly.
  • Vessel: Skyelark
  • Where: Devon
  • Duration: 8 days
  • Date: 4 June 2022

Explore Cornwall & The Isles of Scilly

Sail and explore the Isles of Scilly on classic tall ship Maybe
  • Vessel: Maybe
  • Where: Cornwall
  • Duration: 8 days
  • Date: 7 June 2022

Isles of Scilly Sailing

Discover this breathtaking archipelago situated off the coast of Cornwall on board a Cornish Pilot Cutter.
  • Vessel: Agnes
  • Where: Cornwall
  • Duration: 7 days
  • Date: 8 June 2022

Isles of Scilly Sailing

Join luxury yacht Skyelark in Plymouth as she explores the Cornish coast and discovers the sub-tropical archipelago of the Isles of Scilly.
  • Vessel: Skyelark
  • Where: Devon
  • Duration: 8 days
  • Date: 15 June 2022

Falmouth Classics & Sea Shanty Festival

Discover this breathtaking archipelago situated off the coast of Cornwall on board a Cornish Pilot Cutter.
  • Vessel: Agnes
  • Where: Cornwall
  • Duration: 5 days
  • Date: 16 June 2022

Sailing Adventure to the Isles of Scilly

Explore the beautiful archipelago of the Isles of Scilly on classic boat Pilgrim of Brixham.
  • Vessel: Pilgrim of Brixham
  • Where: Cornwall
  • Duration: 8 days
  • Date: 21 June 2022

Five Island Sailing in the Isles of Scilly

Meet Pettifox in the Isles of Scilly and spend a week exploring all that it has to offer.
  • Vessel: Pettifox
  • Where: Isles of Scilly
  • Duration: 7 days
  • Date: 25 June 2022

Tall Ship Sailing in the Isles of Scilly

Sail and explore the beautiful archipelago of the Isles of Scilly on classic tall ship Maybe.
  • Vessel: Maybe
  • Where: Cornwall
  • Duration: 8 days
  • Date: 25 June 2022

Sailing Adventure to the Isles of Scilly

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

Five Island Sailing in the Isles of Scilly

Meet Pettifox in the Isles of Scilly and spend a week exploring all that it has to offer.
  • Vessel: Pettifox
  • Where: Isles of Scilly
  • Duration: 7 days
  • Date: 2 July 2022

Tall Ship Sailing in the Isles of Scilly

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

Short Break Sailing in the Isles of Scilly

Meet Pettifox in the Isles of Scilly for an exclusive short break exploring the beauty of the islands under sail.
  • Vessel: Pettifox
  • Where: Isles of Scilly
  • Duration: 4 days
  • Date: 9 July 2022

Sailing Adventure to the Isles of Scilly

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

Tall Ship Sailing in the Isles of Scilly

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

Five Island Sailing in the Isles of Scilly

Meet Pettifox in the Isles of Scilly and spend a week exploring all that it has to offer.
  • Vessel: Pettifox
  • Where: Isles of Scilly
  • Duration: 7 days
  • Date: 16 July 2022

Five Island Sailing in the Isles of Scilly

Meet Pettifox in the Isles of Scilly and spend a week exploring all that it has to offer.
  • Vessel: Pettifox
  • Where: Isles of Scilly
  • Duration: 7 days
  • Date: 23 July 2022

Tall Ship Sailing in the Isles of Scilly

Sail and explore the beautiful archipelago of the Isles of Scilly on classic tall ship Maybe.
  • Vessel: Maybe
  • Where: Cornwall
  • Duration: 8 days
  • Date: 23 July 2022

Isles of Scilly Sailing

Discover this breathtaking archipelago situated off the coast of Cornwall on board a Cornish Pilot Cutter.
  • Vessel: Agnes
  • Where: Cornwall
  • Duration: 7 days
  • Date: 29 July 2022

Five Island Sailing in the Isles of Scilly

Meet Pettifox in the Isles of Scilly and spend a week exploring all that it has to offer.
  • Vessel: Pettifox
  • Where: Isles of Scilly
  • Duration: 7 days
  • Date: 30 July 2022

Tall Ship sailing in the Isles of Scilly

Sail and explore the beautiful archipelago of the Isles of Scilly on classic tall ship Maybe.
  • Vessel: Maybe
  • Where: Cornwall
  • Duration: 7 days
  • Date: 1 August 2022

Sailing & Exploring the Isles of Scilly

Discover the breath-taking archipelago of the Isles of Scilly situated off the coast of Cornwall on board a Cornish Pilot Cutter.
  • Vessel: Pellew
  • Where: Cornwall
  • Duration: 7 days
  • Date: 3 August 2022

Isles of Scilly Sailing

Discover this breathtaking archipelago situated off the coast of Cornwall on board a Cornish Pilot Cutter.
  • Vessel: Agnes
  • Where: Cornwall
  • Duration: 7 days
  • Date: 5 August 2022

Five Island Sailing in the Isles of Scilly

Meet Pettifox in the Isles of Scilly for an exclusive short break exploring the beauty of the islands under sail.
  • Vessel: Pettifox
  • Where: Isles of Scilly
  • Duration: 4 days
  • Date: 9 August 2022

Sailing & Exploring the Isles of Scilly

Discover the breath-taking archipelago of the Isles of Scilly situated off the coast of Cornwall on board a Cornish Pilot Cutter.
  • Vessel: Pellew
  • Where: Cornwall
  • Duration: 7 days
  • Date: 10 August 2022

Isles of Scilly Sailing

Discover this breathtaking archipelago situated off the coast of Cornwall on board a Cornish Pilot Cutter.
  • Vessel: Agnes
  • Where: Cornwall
  • Duration: 7 days
  • Date: 12 August 2022

Five Island Sailing in the Isles of Scilly

Meet Pettifox in the Isles of Scilly and spend a week exploring all that it has to offer.
  • Vessel: Pettifox
  • Where: Isles of Scilly
  • Duration: 7 days
  • Date: 13 August 2022

Five Island Sailing in the Isles of Scilly

Meet Pettifox in the Isles of Scilly and spend a week exploring all that it has to offer.
  • Vessel: Pettifox
  • Where: Isles of Scilly
  • Duration: 7 days
  • Date: 20 August 2022

Isles of Scilly Sailing

Join luxury yacht Skyelark in Plymouth as she explores the Cornish coast and discovers the sub-tropical archipelago of the Isles of Scilly.
  • Vessel: Skyelark
  • Where: Devon
  • Duration: 8 days
  • Date: 22 August 2022

Isles of Scilly Sailing

Discover this breathtaking archipelago situated off the coast of Cornwall on board a Cornish Pilot Cutter.
  • Vessel: Agnes
  • Where: Cornwall
  • Duration: 7 days
  • Date: 26 August 2022

Five Island Sailing in the Isles of Scilly

Meet Pettifox in the Isles of Scilly for an exclusive short break exploring the beauty of the islands under sail.
  • Vessel: Pettifox
  • Where: Isles of Scilly
  • Duration: 4 days
  • Date: 27 August 2022

Sailing & Exploring the Isles of Scilly

Discover the breath-taking archipelago of the Isles of Scilly situated off the coast of Cornwall on board a Cornish Pilot Cutter.
  • Vessel: Pellew
  • Where: Cornwall
  • Duration: 7 days
  • Date: 31 August 2022

Tall Ship Sailing in the Isles of Scilly

Sail and explore the Isles of Scilly on classic tall ship Maybe
  • Vessel: Maybe
  • Where: Cornwall
  • Duration: 8 days
  • Date: 1 September 2022

Isles of Scilly Sailing

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