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    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.

    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.




    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

    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
    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
    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
    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
    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
    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
    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
    Scotland-Kerrera-castle-sailing

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