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.
Sub-Tropical Island Explorer: Pilot Cutter Sailing to the Isles of Scilly
- 20 July 2025, 7 days
- Vessel: Pellew
- Port: Falmouth, Cornwall
- Board type: Full Board
Sub-Tropical Island Explorer: Pilot Cutter Sailing to the Isles of Scilly
- 24 May 2025, 7 days
- Vessel: Pellew
- Port: Falmouth, Cornwall
- Board type: Full Board
Sub-Tropical Island Explorer: Pilot Cutter Sailing to the Isles of Scilly
- 15 May 2025, 7 days
- Vessel: Pellew
- Port: Falmouth, Cornwall
- Board type: Full Board
Sub-Tropical Island Explorer: Pilot Cutter Sailing to the Isles of Scilly
- 28 July 2025, 7 days
- Vessel: Pellew
- Port: Falmouth, Cornwall
- Board type: Full Board
Private Yacht Charter Sailing to the Isles of Scilly
- 29 July 2025, 8 days
- Vessel: Emma Claire
- Port: Cornwall
- Board type: Full Board
Sub-Tropical Island Explorer: Pilot Cutter Sailing to the Isles of Scilly
- 24 August 2025, 7 days
- Vessel: Pellew
- Port: Falmouth, Cornwall
- Board type: Full Board
Sub-Tropical Island Explorer: Pilot Cutter Sailing to the Isles of Scilly
- 16 August 2025, 7 days
- Vessel: Pellew
- Port: Falmouth, Cornwall
- Board type: Full Board
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 cutter Pellew, classic ketch Maybe, heritage trawler Pilgrim of Brixham, tall ship Blue Clipper or heritage ketch Bessie Ellen to make the journey.
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.
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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