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Sailing Holidays in the Isles of Scilly


The pace of life is so relaxed, it can take a few days to adjust

Scilly Island Hopping

"A granite archipelago where the boundary between the land and sea is re-drawn with every tide. The Isles of Scilly are separated by deep blue channels slowly reconnect as glittering white beaches emerge with the falling tide. The rippled seabed exposed reveals starfish where we once sailed with hand bearing compass held tight."

Isles of Scilly Holiday Specialists - if you want to live on a boat !

We have been taking guest crew to this amazing archipelago 35 miles off Lands End on our wooden pilot cutter Eve of St Mawes since 1997. Built in oak and larch Eve is an authentic replica of Scillionian pilot cutters that were based in the islands around 1870-1890's, so the islanders love to see her visit. Eve only has a 2m draft so she can get into smaller anchorages than some of our larger vessels.

Set sail to the Scillies

Sailing to the Isles of Scillies next year are pilot cutter Agnes, Eve of St Mawes, and West Country Trading Ketch's 'Irene' and 'Bessie Ellen'. All know the isles well and offer a great social atmosphere on board. Choose from smaller pilot cutters with 5-6 crew, however will involve a longer passage to and from the Scillies, or a larger vessel like Bessie Ellen, Irene or Provident accommodating 8-12 crew, which provide a more stable and bigger vessel to make the passage.

Isles of Scilly Sailing Voyages - vessels,dates and prices

6 page mini-brochure about our Isles of Scilly voyages as a printable PDF

Pilotage & Wildlife

Isles of Scilly with Classic SailingSeals play in the swirling kelp forests, flowers flourish in walled fields and the locals go about their daily business by boat. This is a paradise governed by the wind, waves and tide. Exploring the islands offers an intensive lesson in practical seamanship and navigation for adventurous beginners and experienced sailors alike. The passage from St Mawes or Falmouth, around the Lizard, past the lonely sentinel of Wolf Rock and way out west beyond Lands End, can be challenging or totally benign. The Atlantic Ocean frequently rewards you with sightings of dolphins, pilot whales, sunfish and basking sharks. The islands reveal themselves in tantalising stages as each island becomes distinctive on the horizon.

Once nestled in an anchorage, our landing stage is usually a beach so bare feet and sandals are the order of the day. The pace of life is so relaxed it can take a few days to adjust to this small scale world. At first our crews stride out to circumnavigate an island, but after a few hours you will be happy beach combing, sketching or snoozing amongst the sea pinks. With over a dozen anchorages in the archipelago to choose from and the ever changing Atlantic Ocean all around, no Scillies trip is ever the same.

See our photo gallery from past voyages to the Isles of Scilly

Beach Combing & boats - a way of life

The Scillies boatmen ferry locals, tourists and supplies by boat between the main inhabited islands of St Mary's, Tresco, Bryher, St Martins and St Agnes. Daily lives are dependant on the tides and winds. Shipwreck cargoes over the centuries ocean flotsam has provides a motive for  beach combing. The pilot trade was a major industry for 100 years on the islands so they extend a warm welcome to pilot cutters. Today each island has its own pilot gig boats and the racing each week is very competitive. Often at anchor we salute a hard working gig crew with an evening wine glass -as they power past us with 13ft oars.

Isles of Scilly wildlife expert Will WagstaffWill Wagstaff Scilly Island Expert and Tour Leader with Eve of St Mawes

When in the Isles of Scilly, Eve uses for one day the services of local expert Will Wagstaff. He will take us around one of the off islands and explain, the nature, history, flora and fauna, ornithology and gossip of the Isles. There is no extra charge for his rewarding tour. It makes a brilliant introduction and insight into these fabulous islands in the sun.

Will has an amazing telescope and tripod he carries for all to look through - and an eagle eye for birds and cetaceans. 

Artists on Board and Ashore

The weather and light in the Scillies inspires many artists to visit and some excellent artists live on the Islands so you can visit their studios.  One of Eve's skippers Debbie is a keen artist so she will particularly welcome your efforts on any voyage.

Favourite Anchorages in the Scillies

Where do we go in the Scillies ? Some of our anchorages are well known. Others, like the one in the photo below are SECRET. Actually you can read all about Classic Sailings' favourite anchorages and beaches in the Scillies by following the link below:

Classic Sailings' Top Ten Favorite Island Anchorages in the Scillies



  Sunset in the Scilly Isles


Pick your Sailing Holiday

E.g., 20/12/2014

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"I have very fond memories of my first sailing trip, I'll be going again." Sue, Newbury.
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Customer Comments

"Enjoyed re-capturing a brief view of sailing in the piece of 'living history' that Grayhound repre...

"Best Holiday Ever." What did you enjoy the most ? "Everything" Worst bits - " leaving the boat"...

 " We enjoyed everything about those two days and particularly appreciated your patience and your quiet words when w...

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