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Sailing Holidays in the Isles of Scilly

A granite archipelago where the boundary between the land and sea is re-drawn with every tide. The Isles of Scilly are part of Cornwall, but have an island culture and climate shaped by Atlantic Ocean and warm Gulf stream that flows past the islands. The islands and reefs 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.

Most people come on our Classic Sailing holidays as individuals, but a sailing trip to the Isles of Scilly also makes an ideal group trip for both families and adults! If you like the idea of chartering your own Classic Sailing vessel, then do get in touch on our contact us page for dates, prices and availability. 

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Why we love this sailing ground

Explore the Isles of Scilly Under Sail

We have a select collection of traditionally rigged sailing vessels visiting the Isles of Scilly.  They navigate safely between the myriad of rocks and along the channels. You will able to island hop, beachcomb, wildlife watch, snorkel in crystal clear seas and chill out amongst the sea pinks.

At the end of the day you can watch the ocean sunset from wooden decks or enjoy the camaraderie of fellow travellers as you plan the next day’s adventure.

Agnes is a replica of the last pilot cutter to work in the Scillies under sail
Agnes is a replica of the last pilot cutter to work in the Scillies under sail

Interesting Tidal Navigation & Offshore Passage

You could just participate in the steering and sail handling and let the professional crew take you to the Scillies, but there is plenty to learn to if you want more involvement. A voyage to the Scillies has everything a keen sailor or adventurous beginner could want.

No experience is required and most people come on their own - but certain vessels may be more suited to families, beginners or couples. Just get in touch and we can help point you in the right direction - Contact Us.

Keep reading for details on the islands, the vessels that sail there and what to expect on an Isles of Scilly Classic Sailing holiday.

Passage Making to the Isles of Scilly

For the experienced sailor, it provides a terrific opportunity to brush up on your skills in offshore watch-keeping, identifying landfalls and traditional pilotage. If you already have a RYA day skipper then this is a great trip to see tidal curves, transits and clearing bearings in action in a more advanced context.

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 passage from Falmouth to the Scillies is over 60 miles and usually means an early start and a long day. If you start from Newlyn the distance is shorter but you still have 35 miles of offshore sailing with big ships passing Lands End, fast tides, and long ocean swell, so it still feels pretty 'out there.' 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.

Seals 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.

Hoisting topsails on Grayhound
Hoisting topsails on Grayhound

Beach Combing & boats - a way of life

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.

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.

Crew evening BBQ on a deserted island in the Scillies
Crew evening BBQ on a deserted island in the Scillies

Island economy based on the Pilot Trade for 100 years

The pilot trade was a major industry for 100 years on the islands so they extend a warm welcome to pilot cutters like Agnes. Our former charter vessel Eve of St Mawes was another pilot cutter that explored the Isles of Scilly with guest crew every summer for 20 years.

Whilst there are no wooden pilot cutters permanently based in the Isles of Scilly now, 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.


gig racing in the scillies
Inter island rivalry - weekly gig racing in the Scillies

"Wouldn't it be cool to live on a boat mum ?"

For many families the Isles of Scilly are the perfect escape. Islands without cars, white sand beaches, a climate generally better than the mainland, crags to climb and crabs to catch. As you are on the Classic Sailing website we are guessing you are looking for something a littll bit different from a holiday cottage ashore. 

How about a three masted lugger with 8 cannons? You don't need any sailing experience to book a Scillies voyage on Grayhound. Her owners have a young son themselves and they have created the ultimate family holiday: You can live aboard Grayhound with all the cooking provided, island hopping so you can enjoy a different sunset each night, beach BBQ'S, and young professional crew with a creative supply of outdoor activities to keep all ages of kids and teenagers busy

Marshmellows on the camp fire in the Scillies on Grayhound
Marshmellows on the camp fire in the Scillies on Grayhound

Itinerary Dictated by the Weather

We have a good record of getting to the Scillies, but it is not always possible. There are no harbours or anchorages in the Scilly completely safe from all wind directions, so if there is bad weather forecast or heavy swell, the skipper may have to seek more sheltered sailing grounds. The professional crew will always endeavour to give you a holiday as close in spirit to an Isles of Scilly type adventure as they can, even if this means venturing across the English Channel to explore the Channel Islands and Brittany if the weather is more favourable. 

Where do we go in the Scillies? Some of our anchorages are well known. Others, we would rather not tell you about until you are onboard, their secrecy adds to the charm. Read on for our Top Ten Anchorages and details on the different islands. 

Great Bay - St Martins on the Isles of Scilly
Great Bay - St Martins on the Isles of Scilly
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