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Isles of Scilly Adventure

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Embark Disembark Vessel DurationVoyage No
Fri 12-09-2025, 14:00Douarnenez, Brittany Fri 19-09-2025, 16:00Douarnenez, Brittany Grayhound 7 NightsGR120925

The Isles of Scilly sits at the crossroads of many traditional sailing routes, with a rich maritime history shaped by their strategic position in the Atlantic out beyond Land’s End. Once a haven for privateers and smuggling luggers like Grayhound in the 18th century, these granite islands remain steeped in stories and natural intrigue. 

The Scillonian’s are proud of their nautical history and independence from the mainland.  The climate is strongly influenced by the Atlantic Ocean and the warming Gulf Stream. Here, the boundary between land and sea is redrawn with each tide, as deep blue channels thread between reefs and islands, only to reveal glittering white beaches as the water falls away. 

Please note that the main language on board ship is French, although the majority of the crew also speak excellent English.

  • Voyage
  • Vessel

Ideal voyage for:

Keen sailors who want a cross channel passage making there and back, romantics that like remote anchorages. Photographers, artists and wildlife enthusiasts will love this time of year with seabirds on migratory routes and seals and dolphins enjoying the empty anchorages.

Highlights:

  • 7 night voyage over 8 days
  • Aiming to make passage to Isles of Scilly and back to DZ
  • Cross the English Channel in the Western Approaches
  • Island hopping with white sand beaches & turquoise seas
  • See the locals race the Gig Boats of an evening.

Grayhound

Vessel type / Rig Three Masted Lugger
Guest Berths 8-10
Beam 19ft
Draft 10.75ft
Deck Length 64ft
Overall Length 108ft
Tonnage 56 tons
Year Built 2012
More about the Vessel

Voyage Description

 

An Introduction to Grayhound

On Grayhound they are now mainly sailing in French waters, therefore the main language onboard is French. Most of the professional crew onboard is able to speak both English and French.

GRAYHOUND is one of the largest sailing luggers in the world today. She was built in Cornwall in 2012 and has a 20m long hull, is 33m overall and a canvas area of 470 square meters. The original plans were those of a three masted lugger from 1776. Luggers from that time were built for speed and swiftness ideal for privateering, smuggling…or for hunting the latter! “Pirate hand-break turns” and cannon firing is always on the menu on Grayhound!

As voyage crew you do not have to have any prior sailing experience or knowledge to join on Grayhound. A positive attitude and a wish for adventure is all! Our experienced crew will make sure that you comfortably and eagerly hoist the sails, make fast the ropes, participate in the manoeuvres, steer the ship and ready the anchor. It is all hands-on and you will be a crucial part of getting to our desired destination. You will learn fast while enjoying the feeling of freedom the ship offers as you get humbled by the sea. 

FULL VOYAGE DESCRIPTION

Sail across the English Channel to the the Isles of Scilly

The Isles of Scilly has 55 islands, but just 5 are inhabited, each with its own character—from the busy hub of St Mary’s to the pastoral farmland on Tresco.

The Isles of Scilly offer an ideal sailing ground for all ages and abilities. 

You’ll explore them hands-on as part of the crew aboard *Grayhound*, one of the largest sailing luggers in the world today. 

Built in 2012 to original 18th-century plans, she’s a fast, powerful ship designed for privateering and smuggling. You don’t need prior sailing experience—just a sense of adventure and a willingness to join in. The professional crew will guide you through sail handling, steering, anchoring, and more. 

Weather dictates our route, with the skipper adapting the plan daily as we cross the English Channel, (Le Manche) and weave between the islands, dropping anchor by white sand beaches or rocky coves. You may see dolphins, seals, puffins, or even sharks. Ashore, the sub-tropical climate supports rare flora and fauna, and the Scillies’ rich history and archaeology offer plenty to explore. 

Swimming, rowing, barbecuing on the beach, or simply soaking in the island way of life are all part of the experience. 

The Isles of Scilly are no ordinary destination, and this is no ordinary way to arrive.

Grayhound in the Caribbean

WINDS, WAVES & WEATHER

Sailors are always at the mercy of the weather – this is especially true on a sail cargo journey, where the priority is to sail for every inch of the way if we can! The Skipper will make the call on the best route and timing for the crossing within the voyage period to make the most of what nature provides, and will keep you updated on the latest forecasts and plans while you’re on board. The channel can sometimes get a bit choppy, as wind and waves are funnelled in from the Atlantic, so take precautions if you are prone to seasickness.

A NOTE ON VOYAGE DESCRIPTIONS

On a sailing voyage we never use the word itinerary, as skippers will always be aiming for the best and safest sailing routes for the forecast. They are as keen as you to include some of the highlights described above, but when it comes to sailing, you have to go with Mother Nature, not fight her. The description provided is based on what we think might be possible, based on past trips, or prior experience, but nothing is guaranteed on a sailing voyage. As such, the scheduled joining ports, routes, activities and/or destinations may be altered. Due to the complexities of weather systems, this may be at very short notice. 

HANDS ON HOLIDAYS

Whether you are an experienced sailor or a complete beginner, the professional crew will train you to be guest crew from the moment you arrive, with the intention that everybody works together to sail the ship. The common thread to all Classic Sailing holidays is ‘Hands on’ participation on ships that use ropes, blocks and tackles and ‘people power’ to set sail. Handling cargo adds an extra dimension – building teamwork and communication skills and leaving you with a great sense of achievement.

SAILING STYLE & LIFE ON BOARD

We cater for a wide range of ages and physical abilities and how much you are expected to do varies a bit between vessels. See the vessel tab above which explains all about the ‘sailing style’ and what to expect in terms of hands on participation. There is a lot of information about day to day life, the ships facilities and accommodation on the vessel pages.

Start & End Port

Douarnenez, Brittany

With its twin harbours, Port Rhu and Port du Rosmeur, Douarnenez is rich in maritime history. A standout attraction is the Port-Musée (maritime museum). The food is also excellent, particularly the local sardines, and there are some great spots for lively evenings listening to traditional Breton tunes.

Kit List

What to pack for a sailing holiday on Grayhound

What is included

  • Duvets, linen, pillows
  • Sailing instruction
  • All meals on board (professional chef)
  • Tea, coffee, biscuits, fruit and day time snacks.
  • Night watch snacks (if applicable)
  • You don't have to do the cleaning, but help with the washing up is always appreciated.
  • Waterproof and insulated jackets and trousers
  • Life Jacket and safety equipment, we also have child automatic life jackets.
  • Charging facilities for phones, cameras and tablets etc.

What is not included

  • Towels
  • Travel to joining port
  • Tours, shore expeditions with any hire vehicle or local guide (optional & shared costs)
  • Personal travel insurance See Topsail Insurance LINK
  • There is no bar on board so you might like to bring a bottle or two of wine to enjoy with meals. You can also buy organic sailed cargo wine, red, white and rose onboard.

What to Bring

Don't forget, Grayhound is 108ft overall so she will not always fit into small yacht marinas and she will often have to anchor off in the bay or port. Be prepared to get into a small boat with your luggage and pack sensibly protecting any vulnerable items like cameras. Grayhound has waterproof and insulated flotation jackets and trousers on board which are very warm. In summer or hot locations you may wish to bring some lightweight waterproofs. Even in the Caribbean you can get tropical downpours or spray on deck when sailing in strong winds. A mobile phone so you can ring the ship in an emergency or if you are running late on joining day. Also it means we can contact you if we have to change the joining port for any reason. Grayhound's phone number will always be supplied with your balance confirmation e-mail. Shoes with a good grip for deck & aloft Rubber Boots or second pair of shoes for wet weather or getting in/out of dinghies Swim suit & beach towel. You are welcome to bring snorkel and mask - especially worth it in the Caribbean or Cape Verde. Suntan lotion & sunglasses - consider sunblock and lip salve protection in Canaries, Cape Verde, Trans Altantic, Caribbean. Sun hat / warm hat, scarves, gloves Clothes that dry quickly. Mix of warm, waterproof & windproof layers Small rucksack for going ashore Travel insurance documents/tickets Personal medicines/ spectacles Spending money/passport Camera/binoculars etc Phone chargers. 240 generator on board UK three pin sockets. We welcome musical instruments and you can plug in ipods or CDs into ships stereo. There are storage areas for each bunk . Please pack in a soft rucksack or bag. A torch is useful as a few baggage spaces are at the foot of bunks with reading light at other end. There is no alcohol to buy on board, so you are welcome to bring a bottle or two to drink with meals. If you decide to buy some on arrival You can also buy Grayhound t shirts, mugs and Breton tops from our ship's shop we accept pounds or euros.

Review

 

Sailing on Grayhound in the Caribbean, March 2024

James recently shared his feedback from his voyage on Grayhound, sailing from St. Lucia to Guadeloupe from 6th to 12th March. He thoroughly enjoyed the experience, rating it as amazing, but he felt the need to share some insights.

The crew comprised 11 people, including a professional skipper, a young mate, a cook, and the boat's Swedish owners, Willie and Oscar. The passengers included two Americans, Connor and Leah, along with James and Nigel Sharp, who was there to write an article about the trip. A young couple joined as volunteer crew but lacked experience, which somewhat impacted the dynamics.

James appreciated the diverse age range and found the mixed sleeping arrangements manageable, though he noted the challenges of sleeping in tropical heat. His prior experience on classic boats like Pilgrim and Johanna Lucretia helped him enjoy working on the boat, though he advises that physical fitness is essential for activities like using the hand winch and rowing in the Caribbean heat.

A significant aspect of the trip was the administrative process of checking into each Caribbean island, which James found somewhat tedious. He also highlighted that Grayhound is a vegetarian boat, which, while not a major issue for him, did limit the culinary experience of the Caribbean.

Despite some minor issues, James emphasises that future passengers should be prepared for a more casual and less professional experience on Grayhound, compared to other vessels. He always felt safe and enjoyed the boat's beauty, describing the atmosphere at times as akin to a 'happy hippy expedition'. The owners' approach to running Grayhound as a business seemed more focused on enjoyment, including evenings with drinks and beach BBQ’s.

Overall, James is grateful for the experience and open to future sailing adventures. He also stayed on in the Caribbean for an extra week, offering to share his discoveries with others. He's curious about Nigel Sharp's upcoming article in Classic Boat, noting Nigel's mixed impressions during the trip.

This is a summary of the comments by James March 2024

Thank you so much to all the Grayhound crew for an unforgettable adventure. I cannot imagine a kinder and better crew with which to sail.

Caroline

Thanks all for a great time, I really enjoyed it. Fastest Channel crossing I have managed!

Barney

An unforgettable experience

Jonathon

We've had two idyllic sailing trips. One particularly fantastic day scrambling over big volcanic rocks down a deep craggy valley to a black sand beach with dramatically high cliffs. Grayhound was waiting, attracting attention because she's so beautiful and unique. Swimming out to her in the clear waters o the Atlantic rates as one of life's highlights.

Grayhound Guest

Fantastic, exhilarating and an honour to be on such a ship.

Des

Excellent company of genuine all round sailors. The wind in my face and the swell beneath. 5 stars for welcome, accommodation on board, safety, quality of sailing, food, skipper and crew.

Barry

Outstanding and unforgettable experience. Loved learning the lug rig, meeting the crew and other guests, playing an active role on board.

Charlie

Brilliant sail on an interesting boat with friendly and knowledgeable people.

Steve
learning to steer at a young age on Grayhound
learning to steer at a young age on Grayhound

Vessel Gallery

Three masted lugger Grayhound is a unique sight and a joy to take photos of. Not only does she look very unusual as it is a rig not seen much now, she has a mission to deliver cargoes under sail, so she is the darling of the press. Photos from Classic Sailing customers, ships crew and professional photographers. We hope it gives a flavour of her sailing, life on board, the people that come, her beautiful sailing grounds and what it is like to live below decks.

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