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Island Hopping in the Scillies

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Embark Disembark Vessel DurationVoyage No
Sun 23-06-2024, 14:00Penzance, Cornwall Wed 03-07-2024, 11:00Falmouth, Cornwall Grayhound 10 NightsGR230624

Sail 64ft sailing lugger Grayhound to the Isles of Scilly and enjoy life on board this moveable holiday base. Fun and action packed while being a peaceful escape to the beautiful quiet islands. What will you discover ? Beach cooking, hikes ashore, pulling on ropes, steering, learning to sail, living together and big meals around the table.

This voyage is for beginners and seasoned sailors alike but be aware that the voyage between Cornwall and the Islands can on occasion be a bit rough. You’ll be there in no time tough and you’ll soon find it is well worth it once you get there! If you feel unsure please contact us and ask for further information. Classic Sailing +44 1326 53 1234

  • Voyage
  • Vessel


  • Exciting Offshore passage to Scilly
  • Different anchorages each night
  • Ocean Sunsets & wildlife
  • A world where tides and boats are a way of life
  • White sand beaches & clear seas


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

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. 

Some of the trips are more demanding than others. Make sure to read the voyage descriptions properly before you book your adventure. If you feel unsure please contact us and ask for further information. Classic Sailing +44 1326 53 1234


You Join Grayhound in Penzance, Cornwall

Nestled on Cornwall’s southwestern tip, Penzance is a charming coastal town laden with rich history and a dash of pirate lore. If you’re able to, why not arrive a day early and explore the town. Meandering through its cobbled streets, and you might find yourself in Morrab Gardens, a subtropical haven filled with unexpected botanical treasures. Seek out the Jubilee Pool, an Art Deco lido by the sea; it’s the perfect spot to dip your toes and get a feel for the ocean’s embrace. As evening approaches, it’s customary to indulge in some fresh Cornish seafood at one of the local eateries. And if you’re inclined, a pint at the Admiral Benbow – an inn straight out of Treasure Island – is a must. You’ll feel the weight of seafaring tales all around, as if the town itself is gently whispering stories of ancient mariners and their adventures. Soon it’ll be time to join the ship and get acquainted with Grayhound, the Crew and your fellow guests.

Along the way

Setting out from Penzance, you’ll feel the cool breeze of Mount’s Bay, with the majestic St. Michael’s Mount looming on your port side. This tidal island, with its medieval castle and chapel, stands as a sentinel of Cornwall’s past. As Grayhound slices through the waters, Land’s End will beckon from the distance – Britain’s rugged southwestern tip, where legends say the land and myths intertwine. First one to spy the Wolf Rock Lighthouse gets a biscuit before you loose sight of land all together (unless its a very clear day) for several hours.

This stretch of sea is a playground for Mother Nature. Keep an eye out for playful dolphins, riding the bow wave. Seabirds, too, make their presence known: from the gannets with their pointed wings to the elusive puffins that might just grace you with a fleeting glance.

You will be fully involved in setting sails, reefing, trimming, jibing and steering as we make our way through the waves of the Celtic Sea. The crew will teach and guide you all the way. Watch the hues of the ocean shift from deep blues to shimmering turquoises. After 10-12 hrs and about 30 miles we will reach the Isles of Scilly and head for anchorage by one of its 55 islands.

Island Explorers

The weather will play a large part in deciding in which of the other islands you visit. The unpredictable whims of the winds and tides will tell us where we go. Sailing between them is hands-on and you will be part of the watch teams helping to navigate from island to island. Keep an eye on the water as Dolphins, Seals, Minke Whales, Basking Sharks and Sunfish call the waters around the Islands home. You may even spot puffins!

You will drop anchor by sandy white beaches, rocky sea cliffs and secluded coves. The crystal clear waters and the (hopefully) mild and sunny weather will invite you for a swim or a row ashore and have a relaxed beach stroll. Or a hike to one of the many historical sites and learn more about the rich and dramatic history and archaeology of the Scillies. As you ease into the more simple and peaceful way of life you may enjoy a beer or two onboard or head for the beach and make a barbecue with fresh locally grown food as the sun sets.

Disembarking in Falmouth

The conclusion of your voyage brings you to Falmouth, a historic harbour town nestled in Cornwall. This charming coastal town warmly welcomes you as Grayhound docks, marking the end of your maritime journey. Falmouth, with its rich maritime heritage, offers a delightful place to explore, with opportunities to learn about Cornwall’s seafaring traditions and enjoy its coastal attractions. If you’re able to, we recommend staying an extra day in Falmouth to explore the town and surrounding area. Visit the National Maritime Museum Cornwall and see the national small boats collection. Grab lunch at Windjammer Café, sit out on the balcony and enjoy watching the hustle and bustle of the harbour below – you’ll likely be able to see Grayhound from there! There are also 2 train stations right in the town, close to the harbour, perfect for your onward journey home or going further afield to see Cornwall’s many visitor attractions such as the Eden ProjectTintagel Castle and the Minack Theatre to name just a few.


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. You are out in the Atlantic here, so the swells can be long and large, and the wind sometimes gusty. However being an archipelago with endless bays, channels and lees in which to shelter, there’s usually some calm water to be found somewhere if the weather picks up!


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. 


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.


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.

Explore the beautiful Isles of Scilly after the school holidays and relax on the Grayhound lugger
The view of Tresco from Bryer

Start & End Port

Penzance, Cornwall

Penzance harbour is the home port of the Car and Passenger Ferry to the Scillies. There is only one ferry called the Scillionian – a very distinctive white vessel that moors up on the seaward Pier to the Penzance Wet Dock. If the ferry is in port you can usually see it accross the harbour from the Penzance Railway Station car park.

The outer harbour is tidal and dries out to mud so the wet dock is the place that Classic Sailing vessels will use to start or end your voyage, so if you head for the Penzance – Scilly Ferry on foot or follow the road signs for the Scillionian Ferry you will find the Wet Dock. Next door is the famous Penzance Swimming Lido with bright blue flags.

The Penzance Wet Dock has a lock gate that can only be entered 1.5 hrs before or after high water, and the entrance is exposed to Southerly or SE gales, so it is possible the skipper of your vessel may have to dock in the nearby fishing port of Newlyn.

Falmouth, Cornwall

We now have several vessels that use Falmouth as a joining or leaving port. As every vessel is different, and we do not have our own pontoon there, all joining instructions are slightly different. Any changes will be communicated to you before your voyage start date.

This is a list of the likely joining locations, but sometimes the ship can also be at anchor. Read the vessel’s joining instructions carefully for full details.

Port Pendennis is the small marina behind the National Maritime Museum Cornwall and the nearest rail station is ‘Falmouth Town’ (3 mins walk). The Maritime Museum has a big tower like a lighthouse so aim for that and at the entrance, turn right and walk down the side of the museum. The gate to the marina is behind the museum building.

Custom House Quay is a stone quay enclosing a small wet dock in the Centre of Falmouth Town. It is used for some of the foot ferries to St Mawes in the peak summer. Only 5 minutes walk from Falmouth Town Station if you head towards the town centre. Situated at the Maritime Museum end of the high street and has its own short stay car park between Trago Mills Store and the Chain Locker Pub if you are driving and want to drop your bags first.

Falmouth Visitors Yacht Haven is about 100 yards beyond Custom House Quay but if walking from the rail station towards town it is best if you walk accross Custom House Quay short term car park and nip through the alley tunnel through the Chain Locker Pub. The yacht haven is a small marina only yards from Falmouth main shopping street (Arwenack St), tucked away down the bottom of Quay Street.

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.



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.


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


An unforgettable experience


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.


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.


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


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

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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