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A Celebration of Sail

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Sun 12-05-2024, 14:00Pasaia, Northern Spain Thu 23-05-2024, 11:00Gloucester Docks, UK Grayhound 11 NightsGR120524

A great voyage for blue water, bay, river and even canal sailing!

Set sail from the idyllic port of Pasaia Itsas Festibala in Northern Spain aboard the Grayhound, a traditional Cornish Lugger dating back to 1776. The voyage across the Bay of Biscay is more than just travel; it’s an immersion into 18th-century seafaring life. Hoist sails, navigate by stars, and drink in the maritime splendour while dolphins play in the wake and seabirds provide escort.

Your destination is no less thrilling: Gloucester’s Tall Ships festival, a bustling waterfront event where the Grayhound will be among the star attractions. Rub shoulders with sailing aficionados, tour other magnificent ships, and recount your own tales of crossing the Bay of Biscay.

  • Voyage
  • Vessel


  • Hands-on sailing experience across the Bay of Biscay
  • Plenty of opportunity to see marine mammals
  • ‘Hands-on’ sailing using traditional ropes, blocks, and tackles
  • Conclude the voyage with a celebration of sail at Gloucester Tall Ship Festival


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!


Setting Sail from Pasaia

You will join Grayhound in Pasaia, a fetching Spanish port where the Bay of Biscay sparkles under the warm, Iberian sun. If you’re able to, we recommend arriving a day early to explore this charming harbour town, nestled along the rugged Basque coastline. The town is steeped in maritime history—something that’s right up any sailor’s alley. Walk past fishermen’s houses and look out for the statue of the French writer, Victor Hugo. Why not head up to the La Plata Lighthouse for a panoramic gaze over the Bay of Biscay – after all, you’ll soon be sailing out there! You can almost hear the old navigators whispering in your ear, urging you to set sail. Navigating up the Bay of Biscay, you’ll traverse waters that present a mix of open ocean and coastal landscapes. The transition from the rocky coasts of Spain to the expansive sea serves as a dynamic backdrop for your journey.

Two sailors hauling lines on the deck of Lugger Grayhound. You can learn the ropes with a sailing adventure through Classic Sailing.

The Natural World

Spring is a great time of year for wildlife enthusiasts. In the Bay of Biscay you’ll find yourself in the heart of one of Europe’s most spectacular seascapes, teeming with marine life. The azure waters and gentle breeze create a mesmerizing, immersive experience. Keep your binoculars handy because you might spot playful dolphins riding the bow wave, and if you’re lucky, majestic whales breaching the surface. It’s also a prime time for birdwatching, with seabirds like gannets and shearwaters soaring overhead.


Grayhound offers a hands-on sailing experience. Under the guidance of skilled professional crew, you’ll get involved in setting the sails, helming, and if you fancy it, even celestial navigation if conditions allow. It’s a taste of 18th-century seamanship brought into the present, and you don’t need prior sailing experience to take part. One of the most rewarding aspects of the trip is the teamwork. Whether you’re a seasoned sailor or a newcomer, there’s a role for everyone on board. Shared responsibilities create a sense of community, and you’ll find that the physical tasks, though demanding, are part of the charm.

Navigating to Bristol & Beyond

Sailing up the Bristol Channel and navigating through the canal system to reach Gloucester is a journey that transitions from the openness of the sea to the more confined, but equally charming, waterways of the British interior. The Bristol Channel is known for its strong tidal ranges, among the highest in the world, which can be both a challenge and an asset. As you navigate northward, you’ll transition from the broad Bristol Channel into the River Severn. After reaching Sharpness, you’ll transition from the river to the canal system. The Gloucester and Sharpness Canal was initially engineered to bypass a particularly hazardous stretch of the River Severn; it’s relatively straight and wide for a canal, specifically designed to accommodate larger vessels like the ones you’re familiar with. This leg of the journey is typically serene, surrounded by lush greenery, pastoral settings, and the occasional old industrial warehouse reminding you of the canal’s working history.

Party Time at Gloucester Tall Ships Festival

Your journey culminates in the Gloucester Tall Ships festival, a gathering of classic ships and maritime enthusiasts. Grayhound will be among the featured vessels, providing an opportunity to compare notes with sailors from other ships. Gloucester Tall Ships Festival is one of the most anticipated maritime events in the UK. It attracts tall ships from around the globe, making the docks come alive with nautical activity. These festivals have been occasions where heritage, tradition, and modern sailing culture coalesce beautifully. As for activities, you can usually expect a robust programme featuring live music, sea shanties, maritime-themed plays, and interactive workshops. There’s often a market selling nautical crafts and foods, as well as a range of shoreside entertainment, from funfair rides to spectacular fireworks in the evening.

Grayhound in Gloucester

Learn as you go

While no prior experience needed for this journey, please be advised that this voyage is partly an open-water crossing, with a night watch system in place and be aware that the Bay of Biscay can at times be challenging – while we don’t want that to put you off, please take some time to consider if this voyage is right for you. Rest assured that Grayhound’s seasoned crew will act as your maritime mentors, schooling you in the art of sailing this iconic vessel so that even the most novice guest will have a safe and fun crossing. Whether it’s hoisting the canvas or plotting a course across open waters, you’ll be invited to take the tiller, read the charts, and keep watch as you navigate through the twilight. It’s a tactile experience that not only connects you with the Lugger but also deepens your relationship with the open sea.


Spring can be a bit unpredictable in terms of weather, so be prepared for a mix of conditions. You might encounter some brisk winds, especially across the Bay of Biscay. While the weather might be a bit on the cooler side, it’s also a refreshing time to sail, and you’ll appreciate the salty breeze in your face.

The sea state can vary, but generally, the Bay of Biscay is known for its lively waters. ‘Grayhound’ is a sturdy vessel, well-equipped for these conditions, and the experienced crew will ensure your safety and comfort throughout the journey.


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.

Start & End Port

Pasaia, Northern Spain


Gloucester Docks, UK

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.



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.


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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