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Celebrating Christmas & New Year While Crossing the Ocean!

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Fri 20-12-2024, 14:00Las Palmas, Gran Canaria Fri 17-01-2025, 11:00Castara Bay, Tobago Grayhound 28 NightsGR031224

Join Grayhound on a transatlantic sailing adventure from Las Palmas to Casara Bay, Tobago this winter! Experience hands-on sailing, celestial navigation, and the thrill of open-sea voyaging. Spot diverse marine wildlife and enjoy starry nights and trade winds. Conclude your journey in the serene Tobago, exploring its lush landscapes and tranquil beaches.

Celebrating Christmas and New Year at sea is a memorable experience, especially on Sailing Luger in the middle of a TransAtlantic crossing! Mixing traditional festivities with the unique customs of a life lived on the ocean waves, it’s an opportunity to reflect, celebrate, and look forward to the adventures that lie ahead.

This voyage is perfect for those seeking a winter getaway, ideal for adventurers interested in a long-distance sea crossing and island hopping. It’s perfect for anyone looking to escape the winter blues or celebrate the festive season in a unique, oceanic setting. Whether you’re a seasoned sailor or a newcomer eager to learn the ropes, the diverse experiences from navigation to night watches will enrich your journey.

  • Voyage
  • Vessel


  • Transatlantic crossing on a Sailing Luger!
  • Great practice for those working towards sailing qualifications
  • Action packed voyage with plenty to see and do
  • Stand night watches with the professional crew
  • Fantastic varied sailing in great company


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 


Departing from Las Palmas

Before you hoist the sails aboard Grayhound, Las Palmas invites you to bask in its vibrant ambiance. If time permits before your departure, explore the cobbled streets of Vegueta, the historic district, where the echoes of the past blend seamlessly with lively cafés and boutiques. For a touch of nature, the Jardín Botánico Canario offers a tranquil escape with its exotic flora. Both spots provide a delightful contrast to the forthcoming sea journey.

When you’re ready to join the ship, Grayhound’s friendly international crew will welcome you aboard and help you get settled in. As you leave the harbour, the open sea beckons!

Along the Way

This is a Trans-Atlantic adventure – a true ocean crossing and at the top of many sailors bucket lists! As Grayhound slices through the Atlantic, you’ll be treated to a panorama of the sea’s ever-changing moods and the wildlife that calls these waters home. Look out for the playful dolphins racing alongside the ship, and on luckier days, whales may breach the surface in a spectacular display. Bird enthusiasts will revel in spotting rare seabirds like the Petrel or the majestic Albatross, each sighting adding to the rich tapestry of your maritime adventure.

You’ll be at sea for 2-3 weeks solidly. As a member of the voyage crew, you’ll be actively involved in sailing the ship. This means no experience is necessary but a willingness to learn is crucial. You’ll handle ropes, set sails, and perhaps even climb the rigging. The crew will teach you all the necessary skills progressively, ensuring you become more confident with each task.

During the day, when not on watch, there’s time to learn about celestial navigation, read, write in your journal, or simply gaze at the endless sea. Night brings its own magic with star-filled skies and the tranquility of the ocean. Night watches can be serene yet awe-inspiring, as you navigate by the stars and listen to the sound of the sea against the hull. It’s a time for introspection and experiencing the profound quietude that only the ocean can offer.

offshore on Grayhound

Arriving in Tobago

After weeks of vast, open ocean and the rhythmic life at sea, the first sight of Tobago’s lush, green hills emerging on the horizon is exhilarating. The sight of land brings a surge of excitement amongst the crew and passengers alike. It’s a poignant moment, marking the end of a long journey and an extraordinary adventure.

As Grayhound navigates closer, the contours of the coastline become clearer. The deep blues of the open ocean gradually give way to the vibrant turquoise of shallower waters. Castara Bay reveals itself, framed by golden sands and dense tropical forests that descend right to the water’s edge. The beauty of the bay, with its traditional wooden fishing boats bobbing gently in the water, paints a picture of tranquility and untouched nature.

Setting foot on solid ground after weeks of the constant sway of the ship can be a surreal experience. There’s often a moment of readjustment as your legs adapt to the stillness of the earth. The warm sand underfoot and the gentle lapping of waves at the shore provide a stark contrast to the creaking of ropes and the slap of waves against the hull that defined daily life at sea. The local community in Castara is known for its warmth and hospitality. Arriving sailors are often greeted with friendly smiles and an eagerness to share the treasures of their home

castara bay, tobago


Embarking in December, you’ll be graced with the North-East trade winds propelling you smoothly across the Atlantic. Expect mild to moderate seas and favourable sailing conditions, typical for this time of year. Nighttime can bring cooler temperatures, so packing layers will ensure comfort as you stand watch under the starlit sky.


Late October, weather in this region is generally mild, with average temperatures ranging from 15-23°C. Sea conditions are typically calm, but like any maritime adventure, be prepared for varying conditions. Winds are mostly favourable, making it a prime time for sailing enthusiasts to enjoy smooth sailing and occasional brisk breezes.


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.

Start & End Port

Las Palmas, Gran Canaria

All joining locations should be used as a guide only. Detailed joining locations will be sent to you prior to your voyage start date, if in doubt call the ship’s phone using the information in your final confirmation email.

Castara Bay, Tobago

castara bay, tobago


How to Get There

If you’re coming from the UK, Europe, or North America, the most straightforward route is to fly into Trinidad’s Piarco International Airport. From there, it’s a quick hop to Tobago’s ANR Robinson International Airport. Australians might need to make a few more connections, likely via North America or Europe. Alternatively, a ferry from Trinidad to Tobago takes around 2.5 hours. If you’re renting a car, the drive from the Tobago airport to Castara Bay is about 45 minutes.

What to Do in Castara Bay

The historical landmark that stands out is Fort Bennett, providing not just a slice of history but also a great vantage point for sweeping views.

Expect a genuinely local, Tobagonian experience in Castara Bay, a place that’s managed to dodge commercialisation. Keep an eye out for local festivals, particularly anything to do with fishing.

Sites of Interest to a Sailor
As a sailor, you’ll appreciate the natural harbour. It’s a fishing village, so don’t expect a marina with all the bells and whistles, but there are boat tours available. It’s a perfect anchoring spot as Grayhound know.

Things are fairly mellow when the sun goes down. There are local joints where you’ll find live music, mostly soca and calypso.

Eating Out
Try the ‘catch of the day’ in most eateries, it’s as fresh as it gets. And don’t miss out on the roti, a local favourite.

You’ve got the oldest protected rainforest in the Western Hemisphere as a backdrop, and the beaches are stellar. If you’re up for it, there’s scuba diving and rainforest hiking.

Unique Features
What makes Castara Bay special is its untouched, authentic character. It’s a mix of stunning natural scenes and genuine community spirit that makes you feel like you’ve stumbled upon a hidden gem.

Castara Bay really is worth a visit, whether you’re a seasoned sailor or just someone looking to unwind.

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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