Voyage Filters

Cape Verde & Trans Atlantic passage

Book your bunk

Single Berth Per Person

Last Place!


Embark Disembark Vessel DurationVoyage No
Wed 27-12-2023, 14:00Santa Cruz de la Palma, Las Palmas Sun 28-01-2024, 11:00Castara Bay, Tobago Grayhound 32 NightsGR271223-A

Embark on a unique sailing journey from the Canary Islands to Tobago on Grayhound. This voyage offers a perfect digital detox, as you sail through the Atlantic practicing celestial navigation. Start off exploring the Canary Islands, stopover in the picturesque Cape Verde, and finally anchor in Tobago’s Bay of Castara.
No prior sailing experience needed; the crew will train you.
Take extra time at both ends of your journey, you won’t regret it.

  • Voyage
  • Vessel


  • Start from the Canary Islands, a hotspot for adventurers.
  • Sail to Cape Verde, about 600 Nautical Miles west of Senegal.
  • New to sailing? We’ll teach you everything.
  • Number of nights at sea: 32
  • Keep an eye out for humpback whales and dolphins.
  • Final stop: Tobago’s Bay of Castara.
  • Consider booking a bungalow for an extended stay.


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 are 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. 


Get ready for a proper passage adventure that takes you from the Canary Islands to Tobago aboard Grayhound, a Cornish Lugger. The journey offers an ideal digital detox, away from the buzzing of phones and the glare of screens. Instead, we’ll be enveloped by nature’s expanse, guided by celestial bodies across the Atlantic.

Your adventure starts from the Canary Islands, a treasure trove of experiences. Apart from the stunning beaches, the islands offer everything from hiking on volcanic landscapes to exploring historical sites. Trust me, it’s worth taking an extra few days to soak it all in.

Our first stop is Cape Verde, located about 600 Nautical Miles west of Senegal. Imagine, if you will, landing just in time for a New Year’s celebration; now that would be unforgettable. The islands are a marvel for any lover of the sea, with a mix of tropical landscapes, unspoiled beaches, volcanic hills, and rich coral reefs. You can even spot sea turtles, humpback whales, flying fish, and tuna if you’re keen-eyed.

Now, as for the sailing itself, prior experience is a non-issue. Our skilled crew will teach you the ropes of operating a traditional Cornish Lugger. Whether it’s steering, sail hoisting, or celestial navigation, you’ll get hands-on experience.

Finally, we approach Tobago. Once we’ve cleared customs in Scarborough, we’ll anchor in the Bay of Castara, a small, quiet fishing village that serves as our final stop. The island is a paradise with its lush rainforests, deserted beaches, and friendly locals. Honestly, do yourself a favour and book a bungalow in advance to enjoy a few extra days here. Tobago is not just a destination, it’s an experience that stays with you.

You will learn how to sail a traditional Cornish Lugger. Whether you are an experienced sailor or not there is plenty to learn. Professional sailors are always surprised by Grayhound’s combination of sturdiness and sensitivity to the wind. She is nimble! There’s no limit to what you can learn about navigation and traditional sailing.

The Irish Sea is beautiful, mysterious and rich in history. We may find anchorages in Ireland or Wales, before setting a course for Land’s End. Grayhound was built in Cornwall from Cornish oak, so when she rounds Land’s End she’ll be giving a nod to her birthplace. Depending on the forecast, Grayhound might make a stop on the South Coast of Cornwall to restock and recharge before the final channel crossing to Douarnenez.


On a sailing voyage we never use the word itinerary, as skippers will always be aiming for the best sailing and shore landings for the forecast. This is a passage-making voyage, however, so there will be a need to make up the miles, and that can mean sailing in slightly stiffer conditions than on a round trip. The Irish Sea and English Channel can both get a little punchy, but Grayhound is a solid seagoing ship and will take good care of you.


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.

Irish coast at sunset. Photo Pixabay

Start & End Port

Santa Cruz de la Palma, Las Palmas

Santa Cruz de la Palma, Las Palmas

How to Get There

Santa Cruz de la Palma in Las Palmas isn’t as tricky to get to as you might think, whether you’re jetting in from the UK, Europe, North America, or Australia. If you’re flying from the UK or Europe, you’ll find direct flights to La Palma Airport. From North America and Australia, you’ll likely need to catch a connecting flight via Madrid or another major European city. Once you’re at the airport, taxis and buses are available to get you into the town centre.

For those who fancy a bit of sea travel, ferries do run from other Canary Islands like Tenerife. Trains and coaches aren’t really an option here, given it’s an island. If you’re travelling by car, rental options are available at the airport and in the town.

What to Do in Santa Cruz de la Palma in Las Palmas

If you’ve got a soft spot for history, Santa Cruz de la Palma won’t disappoint. Make a point of visiting the Naval Museum, housed in a replica of Christopher Columbus’s ship. Then there’s the Insular Museum for a broader view of the island’s history.

As for culture, look out for local festivals. The Bajada de la Virgen is a must-see, taking place every five years. Traditional Canarian music and dance are always a part of local festivities, giving you a real taste of the culture.

Sites of Interest to a Sailor
It’s a great jumping-off point for sailing around the Canary Islands. The coastal views are spectacular, to say the least. It is a favourite Christmas meeting point for Tall Ships from Europe.

Nightlife here is more laid-back than rowdy. You’ll find a few bars with live music and traditional Canarian fare. If you fancy a dance, there are places for that too, but don’t expect large nightclubs.

Eating Out
You can’t visit Santa Cruz without trying the local cuisine. Fresh seafood is the name of the game here. Whether it’s a cosy tavern or a more upmarket restaurant, the grilled fish is usually a good shout. Also, try “papas arrugadas,” a local potato dish.

This island offers more than just beaches. There’s the Caldera de Taburiente National Park for starters, a must-visit for any nature enthusiast. Lush forests, hiking trails, and the occasional waterfall make this a stunning backdrop for outdoor activities.

Unique Features
Santa Cruz de la Palma is a blend of traditional Canarian architecture, cobblestone streets, and natural beauty that’s second to none. It’s less touristy than other Canary Islands, offering a more authentic experience. Take a walk down Calle Real, the city’s main street, and you’ll feel like you’ve stepped back in time.

In summary, Santa Cruz de la Palma offers something for everyone, whether you’re keen on history, looking to soak up some culture, or eager to get out on the water. It’s a place that doesn’t make you choose between land and sea; you get the best of both worlds.

Special Interests
If you have a special interest that you would like to find out about for this port or to tell us about, we would love to hear from you.

Sustainable Travel Carbon Offset Schemes

By selecting sustainable travel options and actively participating in carbon offset initiatives, you can make a positive impact while journeying to or from your voyage.
Here are some suggestions for carbon offset websites.

UK: One popular carbon offset website in the UK is “Clear” who offer a range of carbon offset projects and solutions for individuals, businesses, and organisations. They provide detailed information about their projects and allow users to calculate and offset their carbon footprint online.
North America: In North America, “Terrapass” is a well-known carbon offset website. Terrapass offers carbon offset projects across the United States and Canada. They provide options for individuals, businesses, and events to calculate and offset their carbon emissions. Terrapass also offers additional resources and information on sustainable living.

Europe: A popular carbon offset website in Europe is “MyClimate.” MyClimate provides carbon offset projects and solutions for individuals, businesses, and travel. They offer a carbon footprint calculator and allow users to support various sustainable projects worldwide. MyClimate focuses on promoting climate protection and sustainability.

Australia: “Greenfleet” is a prominent carbon offset website in Australia. Greenfleet focuses on planting native forests to offset carbon emissions. They offer individuals and businesses the opportunity to calculate and offset their carbon footprint by contributing to tree planting projects across Australia. Greenfleet provides detailed information about their projects and the positive environmental impacts they create.

Please note that these carbon offset websites may vary over time, so it is recommended to research and explore multiple options to find the most suitable one for your needs.

If any of these links do not work it would be kind of you to inform us, many thanks.

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.



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.

Other Voyages


Delivery voyage Iceland to Ullapool TC171023


Tue 17-10-2023

Reykjavik, Iceland


Fri 27-10-2023

Ullapool, Scotland

Sailing Holidays on Tecla with Classic Sailing

Fully Booked

Eye of the Wind

Epic Trans Atlantic Voyage: Tenerife to Barbados EYE23/41


Tue 21-11-2023

Santa Cruz, Tenerife


Thu 21-12-2023

Bridgetown, Barbados

Eye of the Wind under full sail. Adventure sailing holidays across oceans with classic sailing.

Fully Booked


Sail South to Sunny Tenerife TC311023


Tue 31-10-2023

Ullapool, Scotland


Fri 17-11-2023

Santa Cruz, Tenerife



Recently Viewed Voyages


Cape Verde & Trans Atlantic passage GR271223-A


Wed 27-12-2023

Santa Cruz de la Palma, Las Palmas


Sun 28-01-2024

Castara Bay, Tobago

Limited Spaces Available Grayhound with Classic Sailing