Voyage Filters

The full Atlantic Crossing

Best seller

Single Berth Per Person

Join Waiting List


Embark Disembark Vessel DurationVoyage No
Tue 12-12-2023, 14:00Portimão, Portugal Sun 28-01-2024, 11:00Castara Bay, Tobago Grayhound 47 NightsGR121223-A

Ready for a break from the hustle and bustle? Climb aboard an 18th-century-style Cornish Lugger for a trip of a lifetime. Start in the charming Portuguese city of Portimão and end in Castara Bay, Tobago.
No experience? No worries; you’ll learn all the ropes. Christmas and New Year’s will be celebrated in exotic locations like the Canary Islands and Cape Verde, filled with unforgettable nature and wildlife. The trip is an eye-opener, from watching the sun set into the ocean to gazing at the Milky Way, your digital detox starts here.

  • Voyage
  • Vessel


  • 47 nights at sea.
  • Disconnect on an 18th-century Cornish Lugger.
  • Learn celestial navigation and sailing basics.
  • Start in scenic Portimão, end in tranquil Castara Bay.
  • Celebrate Christmas in the Canary Islands.
  • New Year’s in picturesque Cape Verde.
  • Keep watch for whales, turtles and rare birds.
  • Tobago’s beaches and rainforests are worth extra days.


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. 


If you’re looking to really disconnect and find inner tranquillity, then look no further. Picture yourself aboard a Cornish Lugger, a replica of an 18th-century privateer. Navigating the Atlantic with celestial charts and a sextant, it’s a chance for total digital detox.

Our journey begins mid-December in Portimão, Portugal. This isn’t just any old port; it’s a coastal gem with beautiful beaches and a lively marina. If you can, arrive a few days early and enjoy some superb Portuguese seafood. 

We set sail to Madeira where we might anchor for a night or two, taking the opportunity to visit the islands of Porto Santo and Islas Desertas. It’s a good idea to stretch your legs here; the hiking trails and natural beauty are unmatched.

From there, it’s on to the Canary Islands, where we celebrate Christmas. They offer more than just sun; their volcanic landscapes and unique culture make for a fascinating visit. We’ll ring in the New Year in Cape Verde, a place of unparalleled natural beauty, where the beaches meet cliffs in a spectacle of nature’s finest.

Then comes the core Atlantic journey. We divide into night watch groups, keeping eyes peeled for everything from massive Albatrosses to whales and dolphins. Here you’ll fully understand what it’s like to be one with the ocean. 

After travelling 2200 Nm, we arrive at our final destination, Castara Bay in Tobago. This isn’t just a stop; it’s a destination in itself. We strongly recommend you book a stay in this sleepy fishing village. Get lost in the tropical rain forests, or relax on the white sandy beaches, greeted by the friendliest locals you’ll ever meet.

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

Portimão, Portugal

Portimão, PortugalHow to Get There

For those yearning for the vibrant mix of history, culture, and breathtaking landscapes, Portimão in Portugal’s Algarve region is a destination that doesn’t disappoint. Here’s a guide on how to reach this splendid town:

From the UK:

The most hassle-free method is to hop on a direct flight from numerous UK airports straight to Faro. Upon landing, Portimão is an hour’s drive away, or one can also opt for a train or bus journey.

From Europe:

For those driving from Spain or other European nations, the A22 highway will lead you directly to Portimão. Alternatively, the Iberian Peninsula offers picturesque rail journeys, although they tend to be lengthier.

From North America:

Direct flights are available from major cities to Lisbon. Once in Lisbon, a domestic flight to Faro or a relaxing train ride will bring you to Portimão.

From Australia:

Typically, travellers would first transit through major European hubs such as London, Madrid, or Lisbon, followed by a journey to Faro and subsequently to Portimão.


Parking can be a tad tricky during the bustling tourist season in Portimão. Those travelling by car might want to consider reserving parking spots in advance. The website JustPark ( can be particularly handy for this purpose.

What to Do in Portimão


Portimão has a treasure trove of historical landmarks. From the majestic Fort of Santa Catarina to the Museu de Portimão that once was a thriving canning factory, the town’s history is rich and varied.


Delve deep into Portimão’s cultural tapestry during its annual Sardine Festival, a testament to the region’s culinary and cultural heritage. The numerous art galleries scattered around town further offer a window into the souls of local artisans.

Sites of Interest to a Sailor:

With the serene Arade River meeting the Atlantic, sailors are in for a treat. The Portimão Marina, equipped with top-tier facilities, serves as an ideal base. Moreover, the sailing tours on offer promise unrivalled views of the Algarve coast.


As the sun sets, Portimão comes alive with its eclectic nightlife. From quaint beachside bars echoing with live music to swanky nightclubs, there’s something for everyone. Traditional Fado music venues are also scattered throughout, offering soulful Portuguese melodies.

Eating Out:

Seafood aficionados rejoice! With the Atlantic at its doorstep, Portimão serves up some of the freshest catches. A must-try is the town’s signature grilled sardines. Waterfront restaurants, dishing out both traditional and international cuisine, add to the dining experience.


Praia da Rocha, with its golden sands set against towering cliffs, is a paradise for beach lovers. Adventurous souls can explore the trails of the nearby Monchique Mountains, while water sports enthusiasts have a buffet of activities to choose from.

Unique Features:

What truly sets Portimão apart is its harmonious blend of old-world charm with modern comforts. The town’s cobbled pathways tell tales of yesteryears, while its contemporary marinas and amenities offer all the comforts of the 21st century.

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


Entire Cross Atlantic Adventure GR121223-A


Tue 12-12-2023

Portimão, Portugal


Sun 28-01-2024

Castara Bay, Tobago

lugger grayhound under full sail on a green sea. sail cargo voyages and adventure holidays with classic sailing

Fully Booked