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Embark Disembark Vessel DurationVoyage No
Fri 12-01-2024, 14:00Mindelo, Cape Verde Sun 28-01-2024, 11:00Castara Bay, Tobago Grayhound 16 NightsGR120124

Kick off this unforgettable sailing trip from Cape Verde, an island gem filled with culture and scenic spots. Learn Celestial Navigation using a sextant, and be hands-on crew members as we sail to Tobago. Enjoy a tranquil life at sea, spotting dolphins and albatross, and feel the daily grind vanish.

On arrival, clear customs in Scarborough before we head around the island and anchor in Castara Bay. This is a truly unique unspoilt village and you should consider spending a week exploring Tobago’s beaches and forests from here. 

  • Voyage
  • Vessel


  • Set off on an adventure across the Atlantic
  • Learn to navigate using the sun and stars.
  • Hands-on sailing experience, no expertise required.
  • Endless ocean views to help you forget life’s stresses.
  • Watch for marine life like dolphins, flying fish and frigate birds near coasts
  • Land in Tobago, clear customs, then anchor in a hidden gem, Castara Bay.
  • Consider a week’s stay to explore Tobago’s natural beauty.


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. 


Set sail on a life-altering long-distance sailing adventure across the Atlantic, from Cape Verde to Tobago in the Caribbean. In Cape Verde, you’re not just setting sail; you’re stepping away from a country rich in culture and landscapes. From its music scene to its stunning beaches, you might want to spend a couple of extra days soaking it all in before setting off.

Once onboard, we’ll dive into the basics of Celestial Navigation. Bring out the sextant and we’ll teach you how to chart a course using the sun, stars, and the old seafarer’s know-how. This is hands-on sailing, no armchair adventurers here. 

Beyond learning the ropes, you’ll be submerged in the sheer joy of life at sea. Each day the sun will rise and set in a panoramic ocean display, giving you the chance to witness marine life like dolphins, flying fish, and even the majestic albatross. The horizon will become your constant companion, and with each day, you’ll feel the stresses of modern life receding like a wake behind you.

When we approach Tobago, roughly 2200 Nm later, you’ll be a different person, humbled by the sheer majesty of the ocean and the sky. Once we dock in Scarborough and sort out the customs, we’ll take you around the island to the Bay of Castara, a secluded haven that rounds off this adventure perfectly. We highly recommend you book yourself a bungalow apartment in this charming fishing village. Take a week to explore Tobago; it’s a little slice of paradise, with white sand beaches, lush tropical rainforests, and locals who embody the true meaning of hospitality.

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

Mindelo, Cape Verde

Mindelo from the sea Free image

How to Get There

Flying is the most direct way to get to Mindelo on São Vicente Island. The island’s own Cesária Évora Airport is your destination if you can find a direct flight from some European cities. If you’re coming from the UK, Europe, North America, or Australia, you’ll probably have a stop in Lisbon or another European city. 

Another travel option is to fly into Sal Island’s Amílcar Cabral International Airport and then take an internal flight to Mindelo. Many European Holiday companies use Sal making very reasonably priced flights. 

Once you’re on the ground, you can easily get into town by taxi or local bus. 

If you’re the adventurous type, consider taking a ferry from another Cape Verdean island.

What to Do in Mindelo


Mindelo offers a glimpse into history with landmarks like the Torre de Belém, a scaled-down replica of the tower in Lisbon. There are also various old colonial buildings that provide a window into the island’s past.


The city is often called the cultural capital of Cape Verde and for good reason. Carnival in February is particularly colourful and lively, filled with music and dance.

Sites of Interest to a Sailor

If you’re into sailing, Mindelo has a deep-water port and marina that have served as a launching pad for tall ships bound for the Caribbean and North America. The port’s history dates back to when Cape Verde was an important coaling station, making it an intriguing place for anyone keen on maritime history. Today’s Marina Mindelo is well-equipped for modern sailors, and you’ll find stunning coastal views as you navigate the local waters.

Santo Antão. 

Well worth a day of your holiday.

This is a ferry from Mindelo to the island of Santo Antão that takes about an hour. 

Walking in Santo Antão is a real treat for nature lovers. The island is a paradise of rugged landscapes, steep cliffs, and lush valleys. The trails wind through terraced fields, past small villages, and into the heart of the island’s tropical forests. Whether you’re a seasoned hiker or just someone looking to soak up natural beauty, the trekking options here range from gentle walks to challenging hikes. 

The famous Ribeira da Torre and Paúl Valley walks are particularly worth your time. The dramatic scenery changes from arid flatlands to lush green hills, making every step an experience. All in all, it’s a hiker’s dream with views that you’ll remember long after you’ve returned home. 

Been there, done that and would do it again.


Market and Town Hall

The Town Hall has been converted for occasional exhibition space. An exhibition of African tribal artefacts from doors, to helmets, clothing and tools I saw was first class.

There is a large Municipal Market which is a great place to get a flavour of the island.



Mindelo offers a solid nightlife with plenty of bars and clubs, especially if you enjoy live music. Musical styles range from traditional morna to the more upbeat coladeira and funaná.

Eating Out

The local food scene is rich with options. Seafood is plentiful, and you shouldn’t leave without trying Cachupa, a hearty local stew that can include fish, meat, or both.



São Vicente isn’t the lushest of the Cape Verde islands, where you can find spots of natural beauty. Monte Verde offers hiking opportunities, and beaches like Praia da Laginha are perfect for relaxation.

Unique Features

What makes Mindelo special is its combination of cultural richness and maritime history. It’s not just a stopover but a place that offers both modern comforts and a sense of history that adds depth to your visit. Particularly for sailors, the mix of maritime legacy and modern facilities make Mindelo more than just another port—it’s a destination.

Mindelo is a gem of a destination, worth every effort to get there.

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.

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