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Caribbean Exploration I – Tobago to St Lucia

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Tue 13-02-2024, 14:00Castara Bay, Tobago Sun 18-02-2024, 11:00Rodney Bay, Saint Lucia Grayhound 5 NightsGR130224

Join Grayhound for a memorable Caribbean sailing holiday from Tobago to St Lucia. Start at the laid-back Castara Bay in Tobago; it’s worth coming early to explore the island’s natural beauty. We’ll sail to Grenada, known for its spices and stunning snorkeling spots, in about 12 hours.

The adventure includes island-hopping, with highlights like Tobago Cays, and ends in Rodney Bay, St Lucia, where a final dinner awaits. 

  • Voyage
  • Vessel


Cast off from charming Castara Bay in Tobago.
Reach Grenada in 12 hours thanks to North East Trade Winds.
Immerse in Grenada’s spice-infused atmosphere and tropical hideaways.
Be part of the crew as we navigate north through St Vincent and the Grenadines.
Don’t miss Tobago Cays, a sailor’s and explorer’s dream.
End the voyage in Rodney Bay, St Lucia, the Land of the Iguanas.
Number of nights at sea: Variable depending on itinerary and stops.


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. 


Embark on a captivating Caribbean adventure aboard Grayhound, our classic privateer sailing ship, as we set sail from Tobago to St Lucia. Starting at the idyllic Castara Bay in Tobago, you won’t want to miss the island’s untouched nature and tranquil beaches. The locals are friendly, and the vibe is authentically Caribbean; it’s well worth arriving a few days early to soak it all in. 

Setting sail, we’ll catch the North East Trade Winds, making our way to Grenada in about 12 hours. Known as the “Isle of Spice,” Grenada is a feast for the senses with its nutmeg aroma and lush rainforests. The azure blue anchorages are not just beautiful; they are also a paradise for diving and snorkeling. 

From there, we journey north, hopping from island to island through St Vincent and the Grenadines and the Windward Islands. You’ll have a say in the route, giving you a sense of shared ownership in our sailing adventure. One of the highlights will undoubtedly be Tobago Cays, a collection of over 100 islands considered among the best for sailing and exploration globally. 

Before we reach our final stop in Rodney Bay, St Lucia, also known as the “Land of the Iguanas,” we’ll circumnavigate the volcanic island of Saint Vincent. Its active volcano, La Soufriere, is a sight to behold. At Rodney Bay, be prepared for a gastronomic journey as we go market hunting for exotic fruits like papayas and mangoes with our ship’s cook. A final dinner and some local rum drinks ashore will cap off a holiday you won’t soon forget.

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

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.

Rodney Bay, Saint Lucia

Rodney Bay on Saint Lucia

Crystal clear Caribbean Sea, Reduit beach, Rodney Bay in St Lucia. Taken from Fort Rodney on Pigeon Island National Historic ParkRodney Bay St Lucia

How to Get There

Flying is the most straightforward way to reach Rodney Bay, Saint Lucia, especially for travellers from places like the UK, Europe, North America, and Australia. Most international flights land at Hewanorra International Airport in Vieux Fort, located at the southern tip of the island. From there, you can either hire a car or take a taxi for the roughly 1.5-hour drive to Rodney Bay. For those coming from neighbouring Caribbean islands, arriving by ferry is also an option. Trains and coaches aren’t available for international travellers as Saint Lucia doesn’t have those types of networks.

What to Do in Rodney Bay


Rodney Bay has a rich naval history, particularly thanks to its strategic harbour. A must-visit spot is Pigeon Island, now a national park, where you’ll find remnants of naval forts and various artefacts.


The local culture here is a mix of Afro-Caribbean, French, and British influences. You’ll often hear Calypso music in the background, and local crafts are popular. The Saint Lucia Jazz Festival in May is often hosted in Rodney Bay and is a cultural highlight.

Sites of Interest to a Sailor

For sailors, Rodney Bay is a bit of paradise. The bay itself serves as a natural harbour, and there’s a fully equipped marina. Whether you’re sailing traditional boats or tall ships, you’ll find the facilities and views here top-notch. Sailing tours to explore nearby islands are also available.


As far as entertainment goes, Rodney Bay is the island’s go-to spot for nightlife. There are numerous bars and clubs, often with live music, particularly on weekends.

Eating Out

If you’re a foodie, Rodney Bay won’t disappoint. Seafood is the star of the show, but there’s also a good range of international cuisines. For a true taste of Saint Lucia, try the ‘St Lucia Seafood Friday’ event in Anse La Raye.


Don’t forget that Saint Lucia is not all about the sea. The island’s interior is lush with rainforests, and a visit to the iconic Piton Mountains is highly recommended. There are plenty of trails for hiking and natural waterfalls where you can cool off.

Unique Features

What makes Rodney Bay special is its blend of modern amenities with traditional Caribbean elements. The natural harbour makes it ideal for all kinds of sailing, and its historical context adds a layer of depth to your visit. Add to this the vibrant nightlife, and you have a destination that caters to a broad range of interests.

Rodney Bay is a well-rounded destination, whether you’re an old sea dog or just someone looking to soak in a variety of experiences.

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.

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.

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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