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Leeward Islands via French Caribbean to Antigua.

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2 Berth Ensuite Cabin Per person

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Embark Disembark Vessel DurationVoyage No
Fri 20-01-2023, 19:00Pointe a Pitre, Guadeloupe Fri 27-01-2023, 10:00Antigua, Caribbean Eye of the Wind 7 NightsEYE23/04

Eye of the Wind, we will take you on an island hopping journey southwards from leeward to windward island groups. Travelling with the wind and human power, steering by big ships wheel under bright stars, and climbing the rigging to check the route through the coral reef offers a way of exploring the Caribbean that has been unchanged for centuries. Breathtaking natural landscapes, sailing adventures in tropical blue skies with brisk trade winds is a sailors idea of heaven. An unusual detour to the island Montserrat, with its recently active volcano, is planned en route.

  • Voyage
  • Vessel


  • Island hopping to some of the most scenic beaches and coves of the Caribbean
  • Across the Caribbean Sea aboard a windjammer with a young and friendly crew
  • Attractive ports of embarkation and debarkation: Antigua and Guadeloupe
  • Active sailing and manoeuvering on a 100-year-old tall ship … feel free to participate!
  • The grandeur of the ocean and its wildlife
  • Caribbean flair ashore
  • Excellent onboard cuisine, delicious meals from morning to evening

Eye of the Wind

Sailing Areas New Zealand
Vessel type / Rig 2 Masted Brig
Guest Berths 12
Beam 7.01m (23ft)
Draft 2.7m (8.9ft)
Overall Length 40.23m (132ft)
Year Built 1911
More about the Vessel

Voyage Description


Romantics, solo travellers, sun lovers, sailors and novices who want to see the Caribbean as working crew on a square rigger. Feel less like a tourist and experience island life as a sailor. No experience is needed as the professional crew will teach you to find buntlines and braces, clewlines and yard halliards. If you would rather be outdoors and active this winter and feel the wind in your hair then sign up before the mast. Eye of the wind is a sail training ship, but there is no deck scrubbing (unless you like the exercise). Guest crew can dip into the exciting stuff and not feel guilty resorting to the mattresses on the sun deck when there are enough volunteers to set a sail or take a turn on the helm.


  • Island hopping to some of the most scenic beaches and coves of the Caribbean
  • Across the Caribbean Sea aboard a windjammer with a young and friendly crew
  • Attractive ports of embarkation and debarkation:  Guadeloupe and Antigua
  • Active sailing and manoeuvering on a 100-year-old tall ship … feel free to participate!
  • The grandeur of the ocean and its wildlife 
  • Caribbean flair ashore
  • Excellent onboard cuisine, delicious meals from morning to evening
January 2019 Winner - Carol Van Dellen-Viggars Photo on Morgenster in the Caribbean
sailing in the Caribbean


Guadeloupe – blend of cultures

For nature lovers, Guadeloupe – the Emerald Island – is a green paradise where you can discover the largest national park in the Caribbean with the highest waterfalls of the Antilles, a treetop path, mysterious mangrove forests, and a lush plant and animal life. Embarkation is at 19.00 in the port town of Pointe-à-Pitre, Afterwards, there will be dinner together in the comfortable lounge, where you will quickly feel at home on the Eye of the Wind’s deck and soon get to know your fellow sailors. From the Eye of the Wind’s deck, we will have a breathtaking view of the almost 1,500 metres high volcanic cone of La Soufrière, and will round off the day by watching the stunning sunset.

The butterfly-shaped island of Guadeloupe is influenced largely by French, African, as well as East and West Indian cultures. This mix is especially evident in the architecture, which ranges from the French colonial style to the Hindu temple. Be enchanted by a fascinating blend of exotic smells. The cuisine of the Antilles is characterised by fruits, spices, coconuts and seafood of all kinds.We will drop anchor again in the small bay of Deshaies. On the west coast of Guadeloupe, we will be situated in a quiet and scenic location, from where you can start to discover the island. Besides wide sandy beaches, there are also a botanical garden, walking trails through the hilly landscape, and maybe even one or two cocktails in one of the countless bars.

rope bridges and waterfalls in the jungle
rope bridges and waterfalls in the jungle

Antigua – home of Classic Yacht Racing

You will make your final landfall at Falmouth Harbour, a natural horseshoe shaped bay on the sugarcane island of Antigua. The breathtaking sunset is the highlight of a romantic evening stroll, but you can see it from the deck of a square rigger. Disembarkation is at 10.00, and after a hearty breakfast on board you will be raring to go and explore the island. 

The former British colony is not only famous for the annual Antigua Sailing Week, one of the most important regattas in the world, but also for its 365 dream beaches. After being discovered by Christopher Columbus, the settlement of the island was shaped by British colonial rule, which lasted around 350 years. The British Naval Fleet was based here and English harbour was one of the best hurricane holes to shelter in. Today instead of men o war careening their ships bottoms, or loading cannons, tourists enjoy restaurants in the old stone warehouse buildings and watch the pelicans diving into the harbour.

trade wind sailing on Eye of the Wind
trade wind sailing on Eye of the Wind

Our sailing waters: Sail from the French Caribbean to Antigua

The Eye of the Wind is not a ship that likes to lie idle in the harbour, so it is time to cast off the lines the next day. After receiving safety instructions and an introduction to sailing by the ship’s crew, you will soon be able to take part in sailing yourself – no previous knowledge is required. We will set course for Antigua, exploring Guadeloupe’s neighbouring islands in the Caribbean Sea. You will get to know the Eye of the Wind as a seaworthy and reliable ship that has proven itself in all weather conditions. You can help actively with the sailing manoeuvres or just relax and watch. The setting and trimming of the sails during the days at sea will become an ever more fascinating spectacle from a long gone seafaring era.

Island hopping, anchorages & time ashore

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 and most idyllic or sheltered anchors and ports. They are as keen as you to include some of the highlights described below, but you have to go with Mother Nature, not fight her. Where the ship goes ashore depends on the wind and weather conditions, and is decided at short notice by the captain, who will take your wishes into account whenever possible. This ensures that your sailing trip is a pleasant mix of adventure, relaxation, active participation and pure enjoyment.

Around Guadeloupe there are smaller islands – each with their unique character like La Desirade. Terre de Bas, Marie Galante.

Between Guadeloupe and Antigua is the island of Monserratt. The islanders were evacuated from here due to the volcano erupting, and there are various active submarine volcanoes near here so you may just be sailing by…..

Either side of Antigua you have Barbuda to the East and Nevis to the West, which might feature as a quick stop or a swim at anchor. Barbuda is surrounded by shallow seas and turquoise waters and feels very remote, like a proper Robinson Crusoe desert island.


The Real Pirates of the Caribbean – Lush rainforests, mountains and waterfalls

There are few things which beat a tropical sunset below the yard-arm whilst at anchor in a timeless setting. A sailing ship as your base gives you access to the unspoilt Caribbean; Fishing villages where the chickens roam the shore, or landing like an early explorer on a remote beach anchorage under a forest covered volcanic peak. 

If you have been dazzled by the natural scenery in the ‘Pirates of the Caribbean’ movies then both Guadaloupe and Dominica are much closer to that lush volcanic island paradise than more well known Caribbean tourism locations.  The second movie ‘Dead Mans Chest’ and 3rd Capt Jack Sparrow adventure At ‘World’s End’ were filmed in the rainforests of Dominica, close to Guadaloupe.

caribbean landfall
caribbean landfall


Average air temperatures in Guadeloupe are 26-28 degrees centigrade. Sea temperatures are a balmy 26-28 degrees.

If you are on the Atlantic ocean side of Caribean islands the seas can be boisterous and blue. In the lee of any big volcanic island or inside a protecting reef, the seas can be flat. The winds mixed with tropical sun are generally the reason why the Caribbean is a perfect sailing ground. Square riggers under full sail, generally create some shade somewhere on deck or in the rigging so you can always find a cool spot. There is air conditioning in the cabins.


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.


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.

Eye of the wind - big ships wheel
Eye of the wind – big ships wheel


Every customer sailing with us will need to fill in basic medical questions on their booking application. If you are not sure if your current level of fitness and agility are up to a voyage, then please ring the Classic Sailing Office on 01326 53 1234 and we can chat through your concerns and possibly find options that might suit you better.

Start & End Port

Pointe a Pitre, Guadeloupe


Antigua, Caribbean

Classic Sailing vessels generally use either Falmouth Harbour or English Harbour in Antigua for crew changes. Both harbours are in the SW of the island and virtually next door to each other. The ships operators will send your joining details once they have a berth confirmed by the harbour authorities, but both locations are a great place to start or finish your sailing holiday.

Kit List

Working Language on Board is German and English

Practical Advice for Eye of the Wind   

Practical Advice for Covid 19 and Eye of the Wind

What is Included

  • Sailing Instruction
  • All meals to include refreshments throughout the day
  • Duvet, pillow and sheets
  • Hand towels

What is not Included

  • Waterproof jackets and trousers
  • Alcoholic drinks but there is a bar on board
  • Any entry visas required

What to Bring

Suitcases take up a lot of room in a cabin, so it is better to uses soft bags in a ship. A small rucksack for going ashore is useful.

  • Eye of the Wind does not supply waterproof jackets and salopette type trousers. Please bring your own waterproof clothing.
  • A mix of warm and wind proof clothing.
  • Lots of thin layers is better than one thick layer in cold destinations.
  • In tropical countries - long sleeves and long trousers to protect you from the sun
  • Footwear on board needs a good grip and soft soles- the decks are wood or steel.
  • Ashore stout, waterproof walking boots are best if you are in remote places.
  • Eye of the Wind has electric sockets in all the cabins 240 V 
  • Cameras, spare batteries, chargers if you need them
  • Binoculars are handy for bird watching etc.
  • Suntan lotion, hats, sunglasses
  • Dont forget any regular medication, persciption glasses and spare
  • Euros for bar bill 
  • Passport, travel insurance, tickets etc
  •  To get ashore is usually by dinghy so be prepared to get wet feet. Rubber boots or quick drying sandals - depending on the location.
  • The ship provides hand towels but please bring a beach towel
  • snorkel and mask for caribbean if you like snorkelling (travel tip: swimming goggles pack up smaller than a facemask)
  • Bring insect repellant for Caribbean as can get mosquitos ashore in evening (rare at anchor)
  • ear plugs can be handy 


All the power to your plug sockets comes from the ship's generator which runs on deisel. The less the generators have to run to top up power, the nicer it is for the guests on board and also greener for the planet. Please don't bring loads of hairdriers, electric devices to charge.

There is no internet on board whilst at sea. 


Eye of the Wind is an experienced operator with many happy customers. She sails in Northern Europa nad the Baltic in Summer (Northern Hemisphere) and across the Atlantice to the Caribbean for some winter sunshine sailing holidays.

Facebook Reviews currently 5 out of 5 stars 


Tortola to the Azores! What a great time. Thanks to Captain Pit and the crew. An awesome adventure with awesome people!" F Coutreau, New England


What a wonderful, lovely, great, awesome trip we've had from Malaga to Lanzarote! I loved and enjoyed every minute.

Thanks again for this wonderful experience. I miss you guys! Andrea Schwartz

Dear Adam,

Now that was a voyage! The EYE crew - all 10 - five women and five men - embody two words:


And such a beautiful ship.

Thank you beyond measure, Susan.

Eye of the Wind Faroes to Iceland Summer 2022

Vessel Gallery

With red sails against a blue sky, Eye of the Wind is a photogenic ship. If you have any new images we would love to see them since Eye of the Wind has only recently returned to our website. 

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