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Caribbean Treasures: Guadeloupe, Montserrat, Antigua

Berth Price

2 Berth Cabin En-Suite Price per person



Embark Disembark Vessel DurationVoyage No
Fri 02-02-2024, 19:00Pointe a Pitre, Guadeloupe Fri 09-02-2024, 10:00Antigua, Caribbean Eye of the Wind 7 NightsEYE24/06

This one-week voyage starts from Guadeloupe’s verdant landscapes and sets course for Montserrat’s volcanic vistas. Along the way, you’ll be treated to a smorgasbord of natural beauty, from leaping dolphins to sweeping seascapes. The journey concludes with a stay in Antigua, an island renowned for its abundant beaches and rich history. It’s a week of sailing that marries awe-inspiring views with authentic experiences.

  • Voyage
  • Vessel


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.


  • Just paradise at sea
  • En suite cabins & elegant interior
  • Good trade winds for exciting sailing
  • Sail in the Sun in February
  • Star gazing and dark skies

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

Tropical Fish The Caribbean on a Tall Ship Sailing Morgenster with Classic Sailing
trade wind sailing on Eye of the Wind


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.

Setting Sail from Guadeloupe

Casting off from Guadeloupe, the so-called “Butterfly Island,” feels like setting sail from a page ripped out of a storybook. Verdant hills kiss azure waters as the vessel heads for the open sea. Guadeloupe is a haven for nature lovers—its landscapes varied, its culture vibrant. As you crew hoists the sails, a sense of pure adventure fills the air. Here you’ll get an authentic introduction to the Caribbean way of life, surrounded by nature’s finest offerings. Before departure, take some time to revel in the island’s lush scenery and colourful marketplaces. It’s an ideal backdrop for what’s to come.

Along the Way

The course is set for Montserrat. If you haven’t had the chance to witness a volcanic island before, you’re in for a treat. Montserrat’s Soufrière Hills Volcano stands as a sentinel of Mother Nature’s unpredictability. The island serves up a good deal more than volcanoes, though—think lush, green hillsides and abundant birdlife. As the vessel tacks and jibes its way through Caribbean blue, keep an eye out for pods of dolphins and perhaps even a marlin making a bold appearance. It’s a course strewn with natural spectacles and historic landmarks, each worthy of a sea shanty or two.

palm trees and coconuts - caribbean beach landings
palm trees and coconuts – caribbean beach landings

Arriving in Antigua

When Antigua emerges on the horizon, it feels as if someone has taken a paintbrush to the sky, daubing it with the hues of paradise. You can’t miss Antigua’s beaches—365 of them, one for each day of the year, if you’re so inclined. Upon mooring, the island offers you its finest. For those considering an extra day, it’s not just about lazing on the beach. Antigua has historical depth; take a visit to Nelson’s Dockyard, the only continuously working Georgian dockyard in the world. For the more adventurous, a hike up to Shirley Heights gives you a panoramic view of the island that’s worth its weight in rum. And speaking of rum, why not round off the day with a tour of a local distillery? Treat your palate while recounting tales from the high seas.

caribbean landfall


In February, you can expect the trade winds to be your loyal companions. Usually blowing from the east-northeast, these winds make for excellent sailing conditions. Skies tend to be mostly clear with temperatures hovering around a pleasant 26-28°C (79-82°F). Seas are generally moderate, making it a sublime time for any sailor—novice or veteran—to feel the rhythm of the waves.


On a sailing voyage we never use the word itinerary, as skippers will always be aiming for the best and safest sailing routes for the forecast. They are as keen as you to include some of the highlights described above, but when it comes to sailing, you have to go with Mother Nature, not fight her. The description provided is based on what we think might be possible, based on past trips, or prior experience, but nothing is guaranteed on a sailing voyage. As such, the scheduled joining ports, routes, activities and/or destinations may be altered. Due to the complexities of weather systems, this may be at very short notice. 


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.

Start & End Port

Pointe a Pitre, Guadeloupe

Musée Saint-John Perse 002


Pointe a Pitre, Guadeloupe

How to Get There


From the UK and Europe: Direct flights from London and major European cities like Paris are your best bet. Once at Pointe-à-Pitre International Airport, taxis and car hire services are readily available. 


From North America: Direct and connecting flights are available from major U.S. and Canadian cities. You could also opt for a Caribbean cruise that stops in Guadeloupe.


From Australia: There are no direct flights, but you can easily connect through major airports like London, Paris, or New York. It’s a long journey but worth the trek.


What to Do in Pointe-à-Pitre


History: The Memorial ACTe museum is a standout, exploring the history of slavery and its impact. Also, the old part of the city, with its colonial architecture, gives you a feel of its historical background.


Culture: Local markets like the Spice Market are a sensory experience that showcases the island’s rich culture. Music festivals and local dances like the Gwo-Ka are worth checking out as well.


Sites of Interest to a Sailor: Guadeloupe’s coastline is quite a treat for any sailor. There are plenty of harbours, marinas, and sailing tours you can join. Bas-du-Fort Marina is a hub for sailors, fully equipped with all necessities.


Entertainment: The city comes alive at night with a variety of bars and clubs playing everything from jazz to local Caribbean tunes. Not into the bar scene? There are movie theatres and art galleries.


Eating Out: The food here is a blend of French and Creole cuisine. Don’t miss out on tasting local dishes like Bokit and Accras de Morue. Fresh seafood is an obvious choice, given the location.


Nature: Guadeloupe is not just about the beaches. It’s got splendid rainforests where you can hike or zipline. The Pointe des Chateaux is where you’ll see the Atlantic meet the Caribbean Sea, a sight you don’t want to miss.


Unique Features: What sets Pointe-à-Pitre apart is its mix of French and Caribbean culture, which you’ll see everywhere—from the language to the food. The scenic mix of rainforests and beaches also makes it unique.


Honestly, whether you’re looking to sail or just soak in some local culture, Pointe-à-Pitre is a must-visit. It offers a bit of everything, and you’d be hard-pressed to find a reason not to fall in love with this place.


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.


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

What to pack for a sailing holiday on the Eye of the Wind

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. 


A fabulous adventure! Words cannot convey the experience.

John, Tortola to Bermuda

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

F Coutreau

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!


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


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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