More

Voyage Filters

Caribbean Treasures: Guadeloupe, Montserrat, Antigua

Book your bunk

2 Berth En-Suite Cabin (price per person)

Available

€2590

Embark Disembark Vessel DurationVoyage No
Fri 16-01-2026, 19:00Pointe a Pitre, Guadeloupe Fri 23-01-2026, 10:00Antigua, Caribbean Eye of the Wind 7 NightsEYE26/02

Sail along the invisible border between the Caribbean Sea and the endlessly wide North Atlantic. Two of the most beautiful and lively Antilles Islands mark the start and finish points of this trip: Guadeloupe and Antigua. Expect days of exciting sailing interspersed with adventures ashore, walking through stunning landscapes and soaking up the lively Caribbean culture.

  • Voyage
  • Vessel

VOYAGE HIGHLIGHTS

  • Paradise at sea
  • Relax in good company
  • Visit unique islands
  • Good trade winds for exciting sailing
  • Star gazing and dark skies
  • Soak up some winter sun!

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

IDEAL VOYAGE FOR…

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.

Tropical Fish The Caribbean on a Tall Ship Sailing Morgenster with Classic Sailing

FULL VOYAGE DESCRIPTION

Setting Sail from Guadeloupe

It’s well worth taking some time on Guadeloupe before joining the ship, as there is a lot to see. Top of our list of recommendations would be the National Park- the largest in the Caribbean. It’s home to the highest waterfalls in the Antilles, a treetop path, mysterious mangrove forests and a lush flora and fauna to discover. 

Stepping aboard Eye of the Wind, you’ll get to know your fellow crew over dinner and receive a full safety briefing, plus an up to date itinerary based on the latest weather forecast.

Along the Way

Before Antigua, Eye of the Wind sets a course for Montserrat, with the striking Soufrière Hills Volcano at its heart. The island serves up a good deal more than volcanoes, though—think lush, green hillsides and abundant birdlife.

In between gorgeous shore stops, you’ve got reliable trade winds for some exciting sailing, plus a friendly and welcoming crew to show you the ropes! Keep an eye out for dolphins, marlin, pilot whales and turtles.

Arriving in Antigua

For those considering an extra day or two in Antigua, it’s not just about lazing on the beach (although with 365 beaches there is plenty of lazing to be done!). 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?

palm trees and coconuts - caribbean beach landings

WINDS, WAVES & WEATHER

In January, 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.

A NOTE ON VOYAGE DESCRIPTIONS

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. 

HANDS ON HOLIDAYS

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. For more on this, see our article ‘What is a Hands-On Sailing Holiday?’

SAILING STYLE & LIFE ON BOARD

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

 

Pointe-à-Pitre offers a lively blend of French and Creole culture and cuisine. Don’t miss out on tasting local dishes like Bokit and Accras de Morue. Fresh seafood is an obvious choice, given the location.

 

 

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 

Electricity

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. 

Review

Hello all at Classic

The trip went very well and was a great experience.

Everything was very well done, great captain, crew and guests.

Sea shanty singing lead by Matthew from the King's Pond Shantymen!

Best wishes, Bob. Eye of the Wind, Cadiz to the Canary Islands November 2024

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!

Andrea

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

COMPETENT and KIND

And such a beautiful ship. Thank you beyond measure

Susan

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. 

Other Voyages

Eye of the Wind

Celebrate Christmas Caribbean-style! EYE25/39

Embark

Mon 22-12-2025

Bridgetown, Barbados

Disembark

Mon 29-12-2025

St George’s, Grenada

Limited Spaces Available Sundowners on the deck of tall ship Eye of the Wind

From

€2590

Oosterschelde

South America and the Caribbean OS230326

Embark

Mon 23-03-2026

Paramaribo, Suriname, South America

Disembark

Fri 03-04-2026

Le Marin, Martinique

Sail on Oosterschelde with Classic Sailing

Fully Booked

Oosterschelde

Martinique Caribbean Exploration OS040426

Embark

Sat 04-04-2026

Le Marin, Martinique

Disembark

Thu 16-04-2026

Le Marin, Martinique

Limited Spaces Available Sail on Oosterschelde with Classic Sailing

From

€2940.00

Recently Viewed Voyages

Eye of the Wind

A Week Exploring the Leeward Isles EYE26/04

Embark

Fri 30-01-2026

St Martin / St Maarten

Disembark

Fri 06-02-2026

Pointe a Pitre, Guadeloupe

From

€2590

Eye of the Wind

Winter Sun in the Leeward Isles EYE26/02

Embark

Fri 16-01-2026

Pointe a Pitre, Guadeloupe

Disembark

Fri 23-01-2026

Antigua, Caribbean

From

€2590