| Embark | Disembark | Vessel | Duration | Voyage No |
|---|---|---|---|---|
| Fri 16-01-2026, 19:00Pointe a Pitre, Guadeloupe | Fri 23-01-2026, 10:00Antigua, Caribbean | Eye of the Wind | 7 Nights | EYE26/02 |
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.

| 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 |
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.

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.

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.

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?

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.
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. For more on this, see our article ‘What is a Hands-On Sailing Holiday?’
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.
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.
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.
Practical Advice for Eye of the Wind
Practical Advice for Covid 19 and Eye of the Wind
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.
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.
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
Celebrate Christmas Caribbean-style! EYE25/39
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