| Embark | Disembark | Vessel | Duration | Voyage No |
|---|---|---|---|---|
| Fri 23-01-2026, 19:00Antigua, Caribbean | Fri 30-01-2026, 10:00St Martin / St Maarten | Eye of the Wind | 7 Nights | EYE26/03 |
Trade the winter doldrums for a week of Caribbean magic. Set sail from Falmouth Harbour, Antigua, aboard ‘Eye of the Wind,’ meandering through the Lesser Antilles with a stop at St. Barth, and finally dropping anchor in Marigot, St Martin. Experience the perfect blend of peaceful days under sail and lively shore excursions, all against a backdrop of azure seas and tropical landscapes.

| 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.

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?
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.
Your first port of call on this sunny adventure is likely St Kitts. Along the way, keep your eyes peeled for frigate birds soaring high and dolphins frolicking in the bow wake. You’ll get a front-row seat to the Caribbean’s more rugged side, like the craggy cliffs of St. Kitts or the remote coral reefs teeming with colourful marine life.
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!

Your final port of call is Marigot, St Martin—a town with a Franco-Caribbean pulse. If you’re considering extending your stay, you won’t be short on choices. Consider a hike to Fort Louis for panoramic views of the island. Those inclined to sample the local flavours should pay a visit to the Marigot Market. Here you’ll find a medley of spices, fresh produce, and unique crafts.

January in the Caribbean offers ideal sailing conditions. Expect the wind to be easterly, with speeds ranging from 15 to 20 knots—ideal for sailing these traditional vessels. Sea conditions are usually moderate, making for a relatively comfortable journey even for those new to the sailing world. Always be prepared for conditions to change, however.
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.
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.
Sailing into St Martin / St Maarten offers breathtaking coastal vistas. Watch for Simpson Bay Lagoon and Tintamarre Island, both havens for marine life. The coastline boasts dramatic headlands, pristine beaches, and anchorages ideal for exploration.
St Martin is an island split between two nations—France and the Netherlands. The northern side, Saint-Martin, is a French overseas territory, while the southern part, Sint Maarten, is an autonomous country within the Kingdom of the Netherlands. Despite the border, movement between the two sides is unrestricted, giving the island a seamless blend of European and Caribbean influences.
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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