| Embark | Disembark | Vessel | Duration | Voyage No |
|---|---|---|---|---|
| Mon 29-12-2025, 19:00St George’s, Grenada | Thu 08-01-2026, 10:00Le Marin, Martinique | Eye of the Wind | 10 Nights | EYE25/40 |
With a mixture of green rainforests and fantastic beaches, the Antilles islands of Bequia, St Vincent and Saint Lucia are all top travel destinations. Saint Lucia with the famous volcanic cones, the Pitons, is an iconic symbol of the Caribbean. Adventurous days at sea alternate with varied shore excursions and swim stops. Evenings and nights are spent in lively harbours or in dreamy secluded anchorages.
All that, plus some suitably Caribbean-style celebrations to see in 2026!

| 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.

Tropical greenery, exotic markets, hospitable people, palm islands in turquoise waters… picture the Caribbean and you’re basically picturing the Grenadines. St George’s, the capital of the ‘Spice Isle’ is regarded as one of the most beautiful cities in the Antilles. A fine aroma wafts through the city when the nutmegs are roasted. We’d highly recommend taking some time before you board to explore this beautiful place.
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.

It doesn’t get any more Caribbean than this! Sail through turquoise blue water along the chain of southern Windward Isles. Bequia, Saint Vincent and Saint Lucia appear on the horizon one after the other, each offering their own shoreside adventures and chances to explore the local towns and villages.
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.
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!

The French overseas department of Martinique also bears the nickname “the flower island”. Don’t miss the opportunity to visit the rainforests of the North and maybe take some time to stretch your legs with a hike through the spectacular mountainous landscape.
Of course you might prefer to just put your feet up and try the local rum punch- supposedly the best in the Caribbean…

You’re in for a delightful Caribbean sailing adventure. During this time, you can expect warm temperatures averaging around 26-29°C (79-84°F) and calm seas. The trade winds usually blow from the northeast at 10-20 knots, creating ideal conditions for sailing. It’s worth noting that January falls within the dry season, so rain is less common. For first-time sailors, these conditions should provide a gentle introduction to the joys of sailing in the Caribbean.
On a sailing voyage we never guarantee a specific itinerary. Skippers will always be aiming for the best and safest sailing routes given the forecast. They are as keen as you to include all the potential highlights of a voyage, 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 is likely to be possible, based on past trips and prior experience, but nothing is guaranteed. 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.
St George’s, the lively capital of Grenada, is a picturesque harbour with plenty to keep an errant sailor occupied for a few days if you have some spare time! Tour Fort George to experience the island’s colonial history and visit the Grenada National Museum to learn about local culture. There are also plenty of beach parties and live music if you’re craving nightlife after some weeks at sea! For a leg stretch, the stunning Grand Anse Beach or the Grand Etang National Park are both glorious.
Le Marin, on the Southern tip of Martinique, boasts a rich history. Visit the Église Saint-Étienne, an 18th-century church overlooking the harbour. For more, explore nearby Fort-de-France and the Schoelcher Library, which highlights Martinique’s cultural evolution.
The town is a haven for food lovers. Try fresh seafood dishes such as grilled lobster, Creole curries, and accras (fried fish fritters).
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
Embark
Mon 22-12-2025
Bridgetown, Barbados
Disembark
Mon 29-12-2025
St George’s, Grenada
From
€2590
South America and the Caribbean OS230326
Embark
Mon 23-03-2026
Paramaribo, Suriname, South America
Disembark
Fri 03-04-2026
Le Marin, Martinique
Fully Booked
Martinique Caribbean Exploration OS040426
Embark
Sat 04-04-2026
Le Marin, Martinique
Disembark
Thu 16-04-2026
Le Marin, Martinique
From
€2940.00
Recently Viewed Voyages
Through the Hebrides and Across the North Sea SM050526 V17
Embark
Tue 05-05-2026
Dublin, Ireland
Disembark
Wed 13-05-2026
Bergen, Norway
From
€1280
New Year in the Windward Isles EYE25/40
Embark
Mon 29-12-2025
St George’s, Grenada
Disembark
Thu 08-01-2026
Le Marin, Martinique
From
€3700
Christmas on a 4-Masted Schooner SM231225 V48
Embark
Tue 23-12-2025
Funchal, Madeira
Disembark
Sun 28-12-2025
Funchal, Madeira
From
€1150