| Embark | Disembark | Vessel | Duration | Voyage No |
|---|---|---|---|---|
| Fri 30-01-2026, 19:00St Martin / St Maarten | Fri 06-02-2026, 10:00Pointe a Pitre, Guadeloupe | Eye of the Wind | 7 Nights | EYE26/04 |
Trade the winter doldrums for a week of Caribbean magic. This trip from Marigot, Saint Martin to Guadeloupe offers the chance to explore some gems of the Leeward Isles, including Anguilla and St Bart’s or St Kitt’s and Nevis, depending on conditions.

| 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 |

The principal town and capital of French St. Martin is Marigot, which is your embarkation port for this ocean passage. It’s an appealing spot with colourful houses and lively markets. If your travel plans allow you to arrive early, Marigot is also a great base for exploring St Martin’s many beautiful beaches (some of which are clothing-optional, if that’s your bag!). To get a good leg stretch you might want to try a hike up Pic Paradis, St Martin’s highest peak, for glorious views and potential monkey encounters!
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.

Being a round trip, this voyage allows the crew the ultimate flexibility with itinerary planning, and if there’s somewhere nearby that you’d love to visit, you should let the captain know. Favourite stopovers include the islands of Anguilla, Saint Barts, Saint Kitts and Nevis.
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!
Pointe-à-Pitre is nestled right in the heart of the aptly named ‘Grand Cul-de-Sac Marin’ on the South side of Guadeloupe. This makes it a haven for sailors as the water is largely very sheltered. The town boasts vibrant markets and a lively cafe culture. Enjoy an evening ashore with your new shipmates before a final night on board.

February in the Leeward Isles offers some proper winter sun, with only occasional passing showers. Daytime temperatures hover around 27°C, dropping to around 23°C at night. The sea is a glorious 26°C. Sailing winds are a fairly reliable 15 to 20 knots from the East or Northeast, and there can be some sizeable Atlantic swell, particularly between the islands. Expect some exciting sailing, but peaceful anchorages in the shelter of beautiful islands.
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.
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.
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.
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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