Voyage Filters

Beaches and Pirates’ lairs!

Berth Price

2 Berth Cabin En-Suite Price per person



Embark Disembark Vessel DurationVoyage No
Fri 27-01-2023, 19:00Antigua, Caribbean Fri 03-02-2023, 10:00Tortola, Caribbean Eye of the Wind 7 NightsEYE23/05

Starting from Falmouth Harbour in Antigua be sure you visit the museums and shipyard of the British navy in the time of the Napoleonic era. The short sailing distances ensure a good mix of sailing experience during the daytime and sufficient time for shore leave and swimming and exploring pirates lairs.

After Antigua it is hoped we will have be snorkelling in paradise off Pigeon Island. Then we will sail through the northern part of the Leeward Isles and over to the British Virgin Islands and the capital Road Town on Tortola, with it’s reef lined beaches and rainforests.

  • Voyage
  • Vessel


Relaxing in good company and visiting unique islands.

The short sailing distances ensure a good mix of sailing experience during the daytime and sufficient time for shore leave and swimming stops in the afternoon and evening.

Lots to explore ashore in both Antigua and Tortola, so worth extending your holiday if you can!


  • Just paradise at sea
  • En suite cabins & elegant interior
  • Good trade winds for exciting sailing
  • Exploring ashore
  • Star gazing and dark skies

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


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.

Once between the islands the sailing grounds are just about perfect for beginners and tall ship enthusiasts alike. The 80 miles to cross the open sea passage between St Martin and Virgin Gorda, so perfect for those wishing to disconnect from the digital world and live wi fi free for a couple of days. Look out for whales, frigate birds and turtles.


  • Island hopping to some of the most scenic beaches and coves of the Caribbean
  • Across the Caribbean Sea aboard a windjammer with a young and friendly crew
  • Attractive ports of embarkation and debarkation: Antigua and Tortola
  • Active sailing and manoeuvering on a 100-year-old tall ship … feel free to participate!
  • The grandeur of the ocean and its wildlife 
  • Caribbean flair ashore
  • Excellent onboard cuisine, delicious meals from morning to evening
snorkelling in the Caribbean
snorkelling in the Caribbean


Antigua – home of Classic Yacht Racing

The crew will welcome you on board at the cosy marina of Jolly Harbour on the sugarcane island of Antigua. Opposite the bay lies a pink and white sandy beach that stretches for miles, attracting adventurers, water sports enthusiasts, sun worshippers and beach walkers alike. The breathtaking sunset is the highlight of a romantic evening stroll, but you can see it from the deck of a square rigger. Embarkation takes place at 19:00 hours. Afterwards, there will be dinner together in the comfortable lounge, where you will quickly feel at home on the Eye of the Wind’s deck and soon get to know your fellow sailors.

The former British colony is not only famous for the annual Antigua Sailing Week, one of the most important regattas in the world, but also for its 365 dream beaches. After being discovered by Christopher Columbus, the settlement of the island was shaped by British colonial rule, which lasted around 350 years. The British Naval Fleet was based here and English harbour was one of the best hurricane holes to shelter in. Today instead of men o war careening their ships bottoms, or loading cannons, tourists enjoy restaurants in the old stone warehouse buildings and watch the pelicans diving into the harbour.

trade wind sailing on Eye of the Wind
trade wind sailing on Eye of the Wind

Island hopping, anchorages & time ashore

On a sailing voyage we never use the word itinerary, as skippers will always be aiming for the best sailing and shore landings for the forecast and most idyllic or sheltered anchors and ports. They are as keen as you to include some of the highlights described below, but you have to go with Mother Nature, not fight her. Where the ship goes ashore depends on the wind and weather conditions, and is decided at short notice by the captain, who will take your wishes into account whenever possible. This ensures that your sailing trip is a pleasant mix of adventure, relaxation, active participation and pure enjoyment.

Between Antigua and the Tortola are several islands, any of which we may stop by, including St Martin before our longest single passage over to the British Virgin Isles. Our tip: Saint Martin is considered the ‘culinary capital of the Caribbean’ – do not miss the local specialities made from the guava fruit.

caribbean landfall
caribbean landfall

“Virgins Ahead” cried the lookout

Many nautical miles later, the first of the roughly 60 British Virgin Islands will appear on the horizon. The Eye of the Wind will drop anchor off Virgin Gorda, the third-largest island of the archipelago. Here, the randomly arranged granite boulders of “The Baths” form small caves and pools, and invite you to explore and snorkel. In this natural lagoon you can enjoy the tranquility and a first-class swim, too. After a trip to the beach and a swim in the sea, you can round off the day with a glass of quality wine from the onboard bar while watching the sun go down.

Sail in the Caribbean with Classic Sailing
Road Town: Lush Greenery and turquoise seas


Average air temperatures are 26-28 degrees centigrade. Sea temperatures are a balmy 26-28 degrees.

If you are on the Atlantic ocean side of Caribean islands the seas can be boisterous and blue. In the lee of any big volcanic island or inside a protecting reef, the seas can be flat. The winds mixed with tropical sun are generally the reason why the Caribbean is a perfect sailing ground. Square riggers under full sail, generally create some shade somewhere on deck or in the rigging so you can always find a cool spot. There is air conditioning in the cabins.


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.


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.

Eye of the wind - big ships wheel
Eye of the wind – big ships wheel


Every customer sailing with us will need to fill in basic medical questions on their booking application. If you are not sure if your current level of fitness and agility are up to a voyage, then please ring the Classic Sailing Office on 01326 53 1234 and we can chat through your concerns and possibly find options that might suit you better.


  • Skipper & professional crew
  • Personal Safety Equipment
  • Sailing Instruction
  • All meals, snacks and refreshments
  • Port and landing fees
  • Linen and duvets
  • Third Party liability insurance


  • Travel to Joining Port
  • Travel from end port
  • Alcoholic Drinks but there is a bar on board
  • beach Towels
  • Waterproofs
  • travel insurance

Start & End Port

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.

Tortola, Caribbean


Kit List

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 


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. 


Eye of the Wind is an experienced operator with many happy customers. She sails in Northern Europa nad the Baltic in Summer (Northern Hemisphere) and across the Atlantice to the Caribbean for some winter sunshine sailing holidays.

Facebook Reviews currently 5 out of 5 stars 


Tortola to the Azores! What a great time. Thanks to Captain Pit and the crew. An awesome adventure with awesome people!" F Coutreau, New England


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 Schwartz

Dear Adam,

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


And such a beautiful ship.

Thank you beyond measure, Susan.

Eye of the Wind Faroes to Iceland Summer 2022

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. 

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