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Caribbean Ocean Sailing & British Virgin Islands – Paradise by Tall Ship

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2 Berth Ensuite Cabin Per person

Limited places


Embark Disembark Vessel DurationVoyage No
Fri 17-02-2023, 19:00Tortola, Caribbean Fri 24-02-2023, 10:00Tortola, Caribbean Eye of the Wind 7 NightsEYE23/08

A taste of ocean sailing in the Caribbean combined with island hopping in the British Virgin Isles. Eye of the Wind is a romantic looking tall ship with red sails and comfortable accommodation for only 12 guest crew. No experience is needed as the young, multi-national crew will show you the ropes. It’s up to you how much you get involved, but we think you will revel in setting more sail in the brisk trade winds.

  • Voyage
  • Vessel


  • Island hopping to some of the most beautiful beaches and coves of the British Virgin Isles
  • Enjoy some healthy exercise helping sail a windjammer with a young and friendly crew
  • Excellent onboard cuisine, delicious meals from morning to evening
  • Good balance of open ocean sailing and island exploring in the BVI
  • Warm water sea swimming and snorkelling.

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


Anyone wanting to learn to sail a square rigger in tropical sunshine with cooling breezes. Those looking for an outdoor life for a few days with a taste of ocean sailing exploring the British Virgin Isles. Between the islands the sailing grounds are just about perfect for beginners and tall ship enthusiasts alike. 



  • Island hopping to some of the most beautiful beaches and coves of the British Virgin Isles
  • Enjoy some  healthy exercise helping sail a windjammer with a young and friendly crew
  • Excellent onboard cuisine, delicious meals from morning to evening
  • Good balance of open ocean sailing and island exploring in the BVI
  • Warm water sea swimming and snorkelling.
snorkel over coral reefs in the caribbean
snorkel over coral reefs in the caribbean


Wander the British Virgin Isles: a near perfect sailing ground, tropical sunshine with cooling trade winds. Learning to be a tall ship sailor gives you a different perception of Caribbean Island life. The azure blue ocean is so bright you need sunglasses before breakfast and the underwater seas are full of colourful life. Richard Branson spotted the beauty of this island group many years ago and has a house on his own private Necker Island. If it is a good hideaway for the rich and famous, its good enough for us to come and play pirates.

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. The description below is based on what we think might be possible, based on past trips, or experience, but nothing is guaranteed on a sailing voyage.

star of white squall and other movies - eye of the wind runs caribbean sailing holidays
star of white squall and other movies – eye of the wind runs caribbean sailing holidays

Enjoy the smooth and steady rise and fall of the hull as this 100 year old vessels powers through the azure blue waves. It is nice to contemplate the vast ocean and how small human beings are, whilst listening to the soft creaking of the rigging and a cascade of tropical sea cascading down the lee hull. The perfect ingredients for a wonderfully relaxing holiday experience.

While this voyage will largely be island hopping, with anchoring overnight, there may be a chance for sailing in the inky dark of the tropics with only the stars and compass light to keep you on course. You will get to know the Eye of the Wind as a seaworthy and reliable ship that has proven itself in all weather conditions.

If you are feeling brave, or an experienced tall ship sailor you can climb the rigging with the crew as the ship is going along….or wait until you are in an idyllic anchorage with no roll. Or you can simply relax and enjoy the sights and sounds of a sailing ship on a sea journey.

climbing aloft on the eye of the wind
climbing aloft on the eye of the wind

Down Amongst the deadmen and pirates

After a night at anchor, we will cruise through the waters of the BVI. If yo look at the chart there are some amazing deep water passages between the islands but also lots of reefs, rocks and wrecks …..all with names that sound like they come from a pirate treasure map. Pelican Island, Dead Chest, Mosquito Island and Carrot Rock.

The flat water might give you a chance to go out in the zodiac whilst the ship is sailing and tack incredible photos of a square rigger in the Caribbean scenery.


The journey starts and ends on the main island of Tortola. It is well worth taking shore leave to see the port of Road Town, which exudes a special holiday feel with its combination of mild climate, beautiful landscape and Caribbean serenity. Why not make the most of your time by taking a walk through the botanical garden in the town centre? And on the Main Street of the British Virgin Islands’ capital, numerous colonial-style houses will tempt you to stroll through the shops and enjoy a drink or two in the bars and pubs. You will notice that a certain British etiquette is blended with the tranquility and cheerfulness of the “Caribbean way of life”. Here and there, the shores of the white sandy beaches are lined with mangrove trees and prickly cactuses. The constant sound of the Atlantic Ocean will dispel any thoughts of a cold, wet winter

Rum punch or cold beer. You have earned it
Rum punch or cold beer. You have earned it


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.


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

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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