Caribbean Expedition Sailing from BVI to Bermuda
- Vessel: Eye of the Wind
- Where: BVI/Bermuda
- Duration: 11 days
- Embark: Road Town, Tortola - 25 February 2023, 19:00
- Disembark: St George's, Bermuda - 7 March 2023, 10:00
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Immerse yourself into sailing a traditional tall ship as you sail from the British Virgin Islands to Bermuda.
Set sails from the island of Tortola in the British Virgin Islands (BVI) to as you tuck some sea miles under your belt and sail with Eye of the Wind to the island of Bermuda.
This voyage is perfect for those adventurers looking to spend more time at sea with open water sailing on a classic tall ship. No experience is needed as the professional and friendly crew are on hand to show you the ropes.
- Fully crewed tall ship
- Sea mile builder
- Great for adventurers
- Private ensuite cabins
- Longer passage at sea
- Sail area & highlights
- Gallery
- Life on board
- Sample menu
- Travel planning
- The boat
- FAQs
- What's included
- Boat schedule
YOUR SAILING AREA
Expedition Sailing, Caribbean
Through seemingly endless seas, the trade wind pushes Eye of the Wind through the azure waters of the ocean from Tortola to Bermuda. The soft, steady up and down of the ship’s hull in the waves, the expanse of the sea, and the permanent gentle creaking of the rigging are the perfect ingredients for a relaxing and at the same time, adventurous holiday experience. It is a 1000 mile journey to Bermuda and will take us 11 days to make the passage.
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Take the helm, become a member of the deck crew, and settle into the watch system, as life at sea takes over. You will learn every aspect of sailing a classic tall ship on this ocean sailing voyage. As you leave the islands of the Caribbean behind, fully immerse yourself into life on the ocean, with golden horizons and deep blue waters.
Bermuda is only 21 square miles but comprises of 181 named islands sitting way out in the Atlantic, hundreds of miles from the USA and several thousand from the UK. An elegant destination of perfect sandy beaches palms and colonial old world charm Bermuda is decidedly British compared with the Bahamas. The beautiful colonial town of St George’s is sure to entice you, with its waterside bars and restaurants.
All voyages for Eye of the Wind
Eye of the Wind
Guest berths: 16 Rig: Brig
With incredible amounts of character, Eye of the Wind has all the modern amenities and an authentic interior, with a teak maritime décor. Oozing with maritime history, the opportunity to sail on Eye of the Wind is one in a lifetime. This beautiful ship is as eye-catching as they get and she has even featured in several movies, including White Squall, due to her breath-taking appearance as a 1911 brig.
This windjammer offers luxurious holidays on board, cruising some of the most stunning locations in the world.
Although the ship has a large, capable engine, traditional sailing is naturally the preferred mode of travel so there is plenty to get stuck into on deck. The crew are extremely experienced and ready to teach you the workings of a classic tall ship, so no prior knowledge is necessary. Join the crew at any number of the large maritime festivals they appear at, cruise the European coast, or relish some winter sun and climb aboard for their voyages in the Caribbean – including a transatlantic crossing back from the Caribbean to Portugal.
Thanks to the 6 luxurious cabins, all with ensuite bathrooms, Eye of the Wind can sleep a total of 12 guests ensuring ocean passages can be travelled in true comfort. A large dining area, library and sun deck offer a multitude of different spaces to unwind and to get to know your fellow guests and crew.
Deck plan

Life on board
Sailing with Eye of the Wind is an experience that will sit close to your heart as you learn the ways of traditional, authentic sailing and explore breath-taking destinations. Sailing with such a historic vessel is a wonderful privilege and the pride that the crew have for working with such a vessel, is truly inspiring.
Getting involved
With her impressive red sails and traditional square rig, guests are actively encouraged to get involved with all aspects of sailing Eye of the Wind. The crew are friendly, professional multi nationals, who are well-versed in showing guests the ropes, so you don’t need any experience to climb aboard her voyages. There is no expectation to get involved with sailing this magnificent vessel but guests are encouraged to take part in sail hoisting, navigation and taking the helm. A good sense of humour and a sense of adventure is a must and if guests just want to sit back and relax with the harmony of the sails, that’s fine too!
A Typical Day
Most of Eye of the Wind’s voyages are designed to sail by day to explore new destinations and spend the nights in harbour or on a sheltered anchorage. The day to day itinerary is not set in stone so the Captain can make best use of the weather and winds. Once you board, a rough plan for the week will be explained and some basic sail functionings explained too!Â
Sailing on the high seas is hungry work, and your appetite will be easily satiated by our excellent on-board kitchen. From morning till evening, the chef will surprise you with varied recipes from his gourmet cookbook. Depending on the sailing season, local food and ingredients often end up in the cooking pot or on the plate. From a continental breakfast to lunch served either at anchor or underway. Dinner and drinks are normally served at around 7pm as you relax with your fellow guests and crew.Â
The day is a good balance of authentic traditional sailing with time to explore secluded bays, different cultures, cuisines and history ashore. Down-time is as encouraged as hands-on sailing, with air-conditioned bunks, comfortable lounges and a sun-drenched deck, ensuring that there are plenty of spaces to relax on board.
Sleeping and Relaxation
Thanks to the 6 luxurious cabins, all with ensuite bathrooms, Eye of the Wind can sleep a total of 16 guests ensuring voyages can be travelled in true comfort. A large dining area sits with the galley at deck level offering 360 degree views of the horizon. A library and cosy saloon sit below decks – the perfect place for relaxation and sharing sea-faring tales after a day at sea.
Above decks there’s cushioned bench seating, sun decks and a multitude of different spaces to unwind. Out at sea, you have time for yourself and time to get to know the ship as a place of rest, where you can leave the hustle and bustle of everyday life behind you. Stress has no place on the ocean, and you will find yourself unwinding in harmony with the wind and the sea on board Eye of the Wind.
What’s included
- All inclusive (breakfast, lunch, dinner, snacks and soft/hot drinks)
- All bedding (pillow, sheets & duvet) and a wash towel
- Full crew plus tuition
- Marina and fuel fees
- All tender trips to and fro the boat
- Lifejacket
What’s not included
- Alcohol
- Swim towel
- Waterproofs
- Any flights
- Transit hotels
- Travel to and from the boat on the day of joining/leaving
- Travel insurance
- Sailing Insurance (Please read our Sailing Insurance page for more information)
- Crew tips
- Personal expenses
Travel insurance notes
As this is an active adventure holiday, we advise that everyone has the appropriate personal accident travel insurance whilst onboard in addition to standard travel insurance which would cover you in the time between making your booking and departing for your adventure. These policies can sometimes be combined so please check with your travel insurance provider.
Please read more information on our Insurance guidelines page.
FAQ
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Are all meals included?
Yes. Breakfast, Lunch, Dinner, Hot and Soft drinks are included in your ticket price. Alcohol can be purchased as extra onboard
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Can you cater for dietary needs?
Yes, please let us know when making your booking.
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What language is spoken on board?
English and German
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Do I need to tip the crew?
Tips are not mandatory but are welcomed by the crew!
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What are the sleeping arrangements?
There are 6 cabins and a total of 16 guest bunks.
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How many bathrooms does she have?
Each cabin has its own ensuite.
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Is there an age limit?
No! Please double check for under 8's.
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Is there WIFI?
No, but you should easily reach 3/4G from the shore, just make sure your phone is set up for international roaming. There may be some locations that will not get good signal.
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Can I charge my phone/camera?
Yes, 12V sockets are available
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Are there life jackets provided?
Yes.
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Are Waterproofs provided?
No, please bring your own.
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Do I need sailing experience?
Not at all. We give everyone who joins us on board the choice to do as much or as little as they like.
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Will I be seasick?
Everyone reacts differently but if you are unsure, we recommend taking tablets up to 24 hours travelling.
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Is there air conditioning?
Yes, Eye of the Wind has air con in each cabin.
Gallery
imageimageimageimageimageimageimageimageimageimageimageimageimageimageimageimageimageimageimageimageimageimageTravel Planning
From: Road Town, Tortola
To: St George's, Bermuda
To see where the ports are, along with your likely sailing area, please view the sail area & highlights.