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Sail Bermuda and The West Indies TOP026_11

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Sail Training Bermuda and The West Indies

Consider this your introduction to the West Indies.  This sail training adventure begins and ends in Bermuda and over the course of six months you’ll visit phenomenal places including the Windward and Leeward Isles, Bonaire, and Panama. With this much time at sea you’ll become a bonafide seafarer as you learn to navigate, haul on lines, take your turn on forward lookout, spend time in the galley, and so much more.  Sail the Caribbean and challenge yourself to grow and learn on this remarkable sea voyage.


  • A combination of short island hopping sails and long ocean passages
  • Small boat sailing to explore the many mangroves and bays around the islands
  • Swim and snorkel in tropical blue waters
  • Diving in Bonaire
  • Discover the UNESCO World Heritage Site of Cartagena
  • Explore Havana, Cuba
  • Be a hands-on part of the crew on this sail training adventure

The first weeks of this adventure will be spent in Bermuda going through orientation and sail training. Take the time to get to know your fellow shipmates – both guest crew and professional crew. The first sail is a deep-sea passage of 800+ nautical miles as you steer south through the Caribbean.  After that, you’ll spend a couple of months’ island hopping around Windward and Leeward Isles.

Next up are the British Virgin Islands and Bonaire where you’ll see the distinct Dutch influence on the island. The diving here is fantastic.  The next stop is Cartagena in Columbia, which is a designated UNESCO World Heritage Site.  There are three ports to stop at in Panama – the San Blas Islands, Portobelo, and Colon. Cuba is the last stop before beginning to head back to Bermuda.

This is a hands-on adventure and you’ll be trained on all aspects of sailing, maintenance, and even galley work. No experience is necessary – just a willingness to pitch in and a strong desire to learn.

What we love about this operator is that they have an insider’s view to sailing the Caribbean. You’ll get an authentic experience that most tourists won’t get. Over the years they’ve developed relationships and become part of the daily lives of the locals that live on these incredible islands.

Enquire today to learn more about this Bermuda & the Real West Indies sailing voyage.


Leg 1: St. George’s, Bermuda – January 4, 2017
British Virgin Islands – March 12, 2017

Leg 2: British Virgin Islands – March 12, 2017
Bonaire, Netherlands Antilles
Cartagena, Colombia
San Blas Islands, Panama
Portobelo, Panama
Colon, Panama
Havana, Cuba
St. George’s, Bermuda – May 31, 2017

Begin in Bermuda

This voyage starts at the Atlantic island of Bermuda, home of the Royal Naval Dockyard and historic port for British ships.  With air temperatures in the high teens in degrees Celsius, it makes a pleasant first port for those escaping the Northern Hemisphere winter.

The first days and weeks of the voyage will be spent in Bermuda on training and orientation, preparing the ship and crew for the voyage.  You will meet your shipmates and start to learn the ways of the ship.  Once the captain declares the ship and crew ready to set sail, you’ll get underway and steer south for the Caribbean.

After a deep sea passage of 800+ nautical miles, you will enjoy almost two months of island-hopping amongst the incredible Windward and Leeward Isles.  With steady trade winds blowing, we’ll have excellent conditions for sailing.

Conditions will also be excellent for sailing small boats.  The ship carries aboard a number of small boats, some used under power as the tender between ship and shore and as a rescue boat, some rigged for sailing so the crew can explore bays and mangroves.  Small boat training is valuable because it takes all of the skills required to sail the ship and makes the consequences more immediate.  Small boat expeditions are often also accompanied by a well-deserved swim call to cool off and occasionally a chance to snorkel in the tropical blue waters.

The ship has sailed the islands of the Eastern Caribbean many times.  Because we’re familiar with these islands, our crew have a very different experience than what’s available to a cruise ship or fly-in visitor.  The Caribbean we can introduce you to is authentic, not the made-for-tourists version.

There is the possibility that we may carry some cargo to the islands we’ll visiting, likely including some donated school books and supplies.  This is one of the ways we get to know people and cultures in the islands in ways that most visitors can’t access; we become part of the daily lives of those who live in these beautiful places.

Circle the Caribbean Sea

From the British Virgin Islands, we’ll set sail for Bonaire, which was part of the Netherlands Antilles until their dissolution in 2010, now it’s a special municipality of the Netherlands.  Dutch heritage is evident in the architecture, and the island is maybe best known for its incredible diving sites.  From British and Dutch colonial Caribbean ports, we’ll sail for some Spanish colonial Caribbean ports, the first of which is Cartagena in Colombia, with it’s old town named a UNESCO World Heritage Site.

Panama will follow, with visits to three ports.  They’re all so interesting and different, we couldn’t pick just one!  The San Blas Islands are inhabited by the indigenous Kuna people, makers of molas, intricate fabric designs created by layering.  Portobelo once was the greatest Spanish port in Central America, where silver was collected and loaded aboard ships for transporting back to Europe.  The forts to defend the treasure are now ruins, interesting to visit.  Colon is the gateway to the Panama Canal.  Although the ship won’t be transiting through the Canal on this voyage, it’s still fascinating to see the process and maybe to book passage on another vessel to make the day-long transit.

From there, we’ll make our way northeast to Cuba, calling at the capital of Havana.  We’re assured that people of all nationalities are welcome to visit Cuba, and who wouldn’t want to take in the unique culture in Havana and the surrounding area?

The last passage of this leg will bring us further north to the Bahamas, then to Bermuda, where this voyage will wrap up and Picton Castle will rendezvous with a fleet of tall ships for the next voyage.

The Ship

The ship is registered in the Cook Islands, in the South Pacific, and is owned and operated by the Windward Isles Sailing Ship Company, Ltd. Her mission is deep-ocean sail training and long-distance education. Also, she carries supplies and educational materials to far-flung islands in the South Pacific. Her North American homeport is Lunenburg, Nova Scotia.

The ship is a completely refitted barque that observes the rigorous standards of Germanischer Lloyds for steel-hulled Cape Horners. She is 179 feet overall, with riveted steel hull, clear oiled-pine decks, steel masts, and wooden and steel yards. She carries 12,450 square feet of canvas sail. The ship also has a powerful 690 hp Burmeister & Wain alpha diesel engine for occasions when sailing is not feasible. The galley is on deck, and its 1893 cook stove is similar to those used on commercial sailing ships 100 years ago.

There are berths for 40 sail trainees and 12 professional crew members. (Usually about half our trainees are men and half women. Their ages range from 18 to 60+, with the majority under 35.) Sleeping accommodations are bunkroom style, in two tiers of pilot bunks. Bunks have curtains for privacy and individual reading lights.

As a sail training ship trainees participate fully in the ship’s operation: handling sails, scrubbing the deck, taking a turn at the wheel, raising anchor, hauling on lines, helping in the galley, going aloft (optional), and keeping lookout. There are training classes in seamanship and navigation, plenty of opportunities to learn square-rig sailing and, on the world voyages, to explore exotic tropical ports and islands.

Become a Trainee

Everyone on board is a hands-on part of the crew.  Under the guidance of our professional crew, trainees literally learn the ropes.  As a trainee, you stand watches, take your turn at the helm and on forward lookout, handle lines and sails, help in the galley, work on ship’s maintenance, and do whatever it takes to keep the ship sailing.  Through the process of operating the ship, you develop seamanship skills as well as your ability to work with others, earning your way to each port.  It’s your dedication to the voyage and to learning the ways of the ship that make the voyage a success.

No experience is necessary to become a trainee, just good health and a strong desire to be a working crew member.  Men and women of all nationalities ages 18+ are welcome to apply.  All applicants are subject to a personal interview.

Dates & Rates

DatesLeg 1: St. George’s, Bermuda January 4, 2017 – British Virgin Islands March 12, 2017

Leg 2: British Virgin Islands March 12, 2017 – St. George’s, Bermuda May 31, 2017


  • Entire Voyage: 18,000 USD
  • Leg 1: 9,300 USD
  • Leg 2: 11,200 USD

Everything's Included

Whats included: your bunk and board, your share of the cost of running and maintaining the ship, port fees and entry fees for the countries we visit, plus, all instruction and training.

Just one week at an approved sailing school learning to sail a small boat will cost you $1,000. We teach you square-rig sailing, sail making, rigging, navigation and a host of other skills, those that are exclusively marine and those that easily transfer ashore.


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