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Hoist the Sails on a Historic Ship

There are few sights as eye-catching as seeing the Roseway making her way across the turquoise waters of the Caribbean into the harbor. The Roseway is a beautifully restored 137′ schooner with massive russet colored sails that is registered as a U.S. National Historic Landmark in both Boston and St. Croix. This regal vessel is owned and operated by the World Ocean School, which operates in South Carolina, Georgia and the Caribbean from November to May, providing a platform for curriculum integrated educational programs for students of all ages.

Roseway was originally designed as a fishing yacht by John James and built in 1925 in his family’s shipyard in Essex, Massachusetts.  The Roseway is one of only six surviving Grand Banks schooners, and the only schooner specifically designed to beat the Nova Scotians in the international fishing vessel races of the 1920s and 1930s. Following her use for racing and fishing, during World War I in 1942, Roseway was fitted with a .50-caliber machine gun and used by the Boston Pilots Association to guide ships through the minefields and anti-submarine netting protecting the harbor.  After her retirement from naval use in 1973, Roseway was transformed into a Windjammer and started cruising in 1975.  Roseway then starred in the television remake of Rudyard Kipling’s ‘Captains Courageous’ in 1977.  Finally, in September 2002, the bank that owned the Roseway honored a request by the World Ocean School and donated Roseway to be used for the school.  Since then, St. Croix has become the winter home port for Roseway and she summers in the Northeast, primarily in Boston, providing educational programs and day sails for the public.

I highly recommend that you book a day sail on the Roseway while here on St. Croix and allow yourself the amazing experience of hoisting the sails on this historic tall-ship!  Stepping onto the ship is like stepping back in time.  As you stand on the wooden deck make sure to look up and marvel at the enormity of the two masts.  Also, make sure to tour the entire deck and take in the details of this impressive schooner such as the intricate rigging, the wooden helm, the huge anchor stowed on the port side of the bow, the beautiful brass ships bell, and the array of knots used for both utility and stowage of the lines.

Once underway, you will be given the opportunity to be part of the action as the crew recruits passengers to grab a line and help to hoist the 5,600 square feet of sails.  After lining up along the side of the ship, you firmly plant your feet and grasp the huge line in your hand, then the staff crew leads as you rhythmically hoist the sail by pulling the line hand-over-hand in unison (or heave, ho as the sailors say).  The weight of the sails is unbelievable, and it feels very rewarding to look up at the billowing sails and know that you were part of the ‘crew’ that raised them up those massive masts.

Roseway Sunset Sails

Once the sails are up, enjoy the smooth sailing Roseway offers here around St. Croix as you relax on deck and enjoy the view, or explore the vessel and take in the splendor of this sailing landmark.  The Roseway is docked on St. Croix from November through April, and offers sunset sails to the public Sunday – Friday, as well as public day sails and private charters. To book your sail, or to confirm the current schedule and cost, please call (340) 626-7877 or visit Come and be part of history today by hoisting the sails and experiencing the National Historic Landmark that is the Roseway.

Editor’s Note: The schooner Roseway is currently undergoing a major refit. The Denis Sullivan, a replica Great Lakes sailing schooner, is coming in her place until she is in shipshape and returns back to making her seasonal voyages to St. Croix. 

– Jennie Ogden, Editor



Denis Sullivan Sunset Sails

Come aboard this replica of a Great Lakes schooner, Denis Sullivan, to enjoy a sunset cruise. Previously the historic schooner Roseway  has offered sunset sails in the winter and spring from St. Croix, but while Roseway is being refitted...

Gallows Bay, East End
(617) 816-9247


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