About the Windy

The Tall Ship Windy, sailing from Navy Pier in Chicago, is a 148-foot, traditional four-masted gaff topsail schooner. She offers fireworks cruises, pirate cruises, and a variety of other public and private cruises in Chicago. She is built of modern materials, however, like old trading schooners and sail training ships, the WINDY has all the character and charm of the great Age of Sail.

Windy was built by Detyens Shipyard, Inc. of Charleston, SC. A custom design, she was conceived by Captain Robert Marthai “Captain Bob,” longtime sailor and traveler, who also became a maritime adventurer, maritime historian, designer, and shipbuilder. Windy was welcomed as the biggest and newest schooner to the Lake Michigan Fleet in July 1996. Windy reveals her designer’s love of the traditional sailing ship, yet integrates modern amenities and safety items such as pressurized plumbing, bow thrusters for docking, and a 300 hp Cummins diesel engine.

From the beginning, her mission was intended to bring Tall Ship sailing to the public, for enjoyment, personal and spiritual growth, and self-discovery. In the years since coming to Navy Pier, Windy saw many thousands of students, Girl Scout, Boy Scouts, youth groups, families, and other guests across her decks for educational cruises, daysailing, festivals, and religious, corporate, and private celebrations. Her skyline cruises became legendary and Windy was awarded the status of official flagship of the City of Chicago, by Mayor Richard M. Daley in 2006.


Windy Specifications


Since 2008, Tall Ship Windy has been the pride and joy of husband and wife owner/management team Captain Bruce Randall and Karen Randall. She continues the mission envisioned by her previous owners, gracing Chicago’s skyline with her majestic sails and noble and unmistakable profile. Windy provides an opportunity for people from all walks of life to experience an authentic tall ship and crew while sailing in a safe and protected waterway.

Windy’s mission: To offer an adventure on Tall Ship Windy that is ideal for families and groups wanting a fun/educational time, romantics of all ages, history buffs, those seeking creative and spiritual inspiration, or just friends out to have a wonderful sailing experience AND a truly unique view of our fair city of Chicago.

Windy’s Specifications: WINDY is the first certified four-masted traditional sailing vessel built in the U.S.A. since 1921. Constructed of steel, combined with wooden booms, gaffs, and deck ornamentation, she has three spacious decks with seating, a grand salon and galley (kitchen), four pressurized “heads” (marine toilets), and two showers. On day cruises, WINDY is certified for 150 persons on her three decks: the fore deck, midships deck, and the aft deck. On overnight cruises, Windy can accommodate up to 36 persons in 12 cabins including a 12 bunk “dorm” style accommodation. A favorite spot for guests is the aft great cabin (salon) with its large stern windows and varnished planked interiors, deep traditional gold, burgundy, and blue colors, all adding a bright warmth to the practical décor.


About Us


Captain Bruce Randall is a USCG licensed 100-ton Master Captain who has lived in Chicago since 1993. He is a member of a large maritime family, virtually all of the men in his extended family, and several of the women, have been professional sailors, sea captains, fishermen, and military mariners. His father was a one design sailing National Champion who taught him to sail almost from the time he could walk.

Since arriving in Chicago, in 1992, Bruce has been a sailing instructor, racing coach, and charter Captain on many vessels. He is also a accomplished sailboat racer. With the partnership of his wife Karen, the two began Lakeshore Sail Charters LLC (LSC) in 2003. They expanded into the Tall Ship world beginning in 2005, and nowadays you’ll meet Bruce on the Windy dock, supervising everyday operations, and if you are lucky, he may very well be Captain of the Ship that day!

Dr. Karen Randall also grew up in a sailing family, on Long Island, NY, with an older brother who was a one design National Champion in more than one class and also a winning solo sailor. She detoured away from the maritime world to pursue a career. A clinical psychologist by profession, she eventually returned to active leisure sailing and racing in the late 1980s, and enthusiastically earned multiple certifications in keelboat, performance, navigation, bareboat cruising, and big boat racing.  We’ll bet you’ll never guess WHO was one of her sailing teachers!

Tall Ship Windy is Bruce and Karen’s second schooner as a husband and wife owner management team. Now they have completed the circle of sharing the beauty of sail with individuals, groups, and students from all walks of life and with an ample range of number of guests. Captain Bruce says, “It has been the opportunity of a lifetime to serve our great city, showcase its beauty and its resources, and to advance ecological mindedness and conservation in the public awareness.” Tall Ship Windy is longtime member of Tall Ship America, dedicated to the advancement of maritime knowledge and traditional sailing skills aboard Tall Ships.