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About Us

Our Story

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. Learn about our parent company, Amphitrite Digital and our founders Captain Bruce and Dr. Karen below.

Amphitrite Digital

Amphitrite Digital’s Mission is to Bring Digital Technology to the Tour Activity Operator Industry. Amphitrite companies serve more than 50,000 guests annually and are the leading providers in each of their markets. Tall Ship Windy became part of the Amphitrite Digital family of companies in January of 2022. Amphitrite Digital companies also include Seas the Day Charters in the U.S. Virgin Islands; the leading boat charter company in the Caribbean.  Amphitrite Digital is proud to continue the maritime tradition established by Tall Ship Windy’s founders.

Captain Bruce Randall

Bruce 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

Karen 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 and management team. Now they have completed the circle of sharing the beauty of sailing with individuals, groups, and students from all walks of life and with an ample 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 a longtime member of Tall Ship America, dedicated to the advancement of maritime knowledge and traditional sailing skills aboard tall ships.