About

Captain Bruce Randall is a USCG licensed 100-ton Master Captain who has lived in Chicago since 1993. He was born in New England and was raised primarily in the Quincy Ma, and sailed Boston Harbor area. 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. Bruce’s grandfather was a Boston Harbor Pilot, for 35 years. The Tall Ship “Highlander Sea”, which was named “Pilot” in its pre-restoration era was one of the vessels Grandfather served aboard. Bruce’s oldest brother Richard, served under their grand father as a Boston Harbor Pilot for some time, after serving in the USCG. Bruce’s brother, Captain Rodney Randall, served three tours aboard the Coast Guard Barquentine “Eagle” as a training officer, circumnavigating the world. Bruce acquired his early large boat experience, in this maritime “clan”, maintaining and sailing aboard his father’s “pride”, which was the 55-foot, 35 ton steel Ketch, “Reality”, and Captain Rod, is currently the Master Captain of Windy! (bio and picture coming soon!)

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 originally acquired Windy in 2008.

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 1980’s, and enthusiastically earned multiple certifications in keelboat, performance, navigation, bareboat cruising, and big boat racing. She has chartered, raced and cruised sailboats many times in the Caribbean, Greece and Italy, and locally here in Chicago, where she has lived and worked for 35 years. She is interested in the use of sailing experience and sail training for personal growth and discovery, and for relationship change. We’ll bet you’ll never guess WHO was one of her sailing teachers!

Karen has been a hands-on managing partner, working the boats and managing the business side, ever since the Randall’s teamed up and started sailing for a living. 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.

Windy provides the opportunity for guests to experience the thrill of sailing on an authentic tall ship on a safe and protected waterway. We invite you to embark on an unforgettable skyline sail filled with a variety of unique experiences. Enjoy a captivating architecture tour that unveils the hidden history of the Windy City’s skyline, thrilling pirate and maritime stories that transport you to a bygone era and enlightening educational sails that engage curious minds. As the sun paints the horizon in breathtaking hues, our sunset sails provide the perfect backdrop for romantic moments, fun nights out with friends and stunning photo opportunities. Join us for a Monday Night Blues sail, featuring live music to soothe your soul, or celebrate special occasions with our enchanting fireworks sails that light up the night sky. At our core, we are dedicated to creating memories, forging connections and crafting a unique, nautical experience like no other. Come aboard and let the adventures begin!

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.