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About Us

Our Story

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.

Windy of Chicago and Tall Ship Windy joined the Amphitrite Digital family of companies in 2022. Windy of Chicago’s founders Captain Bruce and Dr. Karen Randall expanded into the Tall Ship world beginning in 2005, with Tall Ship Windy as the second schooner operated by the husband and wife owner and management team. Captain Bruce says, “It has been the opportunity of a lifetime to serve our great city, showcase its beauty and its resources and advance ecological mindedness and conservation in the public awareness.”

Amphitrite Digital

Tall Ship Windy is a proud member of the Amphitrite Digital family of companies. Amphitrite Digital companies and their dedicated employees and partners host 90,000 guests annually and provide the opportunity to enjoy ‘A Day, a Week and a Lifetime’ of experiences.

With a foundation rooted in digital technology and innovation, Amphitrite Digital uses advanced digital technology platforms to market, manage and operate in-destination tours, activities and events in the U.S. and the Caribbean. With several operating entities in addition to Tall Ship Windy in Chicago, Illinois which include Seas the Day Charters USVI and Magens Hideaway in the Caribbean and Paradise Adventures Catamarans and Watersports in Panama City Beach, Florida; Amphitrite Digital is one of the largest maritime tour activity operators in the markets they serve. Amphitrite Digital companies are consistently ranked as leading tour activity operators.

Sail in Florida and the Virgin Islands!

Paradise Adventures Catamarans and Watersports

Panama City Beach, Florida

Enjoy top-rated boating adventures on the Florida Gulf Coast at Paradise Adventures Catamarans and Watersports!

  • Experience inflatable fun on a Privateer Adventure Tour
  • Snorkel and explore Shell Island
  • Look for dolphins on a Sightseeing Tour or enjoy a Breathtaking Sunset Sail
  • Book a private charter on a catamaran, sailboat, powerboat or pontoon boat

Learn more about Paradise Adventures

Seas the Day Charters USVI

US and British Virgin Islands

Enjoy a full or a half-day adventure with Seas the Day Charters USVI!

  • Luxury sailing excursions & fast powerboat adventures
  • Private & semi-private charters available
  • Snorkel with beautiful fish, coral and sea turtles and explore white sandy beaches
  • Explore the US Virgin Islands or the British Virgin Islands

Learn more about Seas the Day Charters USVI