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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.

Windy in the News

For the most recent Tall Ship Windy news, check out our updates below! 


Amphitrite Digital Reports First Half Revenue Growth of 40%

Monday Night Blues Aboard Tall Ship Windy at Sunset

This growth was driven by the company’s integration into Amphitrite Digital’s digitally enabled advertising, marketing and operating platforms. Windy of Chicago’s Tall Ship Windy came off Navy Pier at a record pace, achieving 42% growth for the first half of the year. New this year, guests can enjoy a concert sail, the Monday Night Blues, every Monday night. The Educational Sail, sailing three days a week, was moved from Fridays to Mondays and continued Saturdays and Sundays.

For the full story: HERE.

Five-Year Contract to Operate Tall Ship Windy on Chicago’s Navy Pie

Chicago skyline from Lake Michigan

Amphitrite Digital’s Windy of Chicago has been awarded a five-year contract to berth and operate Tall Ship Windy from Navy Pier. Tall Ship Windy is the official flagship of the City of Chicago which Amphitrite Digital, one of the nation’s leading tour activity operators, has operated since 2022 when Windy of Chicago was acquired by the company.

For the full story: HERE.

Amphitrite Digital Announces Employee Stock Grant Program

Captain at the helm of Tall Ship Windy sailing on Lake Michigan

The innovative Amphitrite Digital, which is bringing digital technology to the tour activity operator industry, is now offering a stock incentive program to its employees.

To kick off the program, the company awarded 1.52 million stock shares in Amphitrite Digital to 16 employees and contractors.

Read the full press release.

Windy Launches Free Discovery Sails for Non-Profit Youth Groups

Guests aboard Tall Ship Windy sailing on Lake Michigan

Amphitrite Digital, in partnership with Navy Pier, has launched the new fun and educational Discovery Sails program to provide hands-on, onboard experiences on the famous Tall Ship Windy. The free program will be open to local youth-oriented (7-17 years old) nonprofit organizations. “Hands-on training through Discovery Sails gives young people a rare chance to apply real-world physics, ecology, history and storytelling while taking an active part in sailing the ship,” said Amphitrite Digital President Hope Stawski. “History comes alive on the ship with an exciting educational adventure for curious minds of all ages. Best of all it’s fun.”

For the full story: HERE.

Tall Ship Windy Makes Way Down Chicago River to Summer Berth at Navy Pier


CHICAGO (WLS) — There was a majestic sight on the Chicago River Wednesday as the “Tall Ship Windy” made her way from winter storage to her summer mooring spot at Navy Pier.

For the full story: HERE.

Amphitrite Digital Acquires Seas the Day Charters and Tall Ship Windy

a large ship in a body of water with a city in the background

Leading tour activity company Amphitrite Digital is poised for continued expansion after its recent acquisitions of Seas the Day Charters in the United States Virgin Islands and Tall Ship Windy, the official ambassador for the City of Chicago. As the owner of predecessor operations of Seas the Day Charters USVI and Tall Ship Windy in Chicago, Amphitrite Digital is poised to leverage its digital operating foundation to expand its tour activity operator business in both the United States and the Caribbean,” said Scott Stawski, Amphitrite Digital’s chairman and chief revenue officer.

For the full story: HERE.