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Our Ship

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.

Since 2008, Tall Ship Windy is now 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: Our goal is to inspire those who may have never been sailing, as well as to intrigue those who are experienced sailors. An adventure on Tall Ship Windy 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 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), 4 pressurized “heads” (marine toilets), and two showers. On day cruises, Windy is certified for 150 persons on their three decks: the fore deck, midship deck and 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.

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 band onboard Tall Ship Windy sailing Chicago's Skyline 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.

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

Tall Ship Windy sailing in front of Chicago's Navy Pier and Lighthouse

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.

Amphitrite Digital Announces Employee Stock Grant Program

a group of people on a boat

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.

Tall Ship Windy Launches Discovery Sails for Youth Groups Hands-on Learning Experiences

View from the decks of Tall Ship Windy with full sails and the Chicago Skyline in the distance

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.”

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

Navy Pier and Chicago Skyline from Lake Michigan

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.

Amphitrite Digital Acquires Seas the Day Charters and Tall Ship Windy

Tall Ship Windy sailing on Lake Michigan with the City Skyline 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.