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Sailing through Time and Waves: Aboard Tall Ship Windy in Chicago

View of the Chicago skyline at twilight from the decks of Tall Ship Windy

Chicago, a city known for its magnificent skyline, rich history and stunning lakefront, offers a unique experience that combines all of these elements in a truly memorable way. Aboard Tall Ship Windy, visitors will embark on a voyage that takes them back in time while enjoying the modern marvel that is Chicago’s skyline. In this blog, we’ll explore the captivating world of boat cruises on Tall Ship Windy in the Windy City.


A Nautical Journey through History

Tall Ship Windy is not just any boat; it’s a meticulously crafted, historically accurate replica of a 19th-century sailing vessel known as a topsail schooner. Its tall masts, billowing sails and intricate rigging transport guests to an era when these majestic ships ruled the waters.


As you step aboard, you can’t help but feel like you’ve stepped back in time. The crew welcomes you warmly and shares stories of the ship’s history and its role in Chicago’s maritime past. It’s a unique blend of education and entertainment that sets the stage for a remarkable adventure.


Sailing on Lake Michigan

Tall Ship Windy cruises along the shoreline of Lake Michigan, one of the Great Lakes and a defining feature of Chicago’s waterfront. Lake Michigan is so vast that it feels like an inland sea and from the deck of Windy, you’ll have the opportunity to appreciate its grandeur fully.


As you set sail, you’ll witness the city skyline to one side of the ship and to the other, an unobstructed view of the vast expanse of the water. On a clear day, you can see for miles and the contrast between the endless horizon of the lake and the towering skyscrapers of Chicago is truly breathtaking.


A Lesson in Sailing

For those who are curious about the art of sailing, the crew of Tall Ship Windy is more than happy to share their knowledge. They explain the basics of operating a topsail schooner, demonstrating how to raise and lower the sails and even allow guests to lend a hand. It’s a hands-on experience that adds an extra layer of enjoyment to the cruise.


Spectacular Skyline Views

As the ship glides through the water, you’ll have ample time to take in the iconic Chicago skyline from a unique vantage point. Whether it’s the towering spires of the Willis Tower (formerly Sears Tower), the sleek lines of the John Hancock Center, or the historic charm of Navy Pier, each landmark tells a story about Chicago’s architectural and cultural history.


The play of sunlight on glass and steel, the shimmering reflections on the water, and the ever-changing colors of the sky create a visual spectacle that’s both serene and exhilarating. It’s a photographer’s dream and even if you’re not a photographer, you’ll find it impossible not to snap a few pictures to capture the moment.


A Memorable Experience

Tall Ship Windy offers various cruise options, including daytime and evening sails, as well as themed cruises for special occasions. Whether you’re looking for a romantic evening under the stars, a family adventure, or a unique way to celebrate a milestone, there’s a Windy cruise to suit your needs. Click here to explore your options


In conclusion, a boat cruise aboard Tall Ship Windy in Chicago is an enchanting and educational experience that combines history, adventure and stunning views. It allows you to connect with the city’s maritime heritage, appreciate its awe-inspiring skyline and bask in the natural beauty of Lake Michigan. It’s an adventure that will leave you with lasting memories and a deeper appreciation for the Windy City’s unique blend of past and present. So, when you find yourself in Chicago, don’t miss the opportunity to set sail on Tall Ship Windy and let the wind carry you on a journey through time and waves.



November 1, 2023