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Sunset Sails and Skyline Views: Exploring Chicago’s Waterfront with Tall Ship Windy

Michael Charles and his Band playing on board Tall Ship Windy's Monday Night Blues Sail at sunset

As the sun dips behind the iconic skyline of Chicago, a new chapter unfolds aboard Tall Ship Windy. Welcome to an enchanting journey of sunset sails and skyline views, where the shimmering waters of Lake Michigan provide the canvas for a breathtaking spectacle. Join us as we explore the beauty of Chicago’s waterfront from the unique vantage point of Tall Ship Windy.


Sailing Into the Golden Hour:

There’s something magical about the transition from day to night, and aboard Tall Ship Windy, this magic comes to life during the golden hour. As the sails catch the warm hues of the setting sun, the Chicago skyline transforms into a silhouette, creating a mesmerizing backdrop for an unforgettable sailing experience.


The Architectural Tapestry:

Chicago is renowned for its architectural prowess, and there’s no better way to appreciate it than from the deck of Tall Ship Windy. Sail past iconic landmarks like the Willis Tower, Navy Pier and the John Hancock Center, each building illuminated against the twilight sky. Our knowledgeable crew shares insights into the history and design of these architectural wonders.


Serenity on the Water:

Escape the hustle and bustle of the city as Tall Ship Windy glides gracefully on Lake Michigan. The gentle lapping of the waves and the soothing sound of the wind in the sails create a serene atmosphere, offering a moment of tranquility amidst the vibrant energy of Chicago.


Capturing the Perfect Moment:

Sunset sails with Tall Ship Windy are a photographer’s dream. Whether you’re capturing the play of colors in the sky, the reflection of city lights on the water or candid shots of friends and family enjoying the experience, every moment is a snapshot of pure beauty.


Elevate Your Experience:

Savor a selection of snacks and beverages as you toast to the day’s end and the night’s beginning. Our evening sails are not just about the sights but also about creating a sensory experience that lingers in memory.


Final Thoughts:

Sunset sails aboard Tall Ship Windy offer more than just a view; they provide an immersive journey into the essence of Chicago’s waterfront. It’s a chance to witness the city’s transformation under the twilight sky, a canvas painted with the vibrant hues of a Chicago sunset. Come aboard, and let Tall Ship Windy be your vessel into the enchanting world where the sun bids farewell to the Windy City.


April 1, 2024