Explore Chicago’s Skyline with a 75-Minute Sail - Departing from Navy Pier with Tall Ship Windy (Up to 25% Off)
Amenities
Good for Groups
Parking
Good for Kids
Step aboard a vessel where history meets horizon. With towering masts and canvas sails overhead, Tall Ship Windy takes you on a ride that’s equal parts adventure and serenity. Conveniently located at Navy Pier, Tall Ship Windy is the first official Tall Ship Ambassador of the City of Chicago.
Chicago pulses with energy — but just beyond its bustling streets lies a world of calm, rhythm, and wonder. That world begins aboard Tall Ship Windy, where wind, water, and wooden decks converge to create an unforgettable adventure. Whether you're sailing under the golden glow of a setting sun, watching fireworks burst above the cityscape, or simply enjoying the cool breeze with a drink in hand, this is more than a sightseeing trip. It’s a chance to reconnect — with the city, with nature, and with yourself.
What We Offer
- 75-Minute Skyline Sail for Adults (age 13+) and Children (age 1-12) - Valid for Trips May 16 - September 28, 2025
This limited-time offer invites both adults and children to embark on a 75-minute sailing journey aboard the iconic Tall Ship Windy, cruising along the stunning shoreline of Lake Michigan. Whether you're traveling in spring, summer, or early fall, this offer spans three full sailing periods from May to September, making it easy to plan the perfect escape.
Your ticket includes access to the full 75-minute cruise, onboard amenities like snacks and drinks for purchase, and the chance to experience one of the most scenic and relaxing excursions in the city.
Quick Details
- Ages: All Ages
- Duration: 1 Hour and 15 Minutes
- Schedule: Sails Daily 1pm, 3pm, 5pm, 7pm - May 16 - September 28, 2025
- Location: Navy Pier (Directions)
- Booking: Must reserve your trip online after purchase
- Departure: Boarding starts 30 minutes before the scheduled start time. Please allow plenty of time for parking.
Why You Should Grab The Offer
When most people picture Chicago, they see it from the ground. But those who know where to look — or rather, where to sail — understand the true magic begins on Lake Michigan. Tall Ship Windy offers more than just a sail; it’s a rare chance to escape the city’s noise and experience its legendary skyline in peaceful motion. From daytime skyline cruises and thrilling fireworks sails to Monday night concert journeys and VIP upgrades for an elevated touch, every voyage is steeped in history, beauty, and charm. With onboard snacks, refreshing drinks, and a breeze that whispers stories of the past, this floating experience is unlike anything else in the city. Whether you're visiting for the first time or rediscovering your hometown, there’s no better way to fall in love with Chicago all over again.
Need To Know Info
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Additional Info
- Booking: Online reservation required. May purchase multiple to accommodate your group size.
- Restrictions: Valid only for option purchased. Taxes not included and collected at time of booking. Trips sail rain or shine. It is up to the captain to decide whether to sail, postpone or cancel.
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Refunds & Cancellations
- All sales final.
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Legal Disclosures
- Expiration varies. Amount paid never expires.
- Merchant is solely responsible to purchasers for the care and quality of the advertised goods and services.
- Learn about Strike-Through Pricing and Savings