Watching Fireworks from Navy Pier has become a Chicago tradition. And, there is no better seat in the house to watch the show than sailing aboard 148′ Tall Ship Windy – the Official Flagship of the City of Chicago! Order a cold drink from our bar and enjoy a thrilling fireworks performance as you sail along the stunning and iconic Chicago skyline during this special event sail.
Chicago Skyline Sail Aboard 148' Tall Ship Windy
Experience breathtaking views of Chicago from the waters of Lake Michigan! Leave the hustle and bustle behind and explore Chicago’s gorgeous shores and skyline with a leisurely trip around Lake Michigan.
- Standard Boarding
- Adult Ages 13+
- Child Ages 0-12
- VIP Captains Boarding
- Adult Ages 13+
- Child Ages 0-12
There’s no better place to view Chicago or Lake Michigan than aboard 148′ S/V Windy; the Official Tall Ship Ambassador for the City of Chicago. Don’t miss these scenic and educational cruises from Chicago’s famous traditional tall ship! Select from Pirates and Maritime Stories at 1pm, Architectural and Skyline Tour at 3pm, Sunset and Skyline at 5pm and Late Summer Twilight at 7pm.
Experience The Beautiful Chicago Lakefront With Three Sailing Options
Tall Ship Windy offers three exciting ways to enjoy the Chicago lakefront and skyline. Learn more about our Skyline sails and book today!
1pm. Pirates and Maritime Stories
Join us on our main deck for “True Stories of Piracy” on the Great Lakes and the Caribbean! From epic battles to trickery and treasure, experience the incredible tales of real pirate adventure that happened right here on these magnificent inland seas. This Chicago sail is both educational and entertaining!
On this unforgettable sail, you will also enjoy awe-inspiring views of the world-famous skyline of the Windy City while sailing the gentle waters of Lake Michigan. There’s something for everyone on this fun tour.
3pm. Architecture and Skyline Sail
Experience breathtaking views of Chicago from the water! Leave the hustle and bustle behind and explore Chicago’s gorgeous shores with a leisurely trip around Lake Michigan. Take in the world-famous skyline, enjoy spectacular views and discover the Windy City from the water. This 3pm tour features the history of Chicago and its world-famous architecture. To learn about the people, plans and persistence that shaped Chicago’s most famous sights join us on the main deck and enjoy the lively and educational narration.
5pm. Sunset and Skyline Sail
Head out on our traditional tall ship and explore the majesty of Lake Michigan while Windy sails across our beautiful lakefront Chicago skyline. From the world-famous Tall Ship Windy, experience the phenomenal sun setting across the Chicago Skyline. A perfect Sunset Skyline Sail for individuals, family and friends.
7pm. Late Summer Twilight Sail
Enjoy the beautiful colors splashed across the post-sunset sky as you enjoy an evening sail on Lake Michigan aboard Tall Ship Windy. As you sail on Lake Michigan, enjoy spectacular views and take in the world-famous Chicago skyline as day transitions to night.
- VIP boarding
- Trip insurance
You can purchase these optional items when you book:
- Trip Insurance: $8.00 per person—gives you the ability to cancel your reservation if needed and receive a full refund. This applies up to 8 hours before your scheduled sail time or if Tall Ship Windy cancels your sail due to weather.
- No-shows will be charged the full price. Guests must arrive at least 15 minutes before the scheduled departure time or risk forfeiture.
- The captain reserves the right to postpone the sail for up to 30 minutes; if the sail is cancelled, tickets may be exchanged for another time.
- No refunds and no exchanges are available without the purchase of additional Trip Insurance. The Windy sails rain or shine. In the unlikely event that your tour is cancelled due to rain, we will provide you an exchange or refund.