Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"

Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This is a relaxing sailing Adventure, that you will enjoy, on Lake Michigan, while enjoying the views, an

Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This is a relaxing sailing Adventure, that you will enjoy, on Lake Michigan, while enjoying the views, and the fresh air! Fun for all ages! You can join our friendly crew, to help raise one of the many sails on Windy, or just relax, and let others do the work! Windy has a full bar, and a gift shop, to help you enjoy the sail.

From: $0.00

Location: Chicago

What's Included

Community Discussion

Q&A

Q: Is there an age limit for the Chicago Skyline Sail on Tall Ship Windy?

A: No, there isn't a specific age limit! It’s fun for all ages, so feel free to bring the kids along. Just keep in mind that young ones should be supervised, especially near the edge of the deck. They’ll love the views of the skyline!

Q: What should I wear for the Chicago skyline sail? Is it chilly on the water?

A: Layering is key! It can get breezy on Lake Michigan, especially in the evening. I recommend wearing a light jacket or sweater, and don’t forget comfortable shoes. If you plan to sit outside, bring a blanket just in case it gets chilly.

Q: Can you reschedule if the weather is bad?

A: Yes, they allow rescheduling due to weather! You can usually move your booking at no extra charge. Just be sure to check their policy in advance. They want everyone to have a great experience!

Discussions

Just booked a Chicago Skyline Sail! Any tips?

I just bought tickets for the Tall Ship Windy skyline sail for next month! I’m so excited but a little nervous about the weather. How’s the experience usually? Is it crowded? I want to make sure it’s a great gift for my parents!

Anyone done the Chicago Skyline Sail recently?

I’m thinking about this sail as a birthday gift for my sister. I heard it’s relaxing and I love that it’s fun for all ages. What’s the best time of year to go? Any must-see sights?