Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"
Overview
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.
What's Included
- Restroom on board
- Snacks
- Alcoholic beverages Alcoholic Beverages
- Gratuities
Meeting Location
600 East Grand Avenue
Chicago, IL 60611, USA
Detailed check-in instructions, including the exact address, are provided with your booking confirmation.
This activity ends back at the meeting point.
What To Expect
Book Online
Safe & secure Easy breezy Hassle‑free
Chicago Skyline (pass by)
Additional Info
- Confirmation is instant and will be received at time of booking
- Service animals allowed
- Public transportation options are available nearby
- Travelers should have at least a moderate level of physical fitness
- This tour/activity will have a maximum of 150 travelers
Frequently Asked Questions (8)
Q: Will I get seasick on Sail on Tall Ship Windy, join us for our “Chicago Skyline Sail”?
Cancellation Policy
Still have questions?
We're here to help.
Activity code: C-5560540P2
Traveler Photos
Reviews
Average 4.83 out of 5 stars based on 30 traveler reviews collected by Key West Private Charters and partner sites such as Cool Destinations and TripAdvisor
Additional Info
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Frequently Asked Questions (8)
The answers provided below were previously given in response to questions from Key West Private Charters customers.
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If you have any doubts about becoming seasick on the water, we recommend taking a Dramamine® Motion Sickness Relief tablet the night before your trip. Some people recommend taking it the night before your cruise and then again that morning so you will not feel so drowsy.
Feb 2023- Restroom on board.
- Snacks.
- Alcoholic beverages. Alcoholic Beverages.
- Gratuities.
There is no minimum age for this tour, so bring your wee one along for an adventure. This tour requires at least one adult to accompany children..
Apr 2025If a date or time is not listed on the calendar, it’s sold out or unavailable for another reason. Support cannot assist further if a date or time is not on the calendar.
If you find a date and time that works for you, book it NOW because things always sell out at this time of year.
Apr 2025Accessibility information for the Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail" is as follows:
- Service animals allowed
- Public transportation options are available nearby
- Travelers should have at least a moderate level of physical fitness
Detailed check-in instructions – including meeting point address, Google map, and parking information – for Sail on Tall Ship Windy, join us for our “Chicago Skyline Sail” will be included in your confirmation email from Key West Private Charters. Please be sure to double and triple check your email address is correct at checkout so this important email makes its way to you!
Mar 2024Once your refund is processed, it usually shows on your card statement within 5–10 business days. The exact timing depends on your bank or card issuer.
Want it sooner? When you cancel, choose Receive a refund to my wallet instead. The credit is in your Wallet straight away and is applied automatically at checkout on your next booking when you’re signed in with the same email. You can see your balance any time in My Wallet.
If you paid part of your booking with Wallet credit, that part always goes back to your Wallet. Trip protection isn’t refundable.
Oct 2026What's Included
- Restroom on board
- Snacks
- Alcoholic beveragesAlcoholic Beverages
- Gratuities
Additional Info
- Confirmation is instant and will be received at time of booking
- Service animals allowed
- Public transportation options are available nearby
- Travelers should have at least a moderate level of physical fitness
- This tour/activity will have a maximum of 150 travelers
