Chicago Skyline Sunset Sail Aboard a Tall Ship
4.8
28 Ratings
Chicago
Duration: 1 hour, 15 minutes
Cancellation: 1 day learn more
What's Included
  • On-board WiFi
  • Goods and Services Tax (GST)
  • anding and/or facility fees
  • On-board restrooms
What's Not Included
  • Alcoholic Beverages
  • Snacks
  • Gratuities
Additional Information

The famous Tall Ship Windy sunset sail is truly famous. Used in many world-renown photos, backdrops for special events, weddings, or just an evening out, the sunset sail aboard one of the only four-mast Schooners still in operation will not disappoint. You will enjoy a sail on Lake Michigan and at just the right moment, S/V Windy will gently turn toward the Chicago skyline for a view of our spectacular sunset. Sit back and relax, enjoy some soothing music, and gently complete your day with this dramatic sunset.
** Please note, tickets purchased for sunset sails on Monday evenings will be upgraded from our traditional 75 minute sail to our Monday Night Blues Summer Concert Series, which departs the dock at 7pm and returns at 9pm. Enjoy live Blues music and 45 extra minutes aboard beautiful Tall Ship Windy!

Location
600 E Grand Ave
East Grand Avenue
Tall Ship Windy is located at Navy Pier immediately across from Billy Goats Tavern and Shakespeare Theatre.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
4.8
(28 Ratings)
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Olga_p
Oct 1, 2023
A boat ride definitely worth repeating. - The crew was amazing. They were very entertaining and made the experience truly enjoyable. Having a bar on board and bartender with a great sense of humor is definitely a plus!!
Review provided by Viator
Meander04733761196
Sep 21, 2023
Fun Family Activity - The evening cruise was the perfect family activity for our weekend trip to Chicago. We set sail on time and enjoyed a smooth ride as we enjoyed sunset views of the city. The crews’ upbeat personalities, Caribbean drinks, and fun music added to a relaxing and fun vibe!! I highly recommend!!
Review provided by Tripadvisor
Rogerhf9326sw
Sep 21, 2023
Flawless Perfection - Honestly, a perfect experience. Exactly on-time departure and arrival. Perfect boat - size and look. The Captain and crew were friendly and knowledgable. My son raised the sail. Hard. Fun. An experience. The frozen drinks and cold beers were excellent. The views? Wow. A great soundtrack plays during the excursion at perfect volume level. A great time for all ages of Pirates. I guess I liked it :) Just do it. Thank me later.
Review provided by Tripadvisor
Csseng1
Sep 10, 2023
Blown away! - We’ve been to Chicago many times but have never experienced the city from this perspective. We were blown away at how beautiful the skyline is at sunset.
Review provided by Viator
Delilah_t
Sep 5, 2023
Excellent Evening - The crew, boat and evening were perfect. The crew was engaging and lively which added to the wonderful experience.
Review provided by Viator
Bonnie_f
Sep 5, 2023
Great Experience - Beautiful views, great music, peaceful boat ride! Definitely would go again! My family really enjoyed it!
Review provided by Viator
Barbara_s
Aug 22, 2023
Stunning sunset sail with 4 generations of our family! - We had a fabulous time with 4 generations of our family on the main deck for a Monday sunset sail! It was so beautiful and the live musician added so much to the experience! The crew were extremely helpful in providing extra care for my nearly 90 year old granny and my mom who is a bit frail in between her cancer surgery and start of chemo.
Review provided by Viator
Natalierq2196wi
Aug 10, 2023
Sailing in clouds - I come from a landlocked state so the opportunity to be on the water and enjoy sailing was wonderful. The crew was entertaining and friendly, and answered questions with humour. They created a safe place for all on board, and got people involved in the advaenture. Even though it was a chilly and cloudy evening it was still a brilliant evening for a sail. I enjoyed it so much I even considered taking another sail on a different day although it didn't work out. #tallshipwindy
Review provided by Tripadvisor
Lynn_o
Sep 9, 2023
Fun evening overlooking Chi town - The girl that did the commentary was pretty funny. And good. Was nice that we actually sailed. Even though it was for a short time was still nice!!
Review provided by Viator
K4620wochristinem
Aug 20, 2023
Okay - The views from the sailing vessel were wonderful. The tour would benefit from some historical narration rather than silly nautical songs and pretend pirate characters. You are on your own trying to figure out landmarks and such.
Review provided by Tripadvisor
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up to 15 guests
1 Adult
May 2024
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