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!
Posted By : Dea_N
Ahoy! Celebrating the Class of 2024 on Windy was easy breezy and loads of fun with the professional crew and lively MC, er, tour guide. Would recommend for friend and family groups wanting to sail Lake Michigan, learn about Chicago architecture and listen to one of the best Trump impersonations ever! Arr matey!
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Posted On : 2024-05-30 18:24:50 
Posted By : Richa_B
Sunset sail was amazing- was incredible weather, staff was great and their was plenty of room to move around and get great pictures of the sunset
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Posted On : 2024-05-19 14:28:35
Posted By : Olga_P
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!!
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Posted On : 2023-10-01 02:30:27
Posted By : Meander04733761196
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!!
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Posted On : 2023-09-21 16:00:49 
Posted By : rogerhF9326SW
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.
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Posted On : 2023-09-21 12:21:24
Posted By : csseng1
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.
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Posted On : 2023-09-10 10:13:34
Posted By : Lynn_O
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!!
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Posted On : 2023-09-09 21:45:36
Posted By : Delilah_T
The crew, boat and evening were perfect. The crew was engaging and lively which added to the wonderful experience.
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Posted On : 2023-09-05 10:41:05
Posted By : Bonnie_F
Beautiful views, great music, peaceful boat ride! Definitely would go again! My family really enjoyed it!
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Posted On : 2023-09-05 10:21:26
Posted By : Barbara_S
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.
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Posted On : 2023-08-22 10:35:46
