Chicago Skyline Sunset Sail

Experience a breathtaking Chicago sunset sail on the iconic Tall Ship Windy. Enjoy live Blues music on Monday nights. Book your unforgettable evening now.

Duration: 1 hour, 15 minutes
Cancellation: 1 day learn more
Highlights
  • Navy Pier - 148’ Tall Ship Windy departs from historic Navy Pier, the entertainment venue in Chicago
  • Lake Michigan - Tall Ship Windy will sail from Navy Pier into Lake Michigan and at the perfect time, turn so our guests may see the glorious sunset behind the Chicago Skyline.
  • Chicago Skyline - As you sail on Tall Ship Windy, guests will have a phenomenal view of the Chicago Skyline.
What's Included
  • On-board WiFi
  • Goods and Services Tax (GST)
  • Landing 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. Please arrive 20-30 minutes prior to departure.
Cancellation Policy

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

Customer Ratings
4.5
(50 Ratings)
5 stars
4 stars
3 stars
2 stars
1 star
Kristina_s
Aug 11, 2024
Trip ending show stopper - This was a great way to end my trip. I love Chicago. I'll be back and will definitely do this again.
Review provided by Viator
Chris_b
Jul 30, 2024
Perfect Chicago Sail at Sunset - Nice experience! The crew was fantastic. Both professional and friendly especially with children. If you’re looking for a nice simple sailing experience this is a great experience on a tall ship!
Review provided by Viator
Paul_t
Jul 29, 2024
Laid back sunset sail - What a great feeling when the sails go up and the captain turns the engines off. Enjoyable laid back excursion. Crew were great too.
Review provided by Viator
77777777777779
Jul 27, 2024
Perfect end to a long day. - After a 13 hour journey to reach Chicago from Manchester, this trip was a perfect ending to our day. Even tho we were tired after a long journey, this trip woke us up. The views of the skyline & sunset were amazing. The crew were very friendly and showed their skills putting the sails up & down. It is very much worth a visit if in Chicago.
Review provided by Tripadvisor
Hannah_w
Jul 14, 2024
Relaxing and fun - We had a big group and they made it tons of fun! Bar on board was great. Beautiful views of the skyline. One of the crew members Connor made it lots of fun!
Review provided by Viator
Don_g
Jul 14, 2024
Wonderful experience - Wonderful experience, beautiful evening. Captain and crew were spot on and very entertaining. A must do if in Chi town
Review provided by Viator
Tammy_e
Jul 8, 2024
Relaxing - Smooth experience. Suggest to anyone that has never sailed. Beautiful scenery. Professional pirates on board!!!
Review provided by Viator
J9884izjuanc
Jul 7, 2024
Awesome sailing on the Tall Ship Windy - The friendly and efficient crew took us on a wonderful sailboat ride. Awesome views of the lake and of the skyline. Planning to go back!
Review provided by Tripadvisor
Sarina_w
Jul 22, 2024
Average at best - It was just okay. Seating wasn’t comfortable, music wasn’t enjoyable. Not recommended if you’re looking for a romantic boat ride. Maybe good for families with kids who want the experience of riding a sailboat.
Review provided by Viator
Susan_w
Jul 10, 2024
This cruise was cancelled... - This cruise was cancelled because of remnants of hurricane Beryl. The weather was rainy, windy, and the lake was very rough!
Review provided by Viator
Select Date and Tickets
up to 15 guests
1 Adult
September 2024
Sun
Mon
Tue
Wed
Thu
Fri
Sat
Today