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Set sail!Captain Ray and crewmate CassidySet Sail in Downtown ChicagoSwimming!

Set Sail in Downtown Chicago

5.0(20 reviews)
36 bookings
Estimated price
USD $250 / hour (2 hours minimum)


Super Owner

Summer fireworks every Wednesday at 9pm and Saturday at 10pm!  June 2nd through September 4th! Air and Water show August 20 & 21st!  Watch the fighter jets while sailing on the water!  It's absolutely the best seats in Chicago. Northerly Island Concerts- we recommend reserving 4 hours minimum so that we have time to drop anchor off Northerly Island Park and listen to the concert from the water!  Get away from the crowds and listen to the concert from your own private boat instead.  

Captain is included.
A captain is provided by the listing owner to host and operate the trip.
6 guests
Cruising Monohull

Check Availability


5.0 (20 reviews)
  • Listing Accuracy

  • Departure & Return

  • Vessel & Equipment

  • Communication

  • Value

  • Itinerary & Experience

  1. Set Sail in Downtown Chicago
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29 photos have been added by reviewers who booked this listing.
  1. BG

    Ray and Cassidy were very friendly, and allowed us to help sail the vessel as we requested. Ray is very qualified and enjoys sailing. I'm sure we could have laid back and relaxed as they did all of the work, but I think our experience was much better for having been more involved. Thanks, and we'll definitely use Ray again if we are back in the area and have the chance!

  2. JC

    Great boat, great captains. Highly recommend!

  3. Pamela

    Our sail with Ted and Tim was absolutely incredible. It was a perfect afternoon on the lake…only made possible by the attention and detail of this crew. We will be back!!

  4. Solomon

    I would definitely recommend sailing with Ray! He's very accommodating as he tailored the sailing route for my group's liking and he also helped coordinate a perfect time & view for my proposal. We had an awesome time!

  5. CC

    5 stars! Had a great time! The weather was perfect, and only to be be exceeded by the quality of the service! Thank you for the memories!



Super Owner

Summer in Chicago is short and sweet. So make the most of it with a USCG licensed captain on our boat Siren Song! Captain Ray, Ted, and Dawn will show you the Navy Pier Fireworks, Air and Water Show, and beautiful Chicago sights from our gorgeous sailboat. She was built in Holland, MI made for sailing the Great Lakes.

Features & Details

  • Air Conditioning
  • Bluetooth
  • Climate Control
  • Galley Stove & Oven
  • Life jackets/required safety gear
  • Berth
  • Fuel type: Diesel
  • Dodger
  • CD Player
  • Bimini
  • Wheel steering
  • Inboard Engine
  • Head
  • Toilet
  • Cabin

Approximate Location

You’ll get directions to the departure location when you make a booking.

The boat's approximate location on a map

Cancellation Policy

Full refund up to 10 days prior.

Additional Terms & Information

Weather happens! We're sailors - we get it.  Safety is our number one priority.  If we have to cancel due to bad weather, we will work with you to schedule another day and/or time. 

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