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With Captain
Easygoing sail with a relaxed, scenic vibe, where guests soak in Chicago’s skyline from the lake and leave wanting to come back.
Well‑kept sailboat praised for its comfort and condition, giving small groups space to unwind while the crew handles all the sailing.
Guests highlight professional yet laid‑back captains with excellent communication, strong sailing skills, and a knack for reading the group’s vibe.
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AI Overview
Owner's Description
ABOUT THE TRIP Embark on an unforgettable boating experience and explore the stunning beauty of Chicago’s skyline from the water. Whether you’re celebrating a special occasion or simply enjoying a relaxing day out, this 36' sailing boat offers unmatched views of the city and a serene atmosphere that promises tranquility on the water. Experience the perfect balance of adventure and calm as you cruise along the lake, taking in Chicago’s iconic skyline from a unique perspective. ABOUT THE BOAT Siren Song is a spacious 36-foot sailboat designed for comfortable cruising on the Great Lakes. Built with a preference for sailing over motoring, she offers an authentic and peaceful sailing experience. The boat’s design ensures plenty of room for relaxation while providing a smooth and enjoyable journey across the water. WHAT'S INCLUDED The boat rental includes a sailing experience with a skilled crew to guide you through the waters. Enjoy the spacious deck and comfort of a well-maintained sailboat as you take in the picturesque views of Chicago’s skyline. WHAT'S NOT INCLUDED Tips are not included, but are always appreciated. DEPARTURE LOCATION The departure location is Monroe Harbors public dock. OTHER THINGS TO KNOW Siren Song is perfect for those who want to experience the beauty of Chicago from the water, offering a relaxing and scenic outing. Whether you’re a seasoned sailor or new to boating, this experience provides a peaceful way to enjoy the city’s remarkable waterfront.
Ray
55 total bookings
- Capacity
- 6 guests
- Sailing
- Cruising Monohull
Reviews
(30 reviews)
Listing Accuracy
AwesomeDeparture & Return
AwesomeVessel & Equipment
AwesomeCommunication
AwesomeValue
AwesomeItinerary & Experience
Awesome
37 photos have been added by reviewers who booked this listing.
dr
david
Went on a 3 hour cruise with Captain Dawn and Ted and wow did we have a great time. It’s well worth it to see Chicago from the lake, and no better way to get out on the water than on a sailboat. Will definitely reach out to this group again when I return to Chicago.
SH
Susan
A wonderful May sail. Great boat for 6 people to relax and enjoy the city skyline, while Ray tends to the sailing. Very competent sailor and friendly.
RJ
Robert
Ray and Cassidy were great! We didn't have a planned route or destination so Ray chose his own and it was incredible! The views were amazing and we had the best seats in the house to the Air and Water show! Ray and Cassidy were both friendly and knowledgeable through the whole experience. We couldn't have asked for a better crew! The boat was beautiful and a couple of us even had a chance to steer it. All around amazing.
Yvette
We had an amazing time. I even spilled a little wine and they helped us clean it up quickly with no problems. The captain explained everything so easily. I’d definitely do it all over again. Thank you for a great experience!
BG
Bradley
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!
Ray
55 total bookings
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
- S2
- 11.0A
- Capacity: 6 people max
Safety Equipment
Life Jackets (1)
Guest Amenities
Cabins (1)
Sun Protection
Toilets (1)
Departure Location
You’ll get helpful information for your departure after your booking is confirmed.
Street Address For Arrival
400 East Monroe Street
Chicago, Illinois, 60601
United States
Departure Location
Cancellation Policy
Free cancellation up to 14 days before your trip.
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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