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Set sail!Captain Ray and crewmate CassidySet Sail with 36' Sailing Boat in Downtown, ChicagoSwimming!

Set Sail with 36' Sailing Boat in Downtown, Chicago

With Captain

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

Ray

54 total bookings
Capacity
6 guests
Sailing
Cruising Monohull

Reviews

5.0 (30 reviews)
  • Listing Accuracy

    Awesome
  • Departure & Return

    Awesome
  • Vessel & Equipment

    Awesome
  • Communication

    Awesome
  • Value

    Awesome
  • Itinerary & Experience

    Awesome
  1. Set Sail with 36' Sailing Boat in Downtown, Chicago
  2. Set Sail with 36' Sailing Boat in Downtown, Chicago
  3. Set Sail with 36' Sailing Boat in Downtown, Chicago
  4. Set Sail with 36' Sailing Boat in Downtown, Chicago
  5. Set Sail with 36' Sailing Boat in Downtown, Chicago
  6. Set Sail with 36' Sailing Boat in Downtown, Chicago
  7. Set Sail with 36' Sailing Boat in Downtown, Chicago
  8. Set Sail with 36' Sailing Boat in Downtown, Chicago
  9. Set Sail with 36' Sailing Boat in Downtown, Chicago
  10. Set Sail with 36' Sailing Boat in Downtown, Chicago
  11. Set Sail with 36' Sailing Boat in Downtown, Chicago
  12. Set Sail with 36' Sailing Boat in Downtown, Chicago
37 photos have been added by reviewers who booked this listing.
  1. DH

    Durward

    Ray and crew were exceptional. Pre cruise communication were perfect. Boat was great. This is a must do while in Chicago.

  2. hf

    hunter

    Excellent captain with a wonderful boat and personality. Highly recommend for lovers of sailing.

  3. 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.

  4. 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.

  5. 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

Ray

54 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

Make
S2
Model
11.0A
Length
36ft
Year
1982
  • Life jackets/required safety gear
  • Single Engine
  • Center Cockpit
  • Bimini
  • Wheel steering
  • 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
Approximate Location

Cancellation Policy

Full refund up to 14 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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