We use cookies to improve your browsing experience.

And dolphins make us happy. Find out more about our cookies policy here.

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

Set Sail with 36' Sailing Boat in Downtown, Chicago

5.0(28 reviews)
·
50 bookings
·

If you have any questions, we can answer those through GetMyBoat’s messaging platform before you pay. Just hit, “Send Booking Inquiry” and send us an inquiry for a custom offer. Siren Song is a spacious 36 foot sailboat built for cruising the Great Lakes. She prefers to sails rather than motor.

Starting from

$225/hour
Base Cost
  • $225/hr
    2 hrs min
Captain Included
The base cost includes the Captain.
Ray

Ray

50 total bookings
Superowner
Capacity
6 guests
Sailing
Cruising Monohull

Check Availability

Reviews

5.0 (28 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
36 photos have been added by reviewers who booked this listing.
  1. 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.

  2. 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.

  3. 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!

  4. Beth
    Beth

    I can’t say enough for how great my experience was with Captain Ray, Captain Dawn and Captain Ted. From the initial booking all the way through the actual sailing, they were responsive, accommodating and amazing to work with. My fiancé and I did our engagement photos aboard Siren Song and the experience and photos exceeded everything I dreamed this day and these photos could be. Highly recommend!

  5. LG

    Leigh

    Ray and Dawn were excellent, professional captains. We departed around 6pm and took a lovely sunset trip around the harbor. Unfortunately the winds were a bit too high to sail further out onto the lake, but we all appreciated the safe and relaxing trip. Highly recommend!

Ray

Ray

50 total bookings
Superowner

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

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 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. 

Similar Listings

Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois
Sailing in Chicago · 6 guests

Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

5.0
Superowner
Best of 2023
$220hour
Private Cruise onboard Hunter Legend Sailboat in Chicago
Sailing in Chicago · 6 guests

Private Cruise onboard Hunter Legend Sailboat in Chicago

5.0
Superowner
$200hour
37' Luxury Sailing Yacht in Downtown Chicago
Sailing in Chicago · 10 guests

37' Luxury Sailing Yacht in Downtown Chicago

5.0
Superowner
$200-$300hour
Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor
Sailing in Chicago · 3 guests

Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor

4.8
$115-$120hour
Charter this Beautiful Catalina 36 Sailboat w/Captain in Chicago, Illinois
Sailing in Chicago · 6 guests

Charter this Beautiful Catalina 36 Sailboat w/Captain in Chicago, Illinois

5.0
$225hour

Top Destinations Nearby