Bareboat Sailing Catamaran in Chicago, Illinois

15 reviews
36 bookings
2 hours minimum

Sail with us and enjoy the beauty of Chicago with your friends!  Rate as low as $650 per hour and a minimum booking of 2 hours. Ask about our value-priced 6 people Friday Happy Hour and Sunday Brunch cruises. Our spacious sailing catamaran provides the perfect setting for your group of up to 13 to enjoy summer fun and spectacular views of the city.!  With ample space, you and your guests will enjoy wide open foredeck seating, relaxing comfy couches in the shade and our unique sling back chair off the stern.    On board amenities include a private bathroom with toiletries in case you forgot, a massive cooler filled with ice to keep your drinks frosty or your food chilled, a Bluetooth sound system to set the mood, plus an experienced captain and crew to tend to your safety, and needs. BYOB and Food or take out the hassle and have Brix catering deliver boat sized snacks and platters right to the dock.  Whole Foods, Mariano's and Binny's also have catering options. And they deliver too!  From out of town?  Customize your dining experience with a "Taste of Chicago".  Plenty of local options that offer carryout or deliver.  Think Lake picnic! It's anchors aweigh, as we set off and cruise the lake, admiring the city skyline as we round Navy Pier in search of the playpen!  There we can drop anchor and relax while soaking in the Chicago sun ...can you say lake picnic? Dock Party! Want to keep the party going after the cruise, or just want to stay closer to land?  Ask about our dock party options.  Available anytime Sunday through Friday and after the last cruise on Saturday! We are located at 31st Street Harbor with nearby parking or curbside drop off just steps form the dock.  We can also arrange a pick up at Monroe Harbor when available. If you have any questions, we can answer those through GetMyBoat’s messaging platform before you pay. Just hit, “Request to Book” and send us an inquiry for a custom offer.

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


We want to bring our love of sailing and for the city of Chicago to others. Sail with us and sail 1st Class!

Check Availability

August 2021
September 2021
October 2021
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15 reviews

5.0 out of 5!

  • Listing Accuracy

  • Departure & Return

  • Vessel & Equipment

  • Communication

  • Value

  • Itinerary & Experience

31 photos have been added by reviewers who booked this listing.
  1. JL

    He was cool, made sure we were safe, had a great time.

  2. JH

    My friends and I have chartered a few boats here in Chicago, but this was by far the best experience we have had. We actually had to reschedule our initial cruise last minute due to bad weather. The boat owner, Russel, was very communicative and made the best of the not-so-great situation. He graciously offered to allow for our group to enjoy the boat for a lesser amount of time and stay at the dock. We were also able to reschedule for the following week and go out with Captain Brian at that time. Our group had such an amazing time during both sessions. We certainly had some strong personalities in the bunch (myself included) and Captain Brian was such a great sport. He was very professional but also blended in so well with our group that he was like another guest. We will without a doubt be reaching out to Russel & Captain Brian again for future events. Thank you both for making this such an unforgettable experience for us and our guests.

  3. AS

    Such a great boat! So much fun with Captain Brian!

  4. JP

    We had such a great time. The boat was better in person, and Captain Brian was awesome. I highly recommend him and 1st Class Charters (Chicago). Definitely worth it all around.

  5. AP

    Celebrated a birthday on the catamaran and it was hands down one of the best times! Captain Brian and Jess were the best! We will definitely be doing this again!

Features & Details

  • Life jackets/required safety gear
  • Bluetooth
  • Cabin
  • Toilet
  • Wheel steering
  • Bimini
  • Fuel type: Diesel
  • Berth
  • Head

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

Full refund is available up to 2 weeks prior to cruise date. Rescheduling is available due to weather after the refund period ends, up to 3 hours prior to cruise time. Captain/owner reserve the right to cancel, modify sail plan or end the cruise early for safety reasons including severe weather or heavy seas.  If weather conditions allow, we can party dockside and/or reschedule.   Special event dates may require special timing and considerations.  All groups of 7 to 13, are booked as a "bareboat charter".  A captain must be hired, by you, or a qualified operator obtained. We can provide a list of qualified captains, in case you do not.  Prices have captain, fuel, incidentals, etc. factored in, except gratuity for the captain/crew.

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