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    Cap'n Katie and her birthday squad
    "Just Be"
    Roomy and comfortable!
    Last sail before the veil!

    Bareboat Sailing Catamaran in Chicago, Illinois

    16 reviews
    44 bookings
    2 hours minimum

    Sail with us and enjoy the beauty of Lake Michigan and the magnificent Chicago skyline aboard our spacious sailing catamaran! Rates as low as $650 per hour for up to 13 passengers and a minimum booking of 2 hours. (Per Coast Guard Rules you must hire a Captain from our provided list or supply your own). Also, ask about our value-priced, 6-passenger sail with Captain included. You and your guests will enjoy our wide-open cushioned foredeck seating, relaxing comfy couches under the bimini, and our unique slingback chair off the stern.    Onboard 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, and a Bluetooth sound system to set the mood. You can BYOB and food or 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!   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 from the dock.  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 not included.
    Trip may require hiring additional qualified personnel.
    13 guests
    Cruising Catamaran
    Captain Russell

    Owner:Captain Russell

    Bringing you our love of sailing along the magnificent Chicago Skyline. Sail with us and sail 1st Class!

    Check Availability


    16 reviews

    5.0 out of 5!

    • Listing Accuracy

    • Departure & Return

    • Vessel & Equipment

    • Communication

    • Value

    • Itinerary & Experience

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    37 photos have been added by reviewers who booked this listing.
    1. ND

      Captain Brian was so helpful when some of our group experienced sea sickness. He was super fun to be around and made the trip so great!

    2. Judith

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

    3. Josh

      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.

    4. AS

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

    5. Julia

      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.

    Features & Details

    • Bluetooth
    • Life jackets/required safety gear
    • Cabin
    • Toilet
    • Wheel steering
    • Bimini
    • Chart Plotter
    • Twin Engine
    • 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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