1. Bareboat Sailing Catamaran Charter in Chicago
  2. Bareboat Sailing Catamaran Charter in Chicago
  3. Bareboat Sailing Catamaran Charter in Chicago

Bareboat Sailing Catamaran Charter in Chicago

Our sailing cat is spacious enough for 20, but we are offering it up for your group of up to 13! Giving you and your guest ample space, you will enjoy wide open foredeck seating, our relaxing comfy couches in the shade or lounging in our unique sling back chair off the stern. On board amenities include private bathroom with toiletries in case you forgot, plush noodles for swimming, massive cooler filled with ice to keep your drinks frosty or your food chilled, Bluetooth sound system to set the mood, plus 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, Marianos and Binnys 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. 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 pick up at Monroe Harbor.

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


Having been boaters for most of their lives, Captain Brian and Captain Russell want to bring their love of sailing and for the city of Chicago to others. Sail with them and sail 1st Class!

Check Availability

March 2021
April 2021
May 2021
  • Select a date to check availability.

Features & Details

  • 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 5 days prior.

Additional Terms & Information

Payment due upon booking. Rescheduling available due to weather after the refund period ends. Special event dates may require special timing and considerations. For all parties of more than 6, the charter is a "bareboat" and a captain must be hired. We can provide a list of qualified candidates. All prices are "all inclusive" (except gratuity) and include captain, fuel, incidentals etc.

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