Chicago: Private Catamaran Sailing for up to 12 people

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This exclusive sailing experience includes breathtaking views of the Chicago skyline, refreshing swims, and the luxury of private yachting including Chicago’s largest chartered Catamaran.


  • Chicago's Largest Chartered Catamaran
  • Luxurious Amenities: Prepare to be pampered by our many onboard amenities.
  • Set sail and immerse yourself in the breathtaking beauty of the Chicago Skyline
  • Watch the sunset while sailing creates moments of tranquility & reflection


Make your next group outing an event they will never forget. Sailing out of Monroe harbor in the heart of Downtown Chicago, your adventure can host up to 12 people. This vessel is equipped with a full kitchen, grill, and floaty toys if you'd like to turn this into a swimming expedition. While we cannot supply drinks, we offer an option to BYOB at your discretion along with food to grill. We have coolers and a refrigerator available. Whether you're celebrating a special occasion, hosting a team-building event, or simply craving a day of relaxation and adventure, our catamaran promises an experience like no other. Book your voyage today and embark on a journey that will leave you with memories to cherish for a lifetime.


Our catamaran cruises are the perfect way for you to create some cherished moments with your friends and family. Sailing out of Monroe Harbor, Chicago on a 38' Luxury Sailing Catamaran (equivalent to a 70' monohull- more than enough room for your group) 13-person capacity* (We have options for 13+ please contact us for details.) Yacht Concierge who will cater to your group. Large Yeti Cooler and Refrigerator Full Kitchen (Galley) with working stove/oven Bluetooth Radio Barbecue Grill Floatie Toys for water fun Lessons, Tour, Chill Out, Party Cruise/ BYOB or combo It's all about customization.

Important Information

  • (If your group is over 6, you will be renting/bareboating this vessel. If you are not capable or do not want to skipper this vessel, you must hire a qualified operator. Coast Guard prohibits us from getting involved in this process but we are allowed to provide a list of qualified operators. We don’t know specifically what they charge but would estimate it would run a group of 13 an extra $9- $11 pp per hour)

Easy cancellation

Cancel up to 24 hours in advance for a full refund


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