About Your Trip
Set sail from downtown Chicago with Captain Charles for a private sailing experience aboard a spacious 47.7' Beneteau sailboat. Whether you're looking to spend the afternoon relaxing at the Playpen, celebrate with friends, or take in the skyline after sunset, these trips are built around your group and the kind of day you want to have.
Daytime trips run between 11 AM and 5 PM, with two trips available each day. For an evening experience,
trips are available from 7 PM to 11 PM, giving you a chance to watch Chicago light up from Lake Michigan.
For the daytime Playpen experience, you'll depart from the heart of downtown Chicago and cruise out toward one of the city's most popular summertime gathering spots. Once anchored up, settle in and enjoy the boat, the views, and plenty of time to swim and relax. Water toys and floats are available for the group, while a powerful Fusion stereo system with speakers and subwoofers throughout the boat keeps your favorite music playing.
Captain Charles and his team put a major emphasis on hospitality. Depending on your trip arrangements, they can put together a spread with fruit, sandwiches, High Noons, Modelos, tequila, rum, and more. The goal is to tailor the experience to your group rather than make everyone follow the same itinerary.
Your 47.7' Beneteau offers plenty of room to spread out and enjoy the trip. The spacious cockpit is ideal for hanging out with your group, while the interior features a large salon, comfortable cabins, and a well-equipped galley. The boat combines the performance of a true sailing yacht with the comfort and amenities you want for a private Chicago charter.
Evening trips offer a different side of the city. Cruise Lake Michigan as the sun goes down, relax with friends, celebrate a special occasion, or simply enjoy the Chicago skyline from a completely different perspective. These charters are a great fit for anniversaries, proposals, birthdays, group celebrations, corporate outings, or an evening away from the crowds.
Captain Charles holds a United States Coast Guard 100-ton Merchant Mariner Credential and has built his trips around attentive, personalized service. He works to make each charter feel like your own, whether that means a lively afternoon at the Playpen or a laid-back evening sail past the skyline.
Come aboard, settle in, and experience Chicago from Lake Michigan with Captain Charles handling the details.
Amenities
Type
Boat Cruise, Booze Cruise, Sunset Cruise
Skill Levels
Beginner, Intermediate, Advanced
Beer
Feel free to enjoy responsibly, but please no glass.
Music
You can play your own bluetooth music.
Boat Restroom
This boat has a restroom.
Weather
You won’t lose your deposit if the trip is canceled due to weather
Kid Friendly
This trip can cater to small children.
Flexible Cancelation
This trip can be canceled up to 14 days before the trip.
Disability Friendly
This trip is not suited for those with disabilities.
Lunch
Please provide your own food / snacks.
