What you'll do:

Enjoy the best yachting experience with Chicago's sexiest captain! For starters our yacht Guppy is huge so no matter what the sea-state is her generous size and location in Chicago guarantees you will host a great party. Our captain is a passionate sailor but also goes out of his way to make this a memorable experience in the best way for everyone. We’ll soak up the fresh breeze from the lake and enjoy one of the world's great skylines. You couldn't ask for a more memorable experience than sailing in The Guppy along the Chicago coast!

Why we love it for your party:

Chicago’s best captain (He’s passionate about being out on the water and loves to pump up the party jams and enjoy the finest of yachting has to offer)
Stunning skyline views (Your group gets to cruise Lake Michigan on a luxurious 50-foot yacht Guppy, soaking in Chicago’s iconic skyline—perfect for photos and a memorable backdrop that elevates any celebration, from birthdays to bachelorette parties)
Customizable fun (Whether you want to anchor at the Playpen for swimming and music or sail past Navy Pier for fireworks, Sailing Chi tailors the trip to your vibe—ideal for keeping everyone in your group entertained and engaged)
Insta-worthy (Guppy has many lounge spaces for sunbathing and lake-gazing is available on the foredeck - a popular locale for photo opportunities on beautiful days!)
Spacious luxury (With room for your crew on a well-equipped yacht, there’s space to dance, relax, or mingle, plus amenities like a huge sound system for your best playlist—making it the best private party venue on the water)

About this experience partner:

At Sailing Chi, we emphasize client enjoyment, safety, and a tailored experience to bring only 5-star events for you and your guests. Yacht Guppy offers world-class sailing with comfortable amenities, encouraging you & your guests to enjoy the day ahead. Our professional captain handles everything, letting your group focus on celebrating—no stress, just good times, whether it’s a corporate outing or a family reunion.

Additional information:

We are BYOB but we also offer the ability to have the boat provisioned with all your favorites. Just let us know!
If you're interested in a more customized, special event, reach out to us directly and we can curate a unique experience for your party.

By Category

By Party Type

By Top Batch Cities

NEW! Batch Stays

NEW! Batch Stays