A Classic Yacht Experience with Timeless Character
Aboard the Gypsy Spirit, guests enjoy more than a private yacht charter—they experience one of Chicago’s most distinctive vessels on the water. This 1974 Chris-Craft Roamer classic brings a level of charm, character, and craftsmanship that simply can’t be replicated by newer boats. With its vintage design, spacious layout, and warm hospitality, the Gypsy Spirit offers a private charter experience that feels both elevated and unforgettable.
At 60 feet long and 16 feet wide, the Gypsy Spirit is fully United States Coast Guard approved to carry up to 49 passengers, making it an ideal setting for corporate events, milestone celebrations, client entertainment, and private gatherings on Lake Michigan and the Chicago River. The yacht features a spacious main cabin that comfortably accommodates 25 to 30 guests, a rear deck for 8 to 10 guests, and a forward deck for 10 to 15 guests, creating multiple spaces for guests to mingle, relax, and enjoy the skyline from different vantage points.
The upper deck, also known as the fly bridge, accommodates up to 21 passengers and offers an open-air setting for taking in the Chicago skyline, waterfront, and summer fireworks from the water. Onboard amenities also include both a men’s restroom and a women’s restroom, adding comfort and convenience for longer charters and private events.
Just as important as the vessel itself is the experience onboard. Every member of our crew is trained in CPR, first aid, and emergency response procedures, giving guests added peace of mind while enjoying their time on the water. From the yacht’s one-of-a-kind vintage character to the personalized hospitality that defines every charter, the Gypsy Spirit offers a private yacht experience in Chicago that is both memorable and uniquely its own.
