Social Event Charters
Celebrate life’s memorable moments aboard the Gypsy Spirit with a private social charter designed around connection, atmosphere, and the Chicago skyline. From birthdays and anniversaries to sunset gatherings and intimate celebrations, each experience is tailored to feel elevated, effortless, and unforgettable.
Corporate Event Charters
Host your next corporate event aboard the Gypsy Spirit with a private charter experience designed for client entertainment, team gatherings, networking events, and executive outings. Combining refined hospitality with Chicago’s iconic waterfront, our corporate charters create a memorable setting that feels both professional and elevated.
Special Event Charters
Mark life’s biggest milestones aboard the Gypsy Spirit with a private charter experience designed to feel intimate, refined, and unforgettable. From engagements and rehearsal dinners to graduations and once-in-a-lifetime celebrations, each special event is tailored to create meaningful moments against the backdrop of Chicago’s skyline.
"What a fantastic party on the beautiful Free Spirit cruise...my husband was thrilled with his surprise party! First of Angela the owner is wonderful to work with, she is great with emails. The entire crew were sweet and hospitable to our guests. We had a blast with the open bar, food and dancing."
Padma A.
Chicago IL"An unforgettable and relaxing experience with incredible skyline views, welcoming crew, and great food. The perfect way to gather with friends and family while enjoying an intimate and peaceful cruise through Chicago."
Nikki E.
Chicago IL“From seamless planning and attentive service to incredible skyline views and a relaxing atmosphere, the entire experience aboard the Gypsy Spirit exceeded expectations. A perfect setting for corporate gatherings, private events, and unforgettable evenings on the water.”
Bernadette N.
Burbank CA- “From thoughtful planning and attentive service to unforgettable skyline views and a seamless onboard experience, the Gypsy Spirit created the perfect setting for a milestone celebration. Guests described the evening as relaxing, unique, and truly unforgettable.”
Laura P.
Chicago IL - “From the planning process to the experience aboard the Gypsy Spirit, every detail felt seamless, welcoming, and unforgettable. With exceptional hospitality, stunning skyline views, and an attentive crew, the celebration exceeded expectations and created a truly memorable evening on the water.”
Abigail H.
Chicago IL “An unforgettable celebration filled with exceptional hospitality, attentive service, and beautiful views of the Chicago skyline. From the curated catering to the relaxing atmosphere aboard the Gypsy Spirit, every detail created a memorable experience for family and friends.”
Juliet H.
Chicago IL“An intimate and unforgettable experience with incredible skyline views, delicious food, and a welcoming crew that made every guest feel comfortable from the moment they stepped aboard. The Gypsy Spirit created the perfect atmosphere for reconnecting, relaxing, and enjoying meaningful time with friends and family on the water.”