Angela’s Charter Service has spent more than 30 years providing luxury private yacht charters in Chicago, creating unforgettable experiences aboard the Gypsy Spirit on Lake Michigan and the Chicago River. Departing from Navy Pier, we specialize in elevated private charters for corporate events, client entertainment, milestone celebrations, social gatherings, and curated experiences designed around exceptional hospitality and personalized service.
More than a traditional Chicago yacht charter company, Angela’s Charter Service approaches every event with the mindset of a private yacht concierge. Our focus is creating custom experiences that feel polished, welcoming, and effortless from the moment guests step aboard. Whether hosting a corporate outing against the Chicago skyline, an intimate anniversary celebration, or a private sunset cruise with friends and family, every detail is thoughtfully planned to reflect the occasion and exceed expectations.
The Gypsy Spirit offers a boutique yacht experience that combines luxury, comfort, and the energy of Chicago’s waterfront. Our clients choose us not simply for a boat rental, but for an elevated atmosphere, attentive service, and the opportunity to experience Chicago from the water in a way that feels exclusive and unforgettable.
At Angela’s Charter Service, we are not focused on being a party boat. We are committed to delivering refined private yacht experiences in Chicago that are personal, memorable, and uniquely tailored to every guest aboard the Gypsy Spirit.
"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.”