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.
Celebrate Life’s Biggest Moments on the Water
Angela’s Charter Service offers luxury special event yacht charters in Chicago for guests looking to celebrate life’s most meaningful occasions in a setting that feels elevated, personal, and unforgettable. Departing from Navy Pier, the Gypsy Spirit provides a boutique private yacht experience designed around hospitality, atmosphere, and creating lasting memories on Lake Michigan and the Chicago River.
Whether planning an intimate wedding celebration, engagement party, rehearsal dinner, bachelor or bachelorette gathering, graduation, retirement party, or milestone birthday, every charter is thoughtfully customized to reflect the style and energy of your event. Our goal is to create experiences that feel refined and welcoming while giving guests a unique perspective of Chicago from the water.
Intimate Celebrations with Elevated Hospitality
The Gypsy Spirit offers a private and versatile setting for celebrations that deserve something more memorable than a traditional venue. With spacious indoor and outdoor gathering areas, skyline views, sunset backdrops, and curated food and beverage options, guests can enjoy an experience that feels both exclusive and effortless.
Our team works closely with guests, planners, and coordinators to help create a seamless experience from beginning to end. From atmosphere and timing to onboard hospitality and event flow, every detail is designed to help hosts fully enjoy the moment while creating an unforgettable experience for their guests.
Boutique Luxury on Chicago’s Waterfront
For more than 30 years, Angela’s Charter Service has specialized in elevated private yacht experiences centered around hospitality, professionalism, and personalized service. Aboard the Gypsy Spirit, guests can celebrate life’s biggest milestones in a setting that feels intimate, luxurious, and uniquely Chicago.
Perfect for
- Boutique Weddings
- Engagement Parties
- Bachelor & Bachelorette Parties
- Graduation Celebrations
- Retirement Parties
- Milestone Birthdays
- Anniversary Celebrations
"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.”