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
“We had a wonderful experience with Angela’s Charter Service for a client event. The boat was beautiful, extremely clean, and very well maintained — even the bathroom was spotless! The owner was there and was incredibly friendly and welcoming. The entire staff, including the captain, was professional, helpful, and made everyone feel comfortable. Most importantly, we felt very safe and secure throughout the entire experience. It was a fantastic experience from start to finish, and I would definitely recommend Angela's Charter Service for anyone looking for a great boat charter. We had a wonderful time!”
Michele Katz