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.
A More Elevated Way to Celebrate
Angela’s Charter Service offers luxury social event yacht charters in Chicago designed for guests looking to create meaningful experiences in a setting that feels private, refined, and memorable. Departing from Navy Pier, the Gypsy Spirit provides a boutique atmosphere for celebrating life’s moments against the backdrop of Lake Michigan, the Chicago River, and the city skyline.
Whether planning a birthday celebration, anniversary, engagement party, family gathering, reunion, or sunset cruise with friends, our private charters are designed to feel welcoming while maintaining an elevated hospitality experience. Rather than a typical party boat atmosphere, we focus on creating intimate social experiences where guests can relax, connect, and enjoy Chicago from the water in a more personal and sophisticated way.
Designed Around Your Experience
Every social charter aboard the Gypsy Spirit is thoughtfully tailored to fit the style and energy of your event. From curated food and beverage packages to music, atmosphere, and timing, our team works closely with guests to create an experience that feels seamless from start to finish.
Our spacious yacht offers both indoor and outdoor gathering spaces, allowing guests to enjoy the skyline, lakefront sunsets, and iconic Chicago architecture while comfortably entertaining friends and family. Whether your event is relaxed and intimate or lively and celebratory, we help create an environment that feels effortless, polished, and unforgettable.
Luxury Hospitality on Chicago’s Waterfront
For more than 30 years, Angela’s Charter Service has created elevated private yacht experiences centered around hospitality, thoughtful service, and unforgettable moments on Chicago’s waterfront. Aboard the Gypsy Spirit, guests enjoy a refined and welcoming atmosphere designed for luxury social events, private celebrations, and memorable evenings on Lake Michigan and the Chicago River.
Perfect for
- Birthday Parties
- Anniversary Celebrations
- Engagement Parties
- Family Gatherings
- Reunions
- Cocktail Parties
- Friends & Social Gatherings
"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.”