Taking Care of People on the Water Since 1997
Angela’s Charter Service offers something increasingly rare: one classic yacht, one private group and an experience planned with genuine care.
The Gypsy Spirit’s warm wood, comfortable gathering spaces and sweeping Chicago views give her a character that newer party boats cannot reproduce. When you charter her, the yacht, crew and itinerary belong entirely to you and your guests.
Meet Angela
Angela Motola entered the Chicago yacht charter business in 1997 as a single mother building a secure future for her daughter and creating something meaningful of her own.
Nearly 30 years later, she has welcomed guests from different cultures, countries and industries aboard Chicago’s waterways. She has hosted corporate events, birthdays, anniversaries, family gatherings, memorials and many of life’s most meaningful occasions.
Through it all, Angela has learned that the best experiences share the same ingredients: beautiful surroundings, thoughtful hospitality and uninterrupted time with people who matter.
Today, she is grateful to share the strength and tenacity of entrepreneurship across four generations of women in her family—including her granddaughter, Matilda, pictured above.
Personally Planned, Thoughtfully Hosted
When you reserve the Gypsy Spirit, you plan your charter directly with Angela—not a call center or anonymous booking department.
She takes time to understand your occasion and coordinates the details around your group, including the itinerary, food, bar service, entertainment and timing. On the day of your charter, Angela and her crew take care of the experience so you can relax and be present with your guests.
A New Chapter at Navy Pier
Angela’s Charter Service is beginning a new chapter aboard the Gypsy Spirit at Navy Pier, continuing the work Angela began in 1997: bringing people together and helping meaningful occasions feel effortless.
We are not a party boat, and we have never tried to be.
We offer a more personal experience—a classic yacht, attentive hospitality and nearly 30 years of knowing how to care for people on the water.
"What a fantastic party on the beautiful Gypsy Spirit...my husband was thrilled with his surprise party! First off Angela, the owner, is wonderful to work with; she is great with emails. The entire crew was 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.”