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.
