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Some departure times on this date are still available.
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Some departure times on this date are still available.
Experience Chicago from a perspective few people ever do. Step aboard the Gypsy Spirit, a beautifully appointed private yacht docked at Navy Pier Marina, and enjoy an unforgettable cruise along Chicago's iconic lakefront and skyline. Perfect for birthdays, anniversaries, family gatherings, reunions, engagement celebrations, bachelorette parties, sunset cruises, and special occasions, the Gypsy Spirit accommodates up to 49 guests and offers multiple decks for relaxing, socializing, and taking in the views. Cruise Lake Michigan while enjoying: - Stunning skyline views - Front-row access to fireworks and special events - Spacious indoor and outdoor gathering areas - Sound system - Bar Packages Available - Catering Provided - Professional captain and crew Popular experiences include: - Sunset Cruises - Chicago River and Lakefront Cruises - Fireworks Cruises - Birthday Celebrations - Family Gatherings - Bachelorette Parties Client Entertainment and Networking Events Departing from Navy Pier Marina, the Gypsy Spirit offers a unique way to experience Chicago's architecture, waterfront, and world-famous skyline. Whether you're celebrating a milestone or simply gathering your favorite people together, we'll help create an experience your guests will remember long after they step off the boat.

CC
Angela and her staff are wonderful people who created a wonderful experience. We are so grateful for her fast and effective communication and willingness to work with our tight timeline. They went above and beyond and made the night unforgettable! 10/10 will book again
JB
A group of me and 20 friends had an absolutely fabulous time with Angela and her crew. We boated up and down the river and had a blast with each other dancing and tanning on the top deck. The crew was super helpful with everything including working the bar/kitchen preparing drinks and snacks during the charter. We will definitely book Angela again the next time we’re in Chicago. Thanks!
MC
Had the best time!!!
JH

You’ll get helpful information for your departure after your booking is confirmed.
Street Address For Arrival
Departure Location
Free cancellation up to 10 days before your trip.
BOARDING & CHARTER TIMES The Charterer is responsible for the timely boarding and departure of all guests. • Boarding begins 15 minutes prior to scheduled departure unless otherwise arranged. • Charter time begins and ends according to the agreement. • Additional time requested beyond the contracted charter period may result in overtime charges. The Captain and Crew reserve the right to adjust timing for safety, navigational, or operational reasons. GUEST CONDUCT The Charterer assumes responsibility for the conduct and safety of all guests. Guests agree to: • Follow all instructions provided by the Captain and Crew • Respect the vessel and onboard equipment • Conduct themselves in a safe and lawful manner Angela’s Charter Services reserves the right to terminate any charter without refund due to illegal activity, dangerous behavior, excessive intoxication, failure to comply with crew instructions, or possession of illegal substances onboard. The Charterer is financially responsible for any damage caused by guests. WEATHER & SAFETY The safety of guests and crew is the highest priority.The Captain reserves the sole right to determine whether weather or lake conditions are safe for departure and operation. • Charters may proceed dockside or along an adjusted route due to weather conditions. • No refunds are issued due to ordinary rain, wind, temperature, or weather-related conditions. • In the event severe weather prevents operation, Angela’s Charter Services may offer a rescheduled date at its discretion. FOOD & BEVERAGE Food and beverage service must be coordinated through Angela’s Charter Services or approved vendors. • Alcoholic beverages may not be brought onboard unless approved in advance. • Bar packages are based on confirmed guest count. • Dietary restrictions and allergy accommodations should be communicated prior to the event. SAFETY GUIDELINES For the safety of all guests: • No swimming permitted • Guests may not sit or stand on railings, furniture, or restricted areas • Children must remain supervised at all times • Children requiring life jackets must wear them while on exterior decks • Smoking is prohibited unless specifically permitted by crew • Proper footwear is recommended; high heels are discouraged Guests should immediately notify the Captain or Crew of any injury, illness, or emergency.