CHICAGO BOAT RENTAL FIELD GUIDE
Celebrate Against the Chicago Skyline Aboard the Gypsy Spirit — Boutique Yacht Charters for 25–50 Guests
A practical guide to private social, corporate, and special-event charters aboard the Gypsy Spirit, departing from Navy Pier with tailored hospitality, skyline and lake views, and indoor and outdoor gathering spaces.
Celebrate Against the Chicago Skyline Aboard the Gypsy Spirit — Boutique Yacht Charters for 25–50 Guests.
Angela’s Charters runs private-event yacht charters aboard the Gypsy Spirit, a boutique vessel designed for elevated social, corporate, and special-event gatherings. Each charter is tailored around food and beverage, music, timing and atmosphere so groups can enjoy the Chicago skyline, Lake Michigan and the Chicago River in a refined, private setting.
Highlights
Outing Highlights
Chicago Skyline Experience
The Gypsy Spirit places guests in prime position for skyline and lakefront views—sunsets over Lake Michigan and the city’s architecture are central to the onboard experience.
Professional, Hospitality-First Service
Charters are run by a professional crew focused on refined hospitality, allowing hosts to relax while the team manages food, beverage and event flow.
Indoor and Outdoor Gathering Spaces
The yacht provides both sheltered interior areas and open-deck spaces so events can feel intimate or social as needed across changing weather and light.
What the day feels like
What the Charter Feels Like
A private charter aboard the Gypsy Spirit is calibrated to the event: curated food and beverage packages, tailored music and timing, and attentive service create an elevated but relaxed atmosphere for birthdays, anniversaries, client entertainment or milestone celebrations against Chicago’s waterfront.
Suitability
Who it's for
Who this charter suits — and who should check restrictions before booking.
Practical planner
Details to review before reserving
Charters emphasize hospitality with curated food and beverage packages, staffed service, and both indoor and outdoor gathering areas for flexible event flow.
Food, beverage and music options are curated and coordinated by the charter team to match the event’s tone; hosts work with staff to finalize details.
The vessel provides sheltered indoor spaces as well as open decks; plan attire appropriate for a waterfront evening and the formality of your event.
Review cancellation policies before reserving.
Frequently asked questions
Planning Your Outing
How long is a typical charter?
Charters typically run between 2 and 4 hours.
Where do charters board?
Charters depart from Navy Pier.
How many guests can the Gypsy Spirit accommodate?
Charters are configured for groups of roughly 25–50 guests.
Can guests smoke onboard or swim from the yacht?
The vessel is non-smoking and swimming from the yacht is not permitted.
Are pets allowed on board?
Pets are not allowed; contact the operator only for extenuating circumstances and special arrangements.
Is catering provided?
Curated food and beverage packages are available and coordinated by the charter team as part of the event planning.