Where do charters depart from?

Charters depart from Navy Pier in Chicago; confirm your exact meet-up location and boarding time with Angela’s Charter Service when you book.

What is the maximum guest capacity?

The Gypsy Spirit carries a maximum of 49 passengers for private events.

Can we bring our own food and alcohol?

Angela’s Charter Service offers curated food and beverage packages and can advise on bringing external items; contact the operator to coordinate corkage policies and catering needs.

Is the vessel wheelchair accessible?

Accessibility details are not provided in the listing—please contact Angela’s Charter Service directly to discuss specific mobility needs and accommodations.

Are pets allowed onboard?

Pets are not allowed except in extenuating circumstances; contact the operator ahead of time to request an exception.

What should we do about cancellation or weather?

Weather and cancellation policies vary by operator; check terms when booking and coordinate alternative dates with Angela’s Charter Service if conditions force a change.

Private Yacht Charter on the Gypsy Spirit: Celebrate with Chicago Skyline Views

On a warm evening, the Gypsy Spirit slips from Navy Pier and the city rearranges itself: towers line up like stage lights, the water opens into a broad sheet of deep freshwater, and conversations swell into a soundtrack for the skyline. Larger Private Events Yacht Charter is Angela’s Charter Service’s private social and corporate offering in Chicago that turns milestones into waterborne evenings. Departing from Navy Pier on Lake Michigan and weaving past the Chicago River, the yacht seats up to 49 guests and offers both enclosed salon spaces and open decks for skyline views and sunset photographs.

This is a charter built around hospitality. For more than 30 years Angela’s Charter Service has run refined private events on the water; the Gypsy Spirit pairs polished service and a professional crew with customizable menus, music, and timing to fit birthdays, anniversaries, engagements, reunions, and corporate gatherings. Events typically run two to four hours, and organizers are advised to arrive thirty minutes early for safety and boarding. The vessel is strictly non-smoking and does not permit swimming or pets except by prior arrangement.

What makes a Chicago yacht charter distinct here is the setting: the sweep of Lake Michigan’s freshwater, the jagged silhouette of historic and modern architecture along the lakefront, and the contrast of the river’s industrial bridges as you pass downtown. Photographers will find dramatic lines from Navy Pier toward the Hancock and Willis Towers; architects and planners will appreciate how the skyline compresses into a continuous horizon when seen from the water.

Practical details keep the celebration smooth. The Gypsy Spirit offers indoor and outdoor gathering spaces to shelter guests from wind and weather while keeping the city in sight. The crew handles navigation, safety briefing, and basic hospitality so hosts can focus on their guests. Capacity limits and coordinated catering make the yacht a more intimate alternative to large party boats.

A brief historical note: Navy Pier first opened in 1916, and its transformation into an events hub makes it a convenient, recognizable embarkation point for private charters. Whether you want a relaxed sunset cocktail or a formal corporate reception, this private yacht charter distills Chicago’s waterfront into an evening of thoughtful service, skyline theater, and uncomplicated celebration on Lake Michigan.

Hosts work directly with the Angela’s Charter Service team to tailor menus, timelines, and music so every detail reflects the event’s tone. Sunset departures maximize skyline glow, mid-afternoon cruises are quieter for family gatherings, and evening charters light the city for dramatic backdrops. For planners, the Gypsy Spirit simplifies logistics: professional crew, onboard restrooms, climate-protected interior, and flexible layout reduce coordination stress. With careful planning a private charter becomes an efficient, memorable extension of Chicago hospitality.

Private Yacht Charter on the Gypsy Spirit: Celebrate with Chicago Skyline Views

Adventure Brief

Keep the Adventure Going

Trip Details from the Operator

Frequently Asked Questions

Key Highlights

Local Insights

Related Adventures & Guides

Operated By

Adventure Tips

Recommended Gear