Celebrate your special day on a private sailboat cruising Lake Michigan, with stunning skyline views and a customizable itinerary. Perfect for weddings and special gatherings!
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
4 hours
Fitness Level
Accessible for most guests, minimal physical activity required
Wildlife
History
Lake Michigan has been vital to Chicago’s development as a port city and has hosted numerous historic events and vessel explorations.
Conservation
The company promotes environmentally responsible boating practices, including waste management and minimal disturbance to local wildlife.
On A Boat Sailing
Celebrate your special day on a private sailboat cruising Lake Michigan, with stunning skyline views and a customizable itinerary. Perfect for weddings and special gatherings!
On A Boat Sailing is a Chicago-based private charter company offering curated sailing and yachting experiences on Lake Michigan.
The company specializes in a range of private cruises including skyline sunset sails, lakefront sightseeing, swim-and-sail playpen outings, wedding and wedding-party charters, engagement and proposal cruises, Navy Pier fireworks cruises, and group yachting aboard larger vessels.
Trips operate aboard a fleet that includes a 37' sailboat, the S/V Dragonfly, and the larger Yacht Guppy for big groups. Each charter includes a USCG-certified captain responsible for navigation, safety briefings, and a professionally managed experience. Add-on services include premium drink packages with pre-ordered wine, champagne, beer, and seltzer, and guests are welcome to bring BYOB snacks and beverages on most cruises.
Bookings are designed for private groups seeking a tailored event on the water, from romantic two-hour engagements to four-hour celebration charters and three-hour fireworks cruises. On A Boat Sailing highlights clear departure logistics from Chicago waterfront locations and offers complimentary light snacks and select beverages on several trips. Safety and comfort are emphasized through certified captains, fully equipped yachts, and adherence to local maritime regulations. The business is positioned for authentic Lake Michigan experiences, delivering skyline views, swimming stops, and customizable itineraries for family gatherings, corporate outings, and special events. On A Boat Sailing provides transparent trip summaries, duration options, and vessel details so prospective guests can choose the best private charter for their occasion. Seasonal options.
Location
Chicago, IL
Departures on Lake Michigan
Boat Types
37' sailboat, S/V Dragonfly, Yacht Guppy
Multiple luxury vessels available
Private Charters
9 trip types
Designed for private groups
Certified Captain
USCG-certified
Safety and professional operation
Select a trip, confirm a USCG-certified captain, and customize drinks and itinerary for an unforgettable Lake Michigan charter.
Arrive Early
Make sure to arrive at least 30 minutes before your scheduled departure time for a smooth check-in.
Bring Sun Protection
Sunscreen, hats, and sunglasses are essential for comfort during daytime cruises.
Pack a Personal Cooler
Bring your own beverages and snacks in a small cooler for convenience and variety.
Check the Weather
Monitor weather conditions prior to the trip to ensure a safe and enjoyable experience.
Sun protection
Sunscreen and hats will keep you comfortable during sunny hours.
summer
Swimsuit
Ideal for swimming at the Playpen stop.
summer
Light Clothing Layers
Layered clothing for changing weather or cooler evenings.
Camera or Smartphone
Capture memorable moments of the cruise.