Elevate your boat trip with pre-ordered premium drinks, making every sail more luxurious. Discover how On A Boat Sailing adds convenience and class to your water adventure.
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
1–4 hours
Fitness Level
No physical fitness required; suitable for all ages
Wildlife
History
This region has a rich maritime history dating back over a century, with numerous local legends tied to its waters.
Conservation
The company practices eco-friendly boating and supports local marine conservation efforts to preserve the area's natural beauty.
On A Boat Sailing
Elevate your boat trip with pre-ordered premium drinks, making every sail more luxurious. Discover how On A Boat Sailing adds convenience and class to your water adventure.
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.
Plan your drink selection ahead
Pre-order your favorite beverages to ensure they're ready when you board, especially during busy weekends.
Keep drinks chilled
Utilize the provided ice packs and coolers to maintain optimal cold for your beverages throughout the trip.
Bring comfortable seating
Bring cushions or cushions for a more comfortable lounging experience while sipping your drinks.
Stay hydrated
Complement your alcohol with plenty of water to stay refreshed during sunny days on the water.
Sunglasses
Protect your eyes from glare while enjoying your drinks and the scenic views.
summer
Sunscreen
Prevent sunburn during your time on the water.
summer
Hat
Shade your face while relaxing on deck.
summer
Light Jacket
Stay warm during cool mornings or evenings on the water.
spring|fall