Celebrate love or a special moment with a luxurious water cruise. Find out why The Adventure Collective’s romantic sail is a must-do in the area.
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
2 hours
Fitness Level
Comfortable sitting is recommended, no physical exertion required.
Wildlife
History
This cruising area has been a hub for maritime trade dating back to the 1800s, with a rich history of sailing and exploration.
Conservation
The Adventure Collective emphasizes eco-friendly practices, including waste reduction and respecting local marine life during trips.
On A Boat Sailing
Celebrate love or a special moment with a luxurious water cruise. Find out why The Adventure Collective’s romantic sail is a must-do in the area.
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.
Book in advance
Reserve your spot early to ensure availability, especially for special occasions.
Check weather forecast
Plan your cruise on a clear day for the best experience and breathtaking views.
Bring a camera
Capture the stunning skyline and your memorable moments on deck.
Arrive early
Get comfortable and enjoy the scenery before setting sail.
Smartphone or Camera
Capture the stunning city views and special moments during the cruise.
Light Jacket
Bring a jacket in case of breeze or cooler weather on deck.
any
Comfortable shoes
Wear suitable footwear for boarding and moving around the boat.
Celebration items (optional)
Bring decorations or personal items to personalize your occasion.