On A Boat Sailing is the premier purveyor of sailing charters & cruises for intimate group celebrations in Chicago.
600+ PRIVATE SAILING CHARTERS SINCE 2018
Trusted superhost to thousands of guests, each & every year
Our private bookings are perfect for birthdays 🎂, bach parties 💍, engagements 💑, anniversaries ❤️, reunions 🥳, graduations 🎓, and more!
Unparalleled Sailing Expertise
Captain Greg Scannell and First Mate Cait Scannell share a combined 25 years of sailing experience, including an 8-month, 5,500 nautical mile voyage from Chicago to the Bahamas and back in 2021.
600+ private charters later, we're actively curating the best experiences for our guests looking to explore the joys of sailing on Lake Michigan.
Style & Comfort Aboard S/V Dragonfly
Our 37' sailing yacht is designed for entertainment & comfort. Guests love the flexibility of luxury sailing along with dropping anchor & swimming or floating with a cold one, should the weather permit.
Bluetooth connectivity to play your own summer hits, onboard bathroom facilities, and ample space above & below deck makes joining us for the day an absolute breeze.
Check out the about us page for more info.
Chicago Sailing Charters & Cruises
This half-day, all-inclusive group sailing adventure is our best seller for birthdays and bach parties! Enjoy world-class sailing paired with a private swim & float party aboard Dragonfly. Booking includes:
🥂 Complimentary Champagne Toast
🥜 Unlimited Snacks & Non-Alcoholic Beverages
🍻 Fully-Stocked Cold Beers & Seltzers
🛟 Access to All Floaties & Rafts
🛎️ Fresh Towel Service for All Guests
Starting at $1,399 for up to 7 Guests
FRI • SAT • SUN
Departing 10am & 2:30pm
This 3-hour private sailboat cruise will take you & your guests on a favorable sail down the gorgeous coastline of Chicago's lakeshore, all aboard Dragonfly. Expect:
-
Clear views of iconic Chicago architecture
-
Core memories for you & your friends to cherish
-
The waterfront experience in style & class
Starting at $999 for up to 7 guests
WED • FRI • SAT • SUN
Departing 10am, 1:30pm & 5:00pm
"10/10 experience - you are crazy if you DON'T book this. It was not your average crowded tour boat experience in Chicago. The dragonfly is an intimate vessel."
Laura, Grand Rapids, MI
This 3 hour all-inclusive sail & sip cruise begins with world class sailing along Chicago's famous skyline and concludes with a VIP viewing of the famous Navy Pier fireworks show. Bookings include:
-
🥂 Complimentary Champagne Toast
-
🥜 Unlimited Snacks & Non-Alcoholic Beverages
-
🍻 Fully-Stocked Cold Beers & Seltzers
-
🛟 Access to All Floaties & Rafts
-
🛎️ Fresh Towel Service for All Guests
Starting at $999 for up to 7 guests
WEDNESDAY'S 7pm • SATURDAY'S 8pm
This 3-hour private sailing cruise promises breathtaking views of our nightly summer sunset aboard Dragonfly. Enjoy the sights & sounds at sundown, including:
-
Unbelievable views of Chicago's historic skyline
-
Iconic architecture with majestic sights & sounds
-
Golden Hour like you've never seen before
Starting $999 for up to 7 guests
FRIDAY'S & SUNDAY'S
Departing 6:30pm
