On A Boat Sailing
Luxury Sailing Charters & Cruises - Chicago, IL
500+ 5-star reviews
All bookings backed by our "Golden Sail" Money-Back Guarantee
On A Boat Sailing is the premier purveyor of sailing charters & cruises for small group celebrations in Chicago.
New for 2025! All bookings depart from and return to Navy Pier Marina.
700+ PRIVATE SAILING CHARTERS, INCREDIBLE REVIEWS
Trusted superhost to thousands of guests, each & every year.
What Makes On A Boat Sailing Different?
25+ years of sailing experience means smooth sailing for guests.
Captain Greg Scannell and First Mate Cait Scannell are world-class sailors. Their resumé includes an 8-month, 5,500 nautical mile voyage from Chicago to the Bahamas and back in 2021. They share their passion for sailing and affinity for Lake Michigan with guests every year.
Enjoy VIP amenities aboard our french-built, 37' sailing yacht, S/V Dragonfly.
Dragonfly offers the flexibility of adventurous sailing with the option to drop anchor & swim or float on The Lake. Passenger amenities include full access to upper and lower cabin seating, ample fridge space, and a private bathroom.
We're still perfecting the art of luxury sailing experiences in Chicago. Let us show you!
Whether you're celebrating a birthday, throwing a bach party for your bestie, or getting the crew together for a memorable day on Lake Michigan, our team is dedicated to making your experience as special as possible.
Guests love for our carefully-curated sailing experiences, VIP amenities, and boutique approach to private sailing charters.
This 4-hour, 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
🍻 BYOB + Fully-Stocked Ice, Beers & Seltzers
🦩 Access to All Floaties & Rafts
🛎️ Fresh Towel Service for All Guests
Starting at $1,399
Up to 7 Guests
FRI • SAT • SUN
Departing 10am & 2:30pm
Looking to Sail & Swim with more than 7 guests?
Check out Sailing Chi's Sail & Swim+ for more time on a larger boat with a bigger group of your friends!
This 3-hour, all-inclusive sail & sip cruise begins with sunset sailing along Chicago's famous skyline, with optional night swimming and concludes with a VIP viewing of the famous Navy Pier fireworks show. Bookings include:
🥂 Complimentary Champagne Toast
🥜 Unlimited Snacks & Non-Alcoholic Beverages
🍻 BYOB + Fully-Stocked Ice, Beers & Seltzers
Starting at $1,099
Up to 7 guests
WEDNESDAY'S 6:30pm • SATURDAY'S 7:30pm
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 Chicago's iconic architecture
⛵ The waterfront experience in style, comfort & class
📸 Unlimited snapshots to get the perfect summer profile pic
Starting at $999
Up to 7 guests
WED • FRI • SUN
Departing 3pm & 6:30pm
This 2-1/2 hour private sailing cruise promises breathtaking views of our nightly summer sunset aboard Dragonfly. Enjoy the sights & sounds of Lake Michigan at sundown, including:
🌇 Unbelievable views of Chicago's historic skyline
📷 Incredible lighting to get the perfect summer pic
🌅 Golden hour like you've never seen before
Starting at $999
Up to 7 guests
FRIDAY'S & SUNDAY'S
Departing 6:30pm
Golden Sail Money-Back Guarantee
Bad weather? Unexpected issues? We recognize things come up. Our money-back guarantee ensures you have the freedom to make adjustments with ease, providing peace of mind in the weeks and days leading up to your planned outing with us.
100% Refund up to Two Weeks From Departure
50% Refund up to 48 Hours From Departure
Full Refund for Weather Related Cancellations
Swap Dates With No Fees
Subject to Availability
Three easy steps to pre-book your private boat party for summer 2025:
STEP 1 - Choose Your Adventure
Browse our all charters & cruises page. We offer something for everyone!
STEP 2 - Recruit Your Crew
Fire up those group chats and start recruiting. Summer weekends will sell out.
STEP 3 - Lock-In Your Big Day
Book with a 50% fully-refundable deposit. Remaining balance to be paid at end of experience.
