On A Boat Sailing
Luxury Sailing Adventures Along Chicago's Lakefront
📍Navy Pier Marina - Downtown Chicago
All bookings protected by our "Golden Sail" Money-Back Guarantee
What makes On A Boat Sailing different?
If you appreciate attention to detail, hospitality, and luxury amenities, this is the group booking for you! Our Chicago sailboat charters & cruises have been enjoyed by thousands of guests since we started in 2018. As we hit the waterfront for our 8th season, we pride ourselves on offering an unforgettable way to experience Lake Michigan from the City.
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!
This isn't like other boat rentals. Our custom charters go above and beyond to provide luxury and comfort for your group. On top of world-class sailing
700+ PRIVATE SAILING CHARTERS SINCE 2018
Trusted superhost to thousands of guests, each & every year.
Check out our luxury sailing experiences with this reel:
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 our 37' luxury sailboat, Dragonfly.
Bookings include:
🥂 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 $1,199
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 $899
Up to 7 guests
WEDNESDAY'S 6:30pm • SATURDAY'S 7:30pm
Real reviews from actual guests:
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 our 37' luxury sailboat, 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 $899
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 $899
Up to 7 guests
FRIDAY'S & SUNDAY'S
Departing 6:30pm
Three easy steps to pre-book your private boat party for summer 2025:
STEP 1 - Choose Your Adventure
Browse our all charters & cruises page to choose the experience that suits you.
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 auto-debited 5 days ahead of reservation.
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
