On A Boat Sailing
Luxury Sailing Cruises & Charters
📍 Departing From 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 and First Mate Cait are world-class sailors. Their resumé includes a 9-month, 6,000 nautical mile voyage from Chicago to the Bahamas and back from October 2020 to July 2021 completing "America's Great Loop". They share their passion for sailing and affinity for Lake Michigan with guests every year.
Enjoy VIP amenities aboard our french-built, 37' luxury sailing yacht, S/V Dragonfly.
Dragonfly, a 2003 Jeanneau Sun Odyssey, offers the flexibility of adventurous sailing with the option to drop anchor & swim or float on The Lake or in the Playpen. Passenger amenities include spacious seating, Bluetooth surround-sound speakers, complimentary ice, beverages, snacks, a private bathroom with rinse shower, changing rooms, pool floats and Lilly Pad.
We're still perfecting the art of luxury sailing experiences in Chicago. Let us show you!
This isn't like other boat rentals that provide barebones and an old salty captain. Our custom charters go above and beyond to provide luxury, comfort and style for your group. No request is too small. Want to decorate the boat for a party or proposal? We do that and more while matching the energy and vibe you are looking for on the boat!
800+ PRIVATE SAILING CHARTERS SINCE 2018
Trusted superhost to thousands of guests, each & every year.
Check out our sailing experiences in action:
This 4-hour, all-inclusive group sailing adventure is our best seller for Summertime Chi birthdays and bach parties! Enjoy world-class sailing paired with a private swim & float party aboard our 37' luxury sailboat at the infamous Playpen or more secluded private anchorage on the Lake.
Bookings include:
🥂 Complimentary Champagne Toast
🥜 Unlimited Snacks & Non-Alcoholic Beverages
🍻 BYOB + Fully-Stocked Ice, Beers & Seltzers
🦩 Access to All Floaties & Rafts
🛎️ Fresh Towel Service
Starting at $1199
12 Guests pricing available
FRI • SAT • SUN
Departing 10am & 2:30pm
Navy Pier Marina, Downtown Chicago
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 $999
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 $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 $899
Up to 7 Guests
THU • FRI • SUN
Departing 6:30pm
This 2-hour private sailboat cruise will take you & your loved one on a favorable sail along the gorgeous Lakefront, giving a unique experience of seeing the city from the water. If you're looking for the perfect place to pop the question or take incredible photos - this is the cruise for you. Expect:
🌆 Clear views of Chicago's iconic skyline
⛵ The waterfront experience in style, comfort & class
📸 Professional photographer upgrade available
Starting at $799
Up to 7 Guests
WED • THU • FRI • SUN
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
