NOW BOOKING SUMMER 2026
On A Boat Sailing
Luxury Charters & Cruises
Licensed & Insured
Up to 12 Guests
Privately book a luxury sailing yacht for an unforgettable day with your crew!
📍 Navy Pier Marina, Downtown Chicago
Our Chicago sailing charters & cruises are perfect for summer birthdays, bach parties, romantic proposals, anniversaries, and more. Take in the sights, sounds and breathtaking scenery of the Chicago Lakefront. From adventurous sailing to relaxing sunset cruises, swim & float parties, Navy Pier fireworks and plenty of special events throughout the year- we have something for everyone!
USCG Captain
CHICAGO SAILING EXPERIENCES starting at $799
800+ PRIVATE SAILING CHARTERS SINCE 2018
Trusted superhost to thousands of guests, each & every year.
ABOUT ON A BOAT SAILING
What makes us different?
On A Boat Sailing is a Chicago sailboat rental company that specializes in luxury sailing cruises and charters for up to 12 guests. If you appreciate attention to detail, hospitality, and comfortable amenities, this is the private group booking for you!
500+ 5-Star Reviews
Up to 12 Passengers
Easy Online Booking
Flexible Cancellation
25 YEARS OF SAILING EXPERIENCE
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.
LUXURY SAILING YACHT & AMENITIES
Dragonfly, a 2003 french-built Jeanneau Sun Odyssey 37, 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.
CUSTOM EXPERIENCES
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!
Our Guests Love Sailing With Us
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
No hidden fees. No surprise charges. 100% transparent pricing.
❌ NO damage/clening deposit
❌ NO refueling costs
❌ NO docking fees
