WHAT MAKES ON A BOAT SAILING DIFFERENT
We're a one boat, one captain operation sharing our passion for sailing with our customers. Our Chicago sailboat charters & cruises have been enjoyed by thousands of guests since our first private charter in 2018. As we enter our 7th season, we pride ourselves on offering a safe & unforgettable way to experience Lake Michigan.
Captain Greg & 1st Mate Cait
Our crew have a combined 25 years sailing experience, allowing us to curate the best possible experience for our guests. Sit back & relax as you take in the sights & sounds of Chicago's famous Lakefront.
2003 Jeanneau Sun Odyssey 37
S/V Dragonfly was built for day cruises & entertaining. Our 37' luxury sailboat is a fantastic venue for any special occasion. We are a fully-licensed commercial passenger vessel and operate under the highest safety standards monitored by the US Coast Guard.
Learn more about the crew & S/V Dragonfly here.
Simply the best escape from hot summer days in the city.
Discover the world of sailing on Lake Michigan!
Our focus is on curated experiences for small groups of up to 10 guests that prefer the privacy & flexibility of their own Chicago sailboat rental to explore and indulge in the beauty of being on the water along Chicago's Lakefront.
2024 bookings are available Wednesday, Friday, Saturday & Sunday from Memorial Day weekend to mid-October with multiple departures daily from centrally-located Monroe Harbor in Downtown Chicago.
Please visit our all charters page to learn more about our one-of-a-kind sailing adventures. Chicago is the best place to combine the thrill of sailing with views of a world class skyline- let us show you.
Cheers!
Captain Greg & First Mate Cait
OVER 500 PRIVATE CHARTERS IN CHICAGO SINCE 2018
OUR CRUISES & CHARTERS
NOW BOOKING - SUMMER 2024
This 3-hour sailboat cruise will take you & your guests on a favorable sail down the gorgeous coastline of Chicago's lakeshore, giving a unique perspective on the city's world-class architectural landscape. If you're looking for a private & intimate sailing experience Chicago - this is the cruise for you.
Starting at $899 for 6 guests
WED • FRI • SAT • SUN
10am-1pm, 1:30pm-4:30pm, 5:30pm-8:30pm
Relax and enjoy a captained sunset cruise on our sailing yacht, a Jeanneau Sun Odyssey 37. We will cast off from Monroe Harbor in downtown Chicago and set sail to a favorable course on Lake Michigan. Bring your own food and drinks, listen to your favorite music, and take in the views of our city’s iconic skyline from the Lakefront.
Starting at $899 for 6 guests
FRI • SUN
6:30pm-8:30pm
Chicago's famous lakefront party is back. This 4-hour private sailboat charter is designed for you & your friends to party in luxury. We will depart from Monroe Harbor, with a good mix of adventure sailing on Chicago's Lakefront along with dropping anchor at the Playpen or a private area of your choosing. Whatever you do - don't forget a bathing suit, some sunscreen & something cold to sip on!
Starting at $1,099 for 6 guests
FRI • SAT • SUN
10am-2pm, 2:30pm-6:30pm
This 2.5 hour Chicago sailboat cruise will split your time us between sailing the city's famous Lakefront & eventually making our way to the famous Fireworks show at Navy Pier. These are the best seats you can possible have for a world-class fireworks show. We've all seen fireworks - you've never seen anything like this before.
Starting at $799 for 6 guests
WED 7pm • SAT 8pm
“I rented [Dragonfly] to celebrate my bday with 6 close girlfriends. Greg was very communicative before the trip. He answered all my questions in a very timely manner. The boat is very spacious!
Dyna, Chicago, IL
STEP ABOARD
Be first for private sailing offers & special event happenings on Chicago's famous Lakefront.Â