YOUR CHICAGO SAILING ADVENTURE STARTS NOW
We're a one boat, one captain operation sharing our passion for sailing with our customers. Our Chicago sailboat cruises have been enjoyed by thousands of guests since our first private charter in 2017. As we enter our 7th season, we pride ourselves on offering a safe & unforgettable way to experience Lake Michigan in the summer.
Captain Greg & 1st Mate Cait
We 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.
PLAN YOUR SUMMER SAILING TOUR OF CHICAGO!
Enjoy world-class sailing, Great Lakes swimming & luxury amenities with you and your friends.
This 3-hour Chicago 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 way to experience Chicago - this is the cruise for you.
Starting at $149pp for 6 guests
+ 6% booking fee
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 $149pp for 6 guests
+ 6% booking fee
AS FEATURED ON:
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, anchoring the boat in the party zone. Whatever you do - don't forget a bathing suit, some sunscreen & something cold to sip on!
Starting at $179pp for 6 guests
+ 6% booking fee
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 $129pp for 6 guests
+ 6% booking fee
“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
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