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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.
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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.
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SERVICES
GO SAILING ON LAKE MICHIGAN THIS SUMMER!
World-class sailing, Great Lakes swimming & luxury amenities for you and your friends.
400+ REAL CUSTOMER REVIEWS
STEP ABOARD
Be first for private sailing offers & special event happenings on Chicago's famous Lakefront.
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