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YOUR CHICAGO SAILING ADVENTURE STARTS NOW
We're a one boat, one captain family business sharing our passion for sailing from Monroe Harbor in Downtown Chicago. Our chicago boat 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 get on 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
UP TO 10 GUESTS • BYOB • FLOATIES INCLUDED
GO SAILING IN CHICAGO THIS SUMMER!
Weekends are in high demand & filling up fast. Choose from a half-day party at the playpen, a 3-hour cruise along the Chicago Skyline or a Navy Pier Fireworks show from the actual best seats in the house. Any celebration is better from a floaty in Lake Michigan.
Our season kicks off Memorial Day weekend. Start planning with your crew now!
400+ FIVE-STAR REVIEWS
STEP ABOARD
Be first for private sailing offers & special event happenings on Chicago's famous Lakefront.
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