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We currently have 4 boats in our Chicago fleet. They are fast, comfortable, and built like tanks! We take pride in our sailboats and maintain cleanliness throughout.

The cockpits seat 6 so you can relax and take in the gorgeous views of downtown Chicago in style and comfort while sailing away on a private sailboat charter. We have comfortable cushions for lounging about in the sun, and a stereo with an iPod connection for your favorite tunes. We take care of our boats and they will take care of you. Our charter boats also provide glasses, plates, paper towels, flatware, ice, etc. Take a look below for details on each boat and click on each picture for more images.

Mystify

Have an urge for speed? Well then you’ve found the boat for you! Mystify is a Frers 33 and the perfect combination of a race boat and a cruising boat. Fast and comfortable! She is also the newest boat to our fleet. Mystify is one of our main sailing lesson boats and is equally at home taking out charters. We recommend 4 people for charters for ultimate comfort but we can definitely take out six like the rest of our boats. This lovely lady is also our main Groupon sailing lesson boat. She will sail 100 times in any given summer! She’s fast, comfortable, and a workhorse. Treat yourself to a sailing charter or lesson and let’s Go Sailing Chicago!

Sun of a Sailor

Ready for some fun in the sun? Come out and sail on Sun of a Sailor, a Pearson 34 sailboat. She is split equally between sailing lessons, sailboat charters, and Helm Time sessions here at Go Sailing Chicago as there isn’t much she can’t do right! Whether you want to learn the ropes, hang out in the sun and relax, or see the fireworks from the water, she will get you there safe and sound. Having sailed the entire length and width of Lake Michigan, Sun of a Sailor is ready to keep sailing. Come out and experience a piece of Chicago’s sailing history with one of our incredible captains. Click on the image to the right for more pictures and let’s Go Sailing Chicago!

FINS

Take a ride on the most popular built 30 foot production sailboat, ever. FINS is a Catalina 30 and truly a pleasure to sail. Once again, we have a boat completely in her element whether it be on a charter or a lesson. This boat can do it all. The design makes her feel so roomy it’s incredible. As you can see from the picture to the right, getting on FINS is a great time! As with all of our boats, she is ready to provide you with the Chicago sailing trip or lesson you’ve been waiting for. Click on the image to the right for more pictures of FINS.

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Obsession

Want to add a little luxury to your private Chicago sailboat charter? Then come take a ride on the aptly named, Obsession. At 42 feet in length and 14 feet wide, you will have all the room imaginable to hang out on deck and soak in the amazing views of downtown Chicago. When you sail on Obsession, you get an amazing captain and an additional crew member to take care of your every need. When we say luxury, we mean it. Come out and take a sail on one of the nicest boats on the water. You’ll be right at home sailing away on Obsession. Click on the image to the right for more pictures.

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Book by April 1 and receive $50 Off! Use promotion code 4113 at checkout.