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Welcome Aboard!

We currently have 4 boats in our 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 charter or sailing lesson.  We have comfortable cushions for loungin’ about in the sun, a private room for changing, 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. 

Mystify

Mystify is new to our fleet and an incredible 33 foot sailboat....info coming soon!

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 lessons and charters 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.  Now 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.  She is the smallest of our boats and you’d never know it as the design makes her feel so roomy.   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. 

Obsession

Want to add a little luxury to your private Chicago sailing charter?  Then come take a ride on the aptly named, Obsession.  At 42 feet in length and almost 14 feet wide, you will have all the room imaginable to hand out on deck and soak in the sun and amazing views of downtown Chicago.  Whether you want a fireworks cruise with friends, a romantic night with that special someone, or to enjoy the 2012 Chicago Air and Water show on one of THE nicest boats on the water, you’ll be right at home on Obsession.

Use our contact page, email, call, or even text us your reservation request!  773.710.7245 (SAIL).

And don’t forget our weekday sailing special!

Now Go Sailing Chicago!