Private Sailing Charters

Sailing Chicago's beautiful lakefront offers an experience not to be missed and views of the skyline that can't be beat. Kick back and let our experienced crew treat you to a relaxing sail or if you're feeling more adventurous, take a turn at the helm -- we'll be there to ensure a safe and fun experience.  Whatever your choice, our exclusive sailing charters are tailored to your preferences.  Our mission is to provide safe, enjoyable, customized sailing adventures for our customers.

GLSS Solo Mac Chicago Start

The GLSS Solo Mac racers will soon begin their 333 mile journey from Chicago, IL to Mackinac Island, MI.  This singlehanded sailing regatta is celebrating its twentieth anniversary this year.  Each sailor races his/her sailboat, alone, 24 hours a day to the finish line at Mackinac Island.  Capt. Mike has competed in the last three editions of this race, but will be cheering on his fellow sailors from his home port of Chicago this year.  Find out more about this unique challenge at the GLSS Website.  During the race you can track the sailors online.  And, YES, Capt. Mike is a GLSS member. ;-)

Good luck to all of the racers!!
708-824-SAIL or Info@ComeSailing.us

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We had an excellent charter with Michael! A group of girl friends and myself went for a weekend afternoon charter and had a blast sailing along Lake Michigan! They have every accommodation on board (cooler, restroom, seating area, below deck seating) that you could need for a sail. Michael and his crew were professional and friendly to sail with- I highly recommend booking your charter here!

Robyn Szablewski - Facebook Review

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I recently went on an afternoon charter with some friends on Bernard with captain Michael, it was amazing! Michael made our group feel comfortable, safe, and helped make our time on the lake very memorable. This is the boat you want to be on to have a great time sailing along one of the world's prettiest skyline views! I would highly recommend them!

​Jamie Delos Reyes - Facebook Review

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Had a WONDERFUL birthday sailing with my family and Captain Mike was friendly and knowledgeable!!...we will definitely be sailing with him again!!#bestbirthdayever!!

​Shawn Jeffries- Cullens - Facebook Review

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Captain Mike took us out mid day and we have a beautiful day for sailing. He was so accommodating to us. He was there but you barely knew it. The boat was clean & he had refrigerator space and ice for us. We packed like we were going to two days, not two hours, and the boat didn't seem crowded. We had so much fun and can't wait to go out again! Thank you Come Sailing! Also - an added bonus is that if you park in the Millennium .....

Colleen L. - Yelp Review

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​Captain Mike made or experience so easy and amazing! We were a bit confused where to go on arrival, but another friendly boater gave us a lift to Mike's sailboat. We rented Mike's sailboat for our friends 26th birthday for a few hours on a sunny Monday, and we already cannot wait to go again. There is space in the back section of the boat to sit on benches, but me and the ladies spent the majority of our sail sprawled and sunning on the front section .....

Rebecca C. - Yelp Review

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A Fantastic Experience!  We've done a number of the Chicago boat tours, including several of the different architectural tours on large boats with crowds of people.  This was SO MUCH better!  We took my in-laws, who were visiting from out of town, on the 2-hour sunset cruise for six (the maximum allowed by the Coast Guard), and just sailed up and down the lake along the skyline. We loved it!  We lucked out with fantastic weather .....

C P. - Yelp Review

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PRIVATE SAILING CHARTERS
SUNSET SAILS • FIREWORKS • SPECIAL OCCASIONS

708-824-SAIL or Info@ComeSailing.us
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