Go Sailing Chicago

Chicago, United States

4.9

18 reviews

Contacts

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Telephone:
+1 773-710-7245
Website:
www.gosailingchicago.com
Address:
400 E Monroe St, Chicago, IL, 60603
b/t Harbor Dr & United States Highway 41
The Loop
Nearby public transportation stops & stations:
0.4 miRandolph & Stetson
0.4 miMichigan & Madison
0.4 miMichigan & Monroe
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Good for Kids
Yes

Today

Today –
Local time (Chicago) 12:47 PM Tuesday, June 3, 2025

Business hours

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Description

Specialties

Welcome to Go Sailing Chicago.

Whether you want a romantic sailboat charter for two under the stars, to go sailing along the Chicago skyline with friends, to learn sailing with the friendliest instructors in the city, or enjoy some quality time with family while the sun sets, Go Sailing Chicago has the right Chicago sailboat charter or sailing lesson option for you.

We sail in Chicago from the break of dawn until the deep of the night 7 days a week, so the schedule is always right. We sail only with the top United States Coast Guard Master Captains and US Sailing Certified Instructors the city has to offer, which ensures your safety. And our downtown Chicago location cannot be beat.

Sailing Lessons are all new for 2011. Check out our site, call, or email us for new information.

Sailing and Sailboat Charters, Fireworks Charters, Sunset Charters, Romantic Occasion Charters, Northerly Island Charters, 4th of July Charters, Air and Water Show Charters. Go Sailing Chicago!

History

Established in 2009.

Go Sailing Chicago has quickly become one of the premier, family-​friendly private sailboat charter companies in Chicago. We only hire the most experienced US Coast Guard Master Captains to ensure safety. Of course FUN is priority #1 right next to safety.

Go Sailing Chicago is not just a sailboat charter and lessons company serving the Chicago-​land area, it is an opportunity and your link to any and all things sailing. The mission is to serve the Chicago community well. Now Go Sailing Chicago!

Meet the Business Owner

Michael A.

Business Owner

I went sailing for the first time 11 years ago on a 555 mile trip from Detroit to Chicago. After that trip I wanted to learn everything I could about sailing. In went on to sail the Caribbean, participate in sailboat racing, get my Master Captain’s license, quit my day-​job, and started working as a full time Captain. A few years later I developed the concept for Go Sailing Chicago! and turned my dream into a reality.

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Vicinity

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18 reviews of Go Sailing Chicago

No registration required
Place rating: 5
Valparaiso, IN
My wife and I took an intro 101 to sailing, it was a great experience overall, Capt. Matt did a wonderful job in explaining different parts of the sailboat and how they work together. Very through and helpful. Cant wait to take more lessons.
Place rating: 5
Chicago, IL
I first heard about Go Sailing Chicago through Groupon & booked my first class through that offer. Other than the lack of wind it was a really good experience. I couldn’t get it out of my head and had to sign up for more. I enrolled in Captain Michael’s Intro to Sailing 101 full course (four classes over two weeks) and loved every minute of it (if you ask my family they’ll probably say that’s an understatement.) Kirsten was incredibly helpful with getting me into the class at the last minute and communicating with me throughout the registration process.
Cap’n Michael is an awesome instructor. He found ways to explain techniques in different ways if we didn’t get it the first time, answered any and all questions, and really gave us a true sailing experience. He also sent us study materials after the first class so we could prepare for the next session. After learning from Cap’n Michael I know I can handle myself on a sailboat and can’t wait to get back out there. I know I’ll get the Crew package next summer and am VERY excited! If you’re at all interested in learning how to sail, you should definitely check out Go Sailing Chicago. Go. Do it. You know you want to!
Place rating: 5
Chicago, IL
Booked a trip as a birthday surprise for my aunt. 4 of us sailed on the Mystify with Captain Kirk (yep) it was a blast. Great service from time of my initial request, booking and sailing. We had luck with the weather and it truly could not have been a better experience.
Place rating: 4
Chicago, IL
Captain Tom was excellent. We learned a lot and had a great time. The team at Go Sailing was very accommodating getting me prepared for my lesson. We didn’t have hardly any wind however, so while it was out of their control, it wasn’t the full sailing experience I was hoping for.
Because of the great service, I’m very willing to try it again with Go Sailing, and hope for better weather. Thanks!
Place rating: 5
Chicago, IL
I booked a 3 hour intro to sailing for my Husband’s birthday in July and it was terrific ! Captain Rich was so fun and we learned the basics. We will definitely be booking another trip !
Place rating: 5
Chicago, IL
This review is way overdue!!!
May 29, 2013 my boyfriend celebrated his birthday and we also celebrated our anniversary. I planned a surprise fireworks sail for the evening. I booked early in the season and was able to take advantage of the $ 50 off early booking discount. Go Sailing made my booking smooth and easy with an excellent confirmation system.
The morning of our sail Captain Tom called me to give an update on the weather and to let me know that to expect on the water that evening also to set a plan for the route we might be interested in taking for the evening. The night went off without a hitch. My boyfriend was completely surprised and had an amazing night. We arrived about 30 minutes early and Captain Tom took us out immediately giving us even more time than we booked for which started us off feeling really great about the night. The boat was clean, comfortable and stocked with ice, glasses and an excellent speaker system (which we played the new Justin Timberlake album from most of the sail). Captain Tom even let my boyfriend man the wheel while I snapped pictures.
We ended the evening singing happy birthday and snacking on delicious red velvet cupcakes from Whole Foods (they have a great bakery) and to top it all off the boyfriend had no clue about the fireworks which we enjoyed from the boat. All in all excellent experience and we plan to make it a yearly tradition. Fins was incredibly comfortable for the two of us.
Place rating: 5
Palatine, IL
I hosted a bachelorette party last weekend and as one of the activities, we went for a sail on «FINS» with Captain Tom. It was amazing. Tom was fun, friendly and professional. The speaker system was great, the captain provided the cooler and ice. Really, it couldn’t have gone better. I would without hesitation recommend Go Sailing Chicago!
Place rating: 5
Chicago, IL
Best experience! We sailed with Captain Rich on his boat «Son of a Sailor.» Rich was obviously an experienced sailor and host. He read us well, barely heeled (titled) when he noticed a friend of mine stopped drinking. He’s had this boat for twelve years and you can tell he’s comfortable and knowledgable on the water. His boat was well equipped with ice and beautifully cleaned. He solo sailed our party of six around Lake Michigan and this truly was one of the best boat charters I have had to date! I definitely recommend making sure you have a boat you want to be on and a captain (and possibly crew) that you jive well with. A must summer activity!
Place rating: 4
Chicago, IL
Go sailing Chicago offered a great deal for an intro to sailing class on Gilt City. I wasn’t sure if I’d like it, but I had a blast. I went alone and was grouped w/​one couple and another woman. All four of us were new to sailing so that made the anxiety lessen for me.
Daniel was our guide and he knew his stuff. We went over everything boat related and headed out. He didn’t waste any time getting us out. Everyone worked some part of the boat and we all got to steer which was awesome! The best part was coming back into the city and seeing the skyline against a sunset and at night.
I’d highly recommend Go Sailing Chicago for newbies and experienced sailors alike. I bought a deal but after this, I’d pay full price. Thanks Go Sailing Chicago!
Place rating: 5
Chicago, IL
My family and I had a wonderful experience with the two boats we chartered through Go Sailing Chicago. Both of the sail boats and Captains (Cap’n Rich and Kirk) were perfect. Beautiful day and exactly what we were looking for.
Place rating: 5
Buffalo Grove, IL
I schedule the private sailboat charter for an engagement proposal. Kirsten was EXTREMELY helpful in planning and helping me decide on the boat and time. They were really good about communicating everything I needed to know about prior to the sailing as well including directions, food, drink etc.
We arrived at the harbor and Captain Kirk was ready for us. He explained everything about the trip and we got on board and were quickly off and sailing. He had everything we needed for our food/​drink. Unfortunately we were so caught up in the actual boating and engagement, that we never touched our food/​drink. Despite it being in the low 60s (July 27, 2013), we managed to keep warm and enjoy a nice sunset over the city. Captain Kirk even took the jacket off his back for my Fiancée to wear.
It was a fantastic evening and a memory that will last forever. I would ABSOLUTELY charter another trip with Go Sailing Chicago again.
Place rating: 5
Evanston, IL
We were able to easily schedule, plan and charter the sailboat of our choice for the time we wanted all online and via e-​mail. We arrived, met Captain Ben and had a really relaxing day on the Lake. Ben was highly knowledgeable and very patient in showing us the ropes of sailing (in a casual way, as this was not a lesson, but a pleasure cruise). We asked him lots of questions and he was very patient with us in teaching us whatever we wanted to know. He actually gave each of us a chance to steer the boat while he manned the sails. It was a gorgeous day on the water and we had so much fun. We’d highly recommend Go Sailing Chicago to anyone looking to do something exciting in the city, yet different and memorable.
Place rating: 5
San Francisco, CA
I took the intro sailing lessons and had a great time. The skipper was very knowledgeable and was great at communicating some of the more complicated concepts. Overall a great deal!
The only downside is Go Sailing is not an accredited group so these classes will not count towards a formal US Sailing or ASA certificate…
Place rating: 5
Madison, WI
This was a great experience and I would highly recommend it. Both Mike and Kirsten were extremely friendly and also let us have our space on the front of the boat. Even though we couldn’t really sail (no wind) we still had incredible views of the city, a terrific sunset, and even some fireworks.
Thanks for the great time! A+
Place rating: 5
Chicago, IL
My cousins came in from Vancouver for a wedding. I had gone on a boat tour with them out in B.C. on a previous visit and wanted to show off my city from the lake. I had heard of Go Sailing from a friend of a friend and decided to check it out. I could not have been happier with our experience. We had a beautiful day and the sailing was excellent. It was a perfect way for me and my family to spend some quality time together before the wedding chaos. I highly recommend this unique Chicago experience.
Place rating: 5
Saint Louis, MO
Start to finish, a great experience! Kirsten had the prepwork all done to make things go smoothly from the very first email exchange, and Michael was our captain for the sail… which was magnificent. None of us had been on a sailboat before, and I just don’t see how it could have been better. Thank you both for a great time; we’re really looking forward to another visit!
Place rating: 5
Chicago, IL
My wife and I celebrated our one year anniversary on a beautiful night last week. Michael and Kirsten were very helpful with all of our needs to make the night memorable.
Place rating: 5
Fort Worth, TX
In the course of organizing a 50th bday weekend in Chicago for my brother I wanted to find a reasonably priced way to get out on the lake without being in one of the ‘cattle car’ cruisers or on a 30-​year old Boston Whaler with a complimentary cooler of Schlitz thrown in.
This was the perfect set up for our group of 4, none of us all that seaworthy, I might add. The boat is beautiful, clean and plenty of seating both on deck and below. The two-​person crew was super friendly, engaging and very understanding of our one brother that gets seasick (but did not this time by virtue of their sailing abilities!).
After 3 hours of sightseeing, chattting, and a few beverages, we all agreed that this was the perfect way to get out on Lake Michigan, relax and enjoy views of the city. Thank you!