SloopCity Sailing

Chicago, United States

5

Open now

8 reviews

Accepts Credit Cards

Contacts

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Telephone:
+1 312-401-8278
Website:
www.sloopcitysailing.com
Address:
400 E Randolph St, Chicago, IL, 60601
at Field Blvd
The Loop
Nearby public transportation stops & stations:
0.3 miRandolph & Stetson
0.4 miMillennium Station
0.4 miMichigan & Randolph
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Bussiness info

Accepts Credit Cards
Yes
Good for Kids
Yes

Today

Today 8:00 am – 11:00 pm
Open now
Local time (Chicago) 13:06 Tuesday, 24 June 2025

Business hours

Monday 8:00 am – 11:00 pm
Tuesday 8:00 am – 11:00 pm
Wednesday 8:00 am – 11:00 pm
Thursday 8:00 am – 11:00 pm
Friday 8:00 am – 11:00 pm
Saturday 8:00 am – 11:00 pm
Sunday 8:00 am – 11:00 pm

Description

Specialties

SloopCity Sailing provides the finest sailing instruction, and the best Sailboat Charters in the City. We offer basic and intermediate sailing classes, private sailing lessons, as well as private charters for up to 6 people. Join us for a beautiful sunset cruise, fireworks charter, or just an afternoon sail.

Check out our web site and see what we have to offer. We offer excellent instruction at reasonable prices, and charters that can’t be beat. We make it FUN!

History

Established in 2009.

SloopCity Sailing was formed to provide the best, most professional sailing instruction in the city. We have worked hard to continually improve our services, programs, and boats to assure our customers are engaged and satisfied. We offer basic, intermediate, and private instruction on our boat or yours, as well as our popular «Introduction to Sailing» classes.

We now also offer great private charters for up to 6 people on our beautiful Catalina 34. Morning sails, sunset cruises, fireworks sails — we do it all!

Quality charters and instruction at reasonable prices. We make it fun!

Meet the Business Owner

Bob W.

Business Owner

USCG Master Captain

US Sailing Certified Keelboat Instructor

Over 30 years of Experience

Sailing has been Bob’s life long passion. He has been sailing for over 30 years, racing for over 20, and teaching adult sailing classes for 15. He has the experience, knowledge and patience to provide you with a safe and enjoyable on-​the-​water learning environment. SloopCity Sailing offers two levels of sailing classes as well as private instruction. We also offer captained charters for those of you who just want to relax, go for a sail and enjoy Chicago’s lakefront and our fabulous skyline.

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8 reviews of SloopCity Sailing

No registration required
Place rating: 5
Chicago, IL
This is my first post ever on Unilocal,but i felt that BOB deserves credit for all what he did. He is amazing. its the least thing i can do to thank him or pay him back for all what he fought me.
I spoke with Captain Bob for one hour before signing up for the class. He was very patient, willing to answer every question i had and very friendly. Went to the class i felt more of being with a close friend, he has been sailing for a long time, very experienced. He’s not like all the other companies. It’s his passion he loves sailing and wants to share his knowledge and experience to all his students. He doesnt do it for the money, he does it be causes he loves doing it. He gives his class over 4 days so you get to absorb all the information given and experience multiple weather conditions. my 4th day the weather wasn’t that great, he decided to give me a 5th class just to go in stronger wind conditions. Class is so fun you don’t feel you are in class, its so much fun that sometimes it can be even longer than the normal hours. After my course was done i realised i was ready to captain my own boat. he helped me find a boat to sail on. We are always in touch for any further questions i have or even sharing my experience with him. Great guy, amazing sailor, best instructor. would recommend him to anyone that wants to learn how to sail or refine his sailing skills
Thank you very much Captain bob. Wouldn’t have been here without you.
Place rating: 5
Frisco, TX
My wife and I stumbled upon this business while trying to find a sail boat to charter. We are so glad we did. Bob was the only one of 3 businesses contacted to respond to our inquiry and he did so promptly. We were able to sail within 36 hours, just the 2 of us and our captain. Very reasonably priced. Bob has over 20 years of sailing experience, he’s personable, unobtrusive, and very accommodating. I recommend him highly and would use this company again without hesitation. Don’t forget your sunscreen!
Place rating: 5
Centreville, VA
I was referred to Bob by another company for sailing lessons and I’m happy that they did so. I was new to sailing, but Bob made sure I was comfortable with the whole process. I think the most important part of learning anything is having an instructor who is patient and also understanding. Bob was definitely both of those things. If you ever wanted to learn to sail and don’t know where to begin, I would say Sloop City Sailing is a good place to start. I went from not knowing really how to sail to know Captaining my own boat!
Thanks again Sloop City!
Place rating: 5
Upper East Side, Manhattan, NY
My family and I recently chartered a sailboat (the Catalina 34) with Sloop City Sailing and had a blast! It was a surprise Father’s Day gift for my dad who sailed a bunch in his younger days but hadn’t been on a boat in over 15 years. I researched a variety of charter options over the course of a few weeks and am really glad I chose Sloop City Sailing. The boat was very comfortable and accomodating for our group of six and Captain Bob was great company as he navigated us around the lake, taking in the view of the Chicago skyline. I really couldn’t have asked for anything more in a charter experience. Captain Bob is very professional, generous with his time, and offers competitive pricing against other companies in the area. I would definitely recommend Sloop City Sailing!
Place rating: 5
Palatine, IL
Recently enjoyed a 4 hour cruise with Captain Bob on August 22. The boat was awesome, easily fit our group of 4, and Bob is a very relaxed, great captain. We all felt extremely comfortable as first time sailors. Dusable Harbor could not be easier to get to, and meeting up on the dock was very simple.
I can’t imagine a better way to spend a sunny afternoon in Chicago than sailing on Lake Michigan, the views are amazing, jumping in Lake Michigan for a swim is awesome, the whole relaxed, customer’s choice cruise that Bob provided was just perfect. I literally cannot wait to do it again, too bad summer ever has to end. I did a lot of research prior to booking Sloop City, I can easily say I made the best choice.
Place rating: 5
Chicago, IL
Okay I decided to write this review for Bob’s sailing school after our first solo voyage to see if my wife and I were ready. We were and we credit Bob and Sloop City with an outstanding job teaching two neophytes the basics. Literally stepped off the boat an hour ago.
To set expectations, don’t expect anything fancy. You’ll learn on a 25-​foot boat that I’m pretty sure wasn’t the 2014 model. What you can expect, however, is world-​class instruction from a guy who is super passionate about sailing and committed to ensuring you are ready on Day 1 once you venture out on your own.
Would highly recommend Bob to anyone looking to learn the basics and beyond. My wife and I will be going back to him at the end of the summer to get further instruction to charter our own boats next time we are in the Caribbean and other cool destinations. (Don’t worry, Bob, we’ll have at a few months under our belts before that happens! :)
Place rating: 5
Chicago, IL
I can’t say enough good stuff about Sloop City Sailing. I signed up to take some sailing lessons not expecting much after a average experience last summer with 3rd coast, but was blown away by what a great time I had. The lessons were a lot of fun, and while I was taking them it was the highlight to my week, every week. Captain Bob teaches the information in a hands on way so that you are applying what you learn instantly and retaining the information which is really important. As a result of these classes I have found a new passion in life and have one more thing making me wish spring started tomorrow. I have hired guides and taken classes (ie rock climbing, flyfishing, scuba diving, etc.) in six states on on four continents and can say without hesitation that this has been the best money I have ever spent.
Good Job Captin BOB!
Place rating: 5
Chicago, IL
This was the best part of my summer. Bob’s class was fun and educational. I did a lot of research before I ended up booking my lessons with Bob and SloopCity by far is the best bang for your buck. SloopCity changed my mind on what boat to buy. I will be purchasing a sailboat next year. Thanks Bob