Chicago Sailboat Charters

it was a nice morning out so we had a really good sail for Labor day weekend! You’ll get to soak in the skyline of Chicago!

Took a nice afternoon sail on Lake Michigan with Captain Rob. He’s very friendly, outgoing and knowledgeable about the lake, the city, sailing and a host of general topics! We had lunch and enjoyed the beautiful skyline and lively conversation! This is a terrific way to experience Chicago and the lake. The boat we chartered was clean, well-​maintained and ready to accommodate your group… we had six adults.
If you are looking for a relaxing and fun way to spend some quality time in Chicago we highly recommend calling Capt. Rob and chartering a sail. Pick up a nice loaf of crusty bread, a nice selection of tasty cheese, sandwiches, some snacks and a couple bottles of wine and head down to the Belmont Harbor marina. You’ll enjoy the experience! Cheers!

Had a great time on the water with Captain Rob! My family (5 people total) booked a Monday morning sail during a recent trip to Chicago which ended up being one of the highlights of the entire trip. The weather was picture perfect and the boat (one of the large class sailboats) was spacious and comfortable, with way more space than we needed. Captain Rob was really friendly and knowledgeable. We were even able to anchor in the playpen to go swimming with amazing city views in the background.

We weren’t even off the boat and my friend and I were already planning our next trip. We booked two of us for a Monday sail on the 31′ sailboat. It was $ 300 for 3 hours, very reasonable and worth every penny. Captain Rick was so friendly and flexible. We’ll definitely request him again! Chicago summers are short so make this top priority on your bucket list!

Captain Conley and Matthew were absolutely awesome. The boat was clean, safe and had plenty of room for our seven people party. The occasion was a celebration and spreading of ashes of my mother and my uncle in Lake Michigan, and this day would’ve been mom’s birthday. Conley was aware of the situation, and very empathetic, which was great. We went out into the lake at least a mile, giving us great views of the beautiful Chicago skyline. Of course we took tons of pictures, and a great time was had by my wife two sisters, uncle and nephew. I will plan a trip with these guys next time in back home in Chicago!

This was such a great experience! Captain Rob was very knowledgeable and did everything he could to make it an enjoyable trip. We were running a little behind schedule, and he called to make sure everything was fine and waited until we got there to head to the boat. The weather was a little cooler than I had hoped, but the views were spectacular. The boat was really roomy and they had lots of stuff (beds, towels, plates, cups, ice, etc.) to make our time aboard more comfortable.

Captain Rob made our evening! He is affable and knowledgable — and was so kind to entertain our request to teach us sailing basics. I hope to book another sail soon and will definitely request Captain Rob!

Planning our trip with Sarah was painless, she so patiently answered all of my questions and made the booking process super easy and comfortable. Especially since this was my first time planning a boat day for a group.
Yesterday our boating experience with Capt. Steve and First Mate Alison was literally the best day ever. Couldn’t have been better.
Our boat was huge and comfortably fit all 10 of us, and was over and above what I expected. We had great fun, awesome weather and such a great group — Alison and Steve were the perfect compliment to our day.
this was such an awesome experience, i rate Chicago Sail Boat Charters and their Crew an A+++!

I bought a Groupon and upgraded tickets on their website as an anniversary surprise for the boy. Weather was absolutely lovely. Perfect for sailing!
There were two other couples on the boat. The ride out to/​into the lake was very enjoyable. However, I began to get nauseous. I wasn’t the only one because other passengers began to feel the same way. I didn’t want to make a fuss and ruin everyone’s fun, so I held onto the boy, remained quiet and closed my eyes for the rest of the trip back. If you think you get motion sickness easily, don’t make my mistake and go downstairs into the boat. It was like a grown up version of a bounce house. Oy. But if you don’t get sick easily, go on ahead with your bad self! Unload any snacks or drinks you may have since the boat is BYOB.
Overall, the trip was very enjoyable! Absolutely loved seeing the Chicago skyline. Captain was nice and seemed very knowledgeable. I would just suggest perhaps instead of racing to see how far you can get within an hour and a half, float along the lakefront and enjoy being on the lake? A la «it’s not the destination, it’s the journey» kind of feel?

I got to sail a boat. While tipsy. Winning.
I got to hoist the sail. While tipsy. Winning.
I got to sit on the bow of the boat and watch the sunset across the beautiful Chicago skyline. While tipsy. I can’t win any harder.
If you’re looking for an exciting and romantic evening that will rekindle your love for the city with a crew of friendly and professional sailors, this is your spot.
Plenty of parking for only 6 bucks after 6pm that’s a short walk from the dock.

Thank you Capt Larry and Amy for a beautiful boat outing on Lake Michigan. They were so accommodating and incredibly friendly. We had many options for our a.m. Sunday funday… I am only able to remember two. The first being a river tour and the second (we chose this option) was the playpen where we anchored the boat not far from Navy Pier.
Swimming, laughter and great conversation… what a treat to relax and spend time with cool people.

Highly recommend this company. 6 of my friends took a private boat on a brisk Tuesday night. The weather was a little iffy before we left (rain and windy). The captain was very straightforward about the expected conditions while on the lake and gave us the option to reschedule. We were thankful that we took our chances.
The weather ended up being perfect. The private boat was clean. The below deck is equipped with everything that you need, including a jack to plug in your Iphone.
We all had a great time. Our captain was easygoing and very friendly. The entire boat experience lasts 2.5 hours. Can’t wait to be out on the lake again!

Ok I literally cannot believe they have a perfect rating. We booked the sail trip 1300 $ for 13 of us for 3 hours. It’s all byOB, I think for 1300 they should provide at least 2 bottles of wine. We were coming from about an hour and a half away and the weather forecast was horrible so I Called the day before and talked to Pj. He specifically told me he would call me at 12:30 (3 hours before our sail) to let us know if we needed to reschedule or not. Great. My friend was getting a different story so I Called again and got Marty, the owner, I told him what Pj told me and Marty basically called me a liar and told me Pj would never tell anyone that. Then we got on the boat. It barely fit us and we were uncomfortable. The captain Steve had about as much of a personality as my left shoe does. Bad experience. Never ever again.

Went sailing with Chicago Sailboat Charters through a Unilocal Elite event and had Captain Bill and Captain Larry. They were super entertaining and fun, cracking jokes the whole entire time. I liked seeing that they worked so well together, and you could easily see that they love their job– always nice to be in that kind of atmosphere.
We went sailing on Lake Michigan around sunset– and it was absolutely beautiful. The breeze was kind of strong and the waves were bigger than I was expecting for a lake— which made for a good sail, but I definitely would have been seasick if I had been drinking like some of the other people on board (BYOB). It was just nice to enjoy the view of the Chicago skyline and be out on the water. I would definitely recommend Chicago Sailboat Charters to anybody looking to rent a sailboat for some fun times on the lake!
Oh btw it took me like 20 minutes to find this place because I have a horrible Windows phone that doesn’t have the Google Maps app– instead I’m stuck with whatever default Maps app that comes on the Windows phone and it took me forever to find this place. It’s closest to the Addison-​red line stop!

Yea! So much fun! Went out with CSC last Monday night and I had such a great time. I definitely plan to go out again this summer.
Very easy to find, just go south of the parking gate and look for the neon green picnic table. All the staff there made us feel welcome and helped us on board. We happened to be on a 39 foot boat (the name began with a V, I forget what it was) and it was really great. The boat was clean and equipped with a small kitchen/​fridge/​cooler, small bathroom with shower, and a living room type area. The upper deck had a bunch of places to keep your drinks, sunglasses, and everything else.
Captain Steve took great care of us, as did Alison and Tatiana who helped with the sails and drinks. Captain Steve made us all feel safe and answered all of questions about sailing, the meaning of life, etc.
There are definitely many options to choose from with CSC for your Lake Michigan excursion so don’t hesitate to ask, all of the staff were very accomodating to our requests and inquiries.
I would definitely book a trip!

What an amazing evening!
We sailed off onto a somewhat-​chopping (but made it fun!) Lake Michigan in what was «the conditions sailors live for!» our captain said. We popped champagne, wine, beers and for 75 minutes, coasted across the blue Great Lake, watching the sun dip behind the horizon and the city’s skyline sparkle.
People on our charter were asked if they wanted to help out; some did «things’ with ropes, others took the helm, etc etc. There was optimal seating, a bathroom downstairs, plenty of cup holders and more. I’ll DEFINITELY be back to Chicago Sailboat Charters for another go at sailing.

Highlife tallboys… check, Jewel brand chex mix… check, legit boat shoes I get to bust out once a year… check, hoodie because it’s never going to get warm in Chicago and before we know it it’s going to be winter again… check.
Set sail with Chicago Sailboat Charters last night, and I have to say, it was a great way to spend a Monday night. We got on board one of their luxury 39′ sailboats for a 6pm skyline cruise of Lake Michigan. The boat had all the amenities you could ask for. Below deck, there were 2 bedrooms, a small dining area, and a kitchen which featured an ice bin for bottle storage, fridge, cups, coozies, wine openers… basically whatever you needed. Also important for those who are drinking, a bathroom.
We had the priviledge of having Captain Steve as our guide. Honestly, I would probably book another boat tour just to hear more of this dude’s stories. Born in France, moved to Chicago at an early age and took up sailing with his dad, lived in Mexico and owned a parasailing company, plays in a blues band, owns an Escalade limo, and is an ordained minister if you want to get married on the open waters. Forget the Dos Equis guy…
The sail was a great time, and we had some amazing views of the city. I would definitely use this company if you are looking to book a sailboat in Lake Michigan. Everyone there seems very professional and most importantly, flexible, given how weather conditions can change rapidly in Chicago. Also gotta give a shout out to Alison, Captain Steve’s assistant, who was doing work up top managing the sails!

Anytime you combine sailing and drinks, you know you are heading for a good time. And Chicago Sailboat Charters did nothing to disappoint. Everyone from Marty to our Captain Matt and his right hand man Rick were great. Even with some turbulent waters, they made everyone in the boat feel extremely comfortable and answered every question we asked.
We were out on the water for roughly over a hour but the time seemed like it was flying by because we had so much fun. Matt and Rick had control of everything the whole time. Matt shared his stories of past groups and their wild times and Rick took care of anything we needed.
To live in Chicago and not go sailing is almost a travesty. So you decide to charter out a sailboat group, make Chicago Sailboat Charters your first stop. These guys are professional, fun and knowledgeable and go above and beyond to make you feel comfortable.

Chicago Sailboat Charters rocks, and if you get Captain Steve and Alison you are sure to have an awesome time. He is very knowledgeable, friendly and personable, they made it feel as if you were just out for a ride with friends as opposed to being on a charter line. He made you forget all about the 3 foot waves and wind, and we had nothing but confidence in his skills in dealing with these conditions. I can honestly say this has been my best and favorite sailboat experience so far, and I’ve had quite a few.
I will definitely be back to Chicago Sailboat Charters, and I will definitely request Captain Steve and Alison!

Chicago Sailboat Charters has a gem in Captain Steve and Alison, and I’m so glad I was able to meet both of them as well as set sail on his boat.
I truly am going to be organizing a group of friends to go back so they can experience the fun and knowledge of Captain Steve.
I was a little afraid because the water wasn’t that calm when we went out but thankful it started to settle as we got further out and I was able to relax and laugh at the great stories that Captain Steve told us all about.
Alison was always smiling and she was very helpful to us all.
The cost is about 210.00 an hour with a 3 hour minimum plus tax and gratuity and up to 12 people can ride in the sailboat so that can be as little as 60 to 70 dollars a person. You can’t beat that deal!!! You are able to BYOB but no red wines I believe but don’t quote me.
I wouldn’t wear flip flops and dress like I did because you want to be able to walk around and experience the sail boat. I would say shorts or pants and a pair of shoes that aren’t slippery.
If you get a chance go go go and IMO Captain Steve and Alison are the best!
Enjoy!