We had a great time sailing! It was rough chop out in the Lake so like any good captain, Jeff improvised and brought us back to safe harbor for a cruise in his 1956 speedboat and swimming from the boat. It was the safe thing to do and we still had fun.

You cant beat a summer day in Chicago on the water with Captain Jeff! Jeffs sailing experience paired with his ability to cater towards the different groups of people he brings aboard is amazing. We had so much fun a couple summers ago sailing with him, we rebook with him every year. Jeff is timely, courteous, knowledgeable, and able to sit back and let his customers enjoy their time together. He also allowed us to swim! What an amazing time...we will absolutely be booking with him again. Thanks Jeff!

My wife and I had a great 2 hour cruise downtown and back this morning with Captain Jeff and Max. They were considerate and communicative and wed definitely do it again. In addition to being attentive to our needs, they are stewards of the Lake - Captain Jeff maneuvered off course so that Max could snag a bag out of the water that wasnt even ours! He is serious about conservation and keeping the Lake clean for all. Thanks guys -appreciate you

I just finished a sailing “refresher” lesson with Captain Jeff this morning and I had a fabulous time! Last I sailed with him was in 2019 and I was so glad to sail with him again. After getting my bearings and going over some sailing fundamentals he agreed that we could take the boat further out on Lake Michigan at my request where he let me take the helm and practice tacking the boat (even though it went over time). That surpassed all my expectations. Thanks to Captain Jeff and his first mate, Max for a great day!

Captain Jeff and his sailing adventures are so much fun. There is never a dull moment. I would highly recommend sailing with Two Brothers Sailing. My wife and I love going.

We did a team outing with four boats and four captains-- three of whom were excellent, and one of whom (Captain Jeff) was extremely unprofessional. He made lewd remarks to the two intern girls on his boat, touched them inappropriately (waist, lower back) and made comments about how he wanted to take out one of the girls out on his boat for her 21st birthday on Saturday. Although the other captains were great, we decided not to give any gratuity because of the negative experience with Captain Jeff. Will find another company for our next team outing.

My family and I were extremely excited for our sailing adventure in Chicago while my parents and sister were visiting. Our charter was supposed to start at 1:00pm. My family and I arrived 5 minutes prior to boarding time and had to call Jeff multiple times before getting in touch where he told us to go to a different dock than originally told. There was a group on the boat before us so we did not get on until 1:30pm. There was potential inclement weather coming around 3:00pm since this was an issue because we were supposed to start 30 minutes before that. The boat was not very sanitary and there were multiple bugs/flies in the back. Since there was inclement weather that started around 2:30pm, we headed back in early and Jeff stated we could have a 1-hour credit. We were unable to enjoy 2 full hours and I asked for a refund since we did not enjoy the experience, I was told there could be no refunds. Do not book this experience with a family visiting as it was poor.I was then messaged on Google Reviews to reach out to the owner to fix the issue and they never responded to my email.

My party and I were not as satisfied with our experience as we hoped. First off, it was my moms 60th birthday party. Jeff knew about this and indicated he would do something extra for my mom with either food, drinks, or a fun adventure, but nothing out of the ordinary happened. Luckily, we brought our own food and drinks. Water was not even included. My mom did not receive any special attention, as promised. Additionally, given that we had some older guests in our party, there was no step stool to help assist with them getting on the boat. They had a hard time jumping on the boat. Jeff did not mention previously on how to get on and off the boat, which would have been helpful in making our decision to utilize this company. Furthermore, Jeff was making business phone calls while on our trip, so it made some interruptions. He was also busy with his phone calls that he made a member of our party sail the boat majority of the time, which is not ideal. Last but not least, and probably the worst part of our trip, was that the trip ended a half hour early! We paid good money for our two hour sailing trip, to then only have it last for 1.5 hours. We were very disappointed. Jeff, nonetheless, was a very vibrant personality, so he did make it fun and an interesting experience at times. I just feel overall it could have been more professional and communicated.

Our time with Jeff was amazing. He took us sailing over the lake and we even learned a little about sailing! Great value and time. Definitely recommend Jeff!

Not sure if these are actual reviews. Had planned to lessons but instructor was a no show at a sailing event she posted and hosted and did not attempt to communicate a change of plans or apologize for doing this. I

This sailing experience was above and beyond!! We had SO much fun. Jeff and Linda were the nicest hosts and guides to the experience. From the beginning Jeff was very responsive and attentive he always answered the phone to answer questions and help us book. When we got there, they made us very comfortable and tailored the trip to what we wanted and needed! The boat is also very clean, and new. It was a gorgeous sunset sail and we all ended up jumping in the water haha I was pretty nervous jumping in and they went first to calm me down and help me get in!! I would highly suggest booking with them and no one else I dont know how any other company could compare to this experience we had. Ill never forget our Two Brothers Sailing experience in Chicago. Made our trip very memorable and we will be back to sail with them every time were in Chicago!

Such a fabulous afternoon on Lake Michigan! Captain Jeff was enthusiastic and a great teacher (we did a lesson). I highly recommend this for a unique outing!

Captain Jeff is incredible! He is fun, accommodating, & far exceeded our expectations. He also let us steer the boat & swim in Lake Michigan!! Money very well spent.

Sail Lake Michigan with Chicagos Best Sailor! We had the best time sailing with Captain Jeff yesterday. Not only was he very knowledgeable and a great teacher on the water, he was friendly and a great joke teller! He made our day very special and seeing the sunset from the water was breathtaking. His boat was clean and our time on the water just flew by. He gave us a chance to stop out on the lake and some of us even swam (the water was too cold for me). We were a bit skeptical at first, but he was like sailing with my big brother from another mother! Dont think twice: Book your trip with Captain Jeff!

Our trip with two brothers sailing was by far the highlight of our trip to Chicago. The sailboat was beautiful and well maintained, it exceeded our expectations. My girlfriend and I Initially had requested a three hour sail, but the emerald green water and the sailing of our Capitan Jeff easily had us asking for more time. Jeff was so accommodating and great to talk to. He left us alone to share some great romantic time together and was such an interesting person to have captain the boat. I felt we left not only having one of the best experiences of our lives together but also making such a great friend in Jeff. I searched all of the charter companies listed on TripAdvisor and other sources, two brothers sailing answered all my questions beforehand and made me feel very comfortable with the decision to choose their charter company. Expectations were exceeded. We will definitely be sailing with them again upon returning to Chicago.

Great day sailing with Captain Ken. They were able to fit us in on fairly short notice Father’s Day weekend for really special sail with my son.

Captain Jeff provided an excellent experience!

Jeff and Jimmy were amazing