Captain Jeff is a really great guy so that makes sailing on his Sea Gypsy really relaxing and fun. The boat is well equipped clean and a pleasure to sail on. I highly recommend Two Brothers to couples and groups alike!

Had such an AMAZING sailing trip w/my peeps – thank you, Captain!!!!!… Highlight of the summer.

We had a really great time during our August sailing. Thank you Captain!

Captain Jeff really knows his stuff. I enjoyed taking sailing lessons with him because he’s knowledgeable and has a great sense of humor. The weather was perfect and the experience was like no other. Seriously, I had a great time and would recommend Two Brothers to anyone!

“Best Sailing Charter In Chicago”  | This company is truly a hidden gem! We will definitely be using them for all of our chartering needs! This was a very clean, nice size boat with an excellent Captain. Captain Jeff is extremely knowledgeable and experienced with sailing and it really shows. He was eager to take us out for a 3 hour cruise and explained all of the cool details about sailing along the way. I love that he allows you to bring any food and drinks and even allowed us to go for a swim while out on the lake. To make things even better, it very reasonably priced, and it is also at a great location with tons of parking! If you live in Chicago like we do, or are just passing through, make sure you take a sail with Two Brother’s at least once! Trust me, you’ll have the time of your life!

“Sunset Cruise” | My nieces and I thoroughly enjoyed our sunset cruise with Jeff. He was very accommodating and courteous. He went out of his way to ensure we had a great, relaxing night. As the other reviewer said, it was a wonderful way to see the skyline in a more private setting on a beautiful sail boat. We hope we get the chance to sail with him again.

“Wow, What a great way to see Chicago… Thanks Jeff” | My family and I had a wonderful time with Jeff and the Sea Gypsy. Jeff was a great Captain. My kids loved driving the boat. It was so nice to not hear a motor running. The view of the skyline was awesome! Do not get to see the beauty of the city from that angle very often.   Thanks Jeff. We’ll be back.