Learn how to sail on beautiful Lake Michigan with Two Brothers Sailing Adventures in Chicago. Our experienced and licensed captains love to share their passion of sailing with everyone. If you are looking for sailing lessons and whether you are a beginner or a seasoned sailor looking for a challenge, Two Brothers Sailing Adventures is the right place for you to learn how to sail in Chicago and on Lake Michigan.

We offer private sailing lessons so you can receive specialized, one-on-one attention with an instructor. Or if you prefer, we can set up group sailing lessons for you and your family, friends or colleagues.

Our captains have been sailing for many years, and are all USCG licensed. All of our ships are annually inspected and certified by the Coast Guard to ensure your safety and comfort.

Meet the crew!

Captain Jeff Harris  |  USCG Licensed Captain

Sailing with a captain that loves to sail and explore everything the Chicago lakefront has to offer truly increases the overall sailing experience. Captain Jeff’s grandfather taught him how to sail when he was just a kid. Born with gills, his love of water transcends to all his sailboat guests and crew!


“Let’s go sailing today! Contact me at anytime to schedule your sailboat experience. We welcome first timers or those with experienced sea legs. The summer on the lake is an amazing experience.” — Captain Jeff

Captain Lynda Stephens  |  USCG Licensed Captain

Captain Lynda’s sailing journey began in the East Atlantic seas. Her father taught her the ins and outs of navigating the ocean, and has been sailing every since. Eventually she made her way to the west coast where she sailed the Los Angeles Harbor areas. She’s an avid world sailor heading up recent charters in British Virgin Islands, South of France and San Diego.

Now here on the coast of Lake Michigan, Captain Lynda brings true flare to our themed sailing adventures, sharing her passion with all those aboard.