Cap’n Michael went sailing for the first time 12 years ago on a 555 mile trip from Detroit to Chicago. After that trip he wanted to learn everything he could about boats and sailing. He soon went on to sail the Caribbean, participate in sailboat regatta racing, get his Master Captain’s license, quit his day-job, and started working as a dedicated full time Captain. A few years later he developed the concept for Go Sailing Chicago and turned his dream into a reality. 


For Cap’n Michael, Go Sailing Chicago is not just a sailboat charter company serving the Chicago-land area, it is an opportunity and your link to any and all things sailing. It’s his vision to serve the Chicago community well. If by the time you are done looking through this site and don’t find what you want, we will refer you to another site or company just to help out!


Cap’n Michael absolutely loves sailing and he wants to share that love and passion with you.  The Cap’n says, “get out there and Go Sailing Chicago!”

 

Meet the Owners and Captains


Here at Go Sailing Chicago, we want you to know who you are sailing with. Take a look at our bios and get to know us a little. The Captains are the driving force of Go Sailing Chicago with each and every one of us as committed as the next to providing the best sailing experience Chicago has to offer. 


All of our Captains hold a current US Coast Guard Master Captain’s license, a fact we take deep pride in. Combined, we have over 100 years of sailing experience. We are all current in First Aid and CPR training. 


Safety is our #1 priority right next to fun. Now let’s Go Sailing Chicago!

Home       Sailboat Charters       Sailing Lessons       Rates       Faqs      Our Boats      Locations      Contact      About Us  

  

Not only do we work with the Captains listed above, but we also recruit other Captains to fill in when needed.  All of our Captains meet the highest standards whether as full time, part time, or freelance.  The staff at Go Sailing Chicago says have fun and Go Sailing Chicago!

Cap’n Michael

K - “The Admiral”

Meet K, the Admiral of Go Sailing Chicago.  Kirsten, or K as she likes to be called, is not only the Admiral but also one of the owners of Go Sailing Chicago.  K was introduced to boating as a child on the west coast taking trips out to Catalina Island off the coast of California.  A few years ago she was formally introduced to sailing and never looked back.  Not only is K an owner but you will find her out on the water on many of the charters.  She believes in a hands-on approach to ensuring a great experience for each and every customer.  K is involved in all aspects of operations and is the main contact person for all of your sailing needs.   She will answer your calls, email, and texts. 

The Admiral says, “Go Sailing Chicago!”

Cap’n Ben

GoSailingChicago.com

Interested in working for Go Sailing Chicago? We are always looking for the best talent the city has to offer and even offer opportunities for volunteers.  Contact us today to see if you have what it takes.   773.710.7245 (SAIL)

Cap’n Ben’s was first introduced to sailing in the mid 1960’s as a child in Long Beach California sailing an 8ft Dutch Sabot Pram.  It wasn’t until Ben started racing offshore in Chicago in the mid 90’s that his passion for sailing really kicked in.  Cap’n Ben has sailed 13 Chicago to Mackinac races, raced in the Key West Race week, numerous port to port races, Chicago NOOD regattas as well as 5 Double Handed long distance races winning two!  Ben has sailed across the Atlantic Ocean, enjoyed the warm waters of the Caribbean, Southern California and Chesapeake Bay.  Ben’s love of sailing extends to being a US Sailing Certified Yacht Measurer and Sailing Instructor.  Cap’n Ben is a Master Captain and Sailing Instructor and says, “Let’s Go Sailing Chicago!”

Cap'n Kirk began his competitive sailing career at the age of 11 on the lakes of Northern Wisconsin.  Over the next 30 years, Cap'n Kirk carried his love of small craft sailing to the University of Wisconsin and then to Chicago.  In 2005, Cap'n Kirk began club racing and teaching sailing.  As an active member of US Sailing and the MORF racing club, lake crossings are a regular event for Cap'n Kirk, who has a particular interest in port-to-port overnight races and cruises.  Learning and studying modern sailing history, storm tactics, engineering, and all things weather related are passions for Cap'n Kirk, and he looks forward to sharing these interests with students and crew alike.  Cap'n Kirk is a Master Captain and Sailing Instructor and wants you to Go Sailing Chicago!

Cap’n Kirk

Cap’n Matt

Cap’n Matt got hooked on sailing at a young age sailing small boats and windsurfing in Chicago and on the East Coast.  His love of sailing has taken him to many coasts to sail and windsurf, but Lake Michigan has been his homeport over the last 12 years. He enjoys taking friends and friends-to-be out on the water to show them the ropes or to let them relax and enjoy the water and scenery Chicago has to offer Cap’n Matt is the sole Captain for Obsession.  He understands the meaning of service at the highest level and as such, he is our luxury Captain. Cap’n Matt is a Master Captain with Go Sailing Chicago and he wants you to Go Sailing Chicago!  

Steph - First Class Mate

Prior to 2005, Cap’n Steph had dreamed about learning how to sail after many days of looking out on the lake.  After watching the Chicago Air & Water Show from a sailboat she put a plan into action.  Through taking lessons, racing on 420’s, acing her US. Coast Guard exams, and now owning a sailboat with her husband, she has become a First Class Mate.  Her experience of 1,000's of sea miles, thoughtfulness, and professionalism will help make your sailing experience a fun and relaxing event to remember.  Steph works on Obsession and will ensure your luxury experience.  She’s looking forward to welcoming you aboard and showing guests how to enjoy the warm breezes & smooth seas that she now cherishes.  Steph says, “Let's Go Sailing Chicago!”

Book by April 1 and receive $50 Off!  Use promotion code 4113 at checkout.

Cap’n Rich

Captain Rich grew up sailing the waters of Long Island Sound.  His love of the water led him to the U.S. Coast Guard Academy where he graduated with a B.S. in Ocean Engineering.  Rich served for five years as a shipboard officer in the Coast Guard.  Rich worked in the corporate world for more than 20 years before leaving that behind for his current role as a middle school math teacher and coach. Rich is a licensed Master Captain and also a U.S. Sailing Certified Instructor.  He owns his own boat and many miles have passed beneath his keel.  Rich has sailed extensively on the Great Lakes and has sailed in the Caribbean.  The only thing Rich loves more than sailing is taking others sailing with him and showing them a great time!