In 2012, we set out with 2 Duffy boats and a dream of giving Chicagoans and visitors the experience of boating on the Chicago River. Today, we operate 45 boats across 5 locations, but our dream remains the same. We are proud to be the city’s premier local family-owned boat rental operator, and have enjoyed watching the Chicago River transform over the years from a primarily industrial waterway into the vibrant destination that it is today.

Over the years, we’ve welcomed tens of thousands of guests from all 50 states, over 40 countries, and, of course, all across the Chicagoland area. We are so honored to be a part of celebrations, birthdays, marriage proposals, gender reveals, corporate outings, family reunions, date nights, and so much more over the past 15 years. Thank you for boating with us in Chicago!

Ron Silvia, President 

Raised on Cape Cod in a family boatyard, Ron has been a boat lover his entire life. From tagging along with his dad in the yard as a kid, to sailing the coast of Maine as a teen, to earning a captain’s license at just 18, Ron knew from a young age that boating was always going to be a core part of who he was. That passion followed him to Chicago, where he quickly fell in love with boating on the Chicago River and in the Great Lakes. He co-founded the Chicago Boat Company with a mission of giving everyone an opportunity to experience the city from behind the wheel of a boat.

Ron shares his love of the water and boating with his wife and two children. When not on the water, Ron can often be found skiing, traveling with his family, and spending time with friends. He has a bachelor’s degree from Bentley University, an MBA from Loyola University Chicago, and holds a USCG 100 Ton Master license. 

Caroline Winter, Vice President

Caroline has found joy on the water for as long as she can remember — boating, swimming, wakeboarding, and living her best life in a life jacket. Her love of boating became her unexpected career in 2012 when she helped launch what is now the Chicago Boat Company. Proving her stamina and value in those first days, Caroline devoted much of herself to the company's early success and growth. 

When she’s not at work, Caroline can be found enjoying life with her husband and two young children, traveling with family to Northern Michigan or to her husband’s native Brazil, exploring Chicago with friends, and, of course, taking a boat ride or two. Caroline has a bachelor's degree from DePauw University and is a USCG-licensed captain.