In the early 1980’s Captains Rich & Judy Borrowdale pioneered the business of Chicago Yacht cruises by establishing Free Spirit Yacht Cruises located in Chicago’s Burnham Harbor. Unfortunately, the harsh winters of Chicago prevented us from enjoying our passion year round. Rather than give up what we loved most for half of the year, we decided to expand our business to Marco Island in Southwestern Florida, during the brutal winter months in Chicago.

We were able to provide this chance of a lifetime to individuals in both Chicago and Florida, and continue doing what we love most, all year long. This innovative opportunity, along with our exemplary service has allowed us to maintain our status as the best provider of Chicago cruises as well as cruises in Florida!

In 1993, our hearts were overjoyed, when our son Joe decided to become a part of the Chicago family business. His expertise furthered our expansion into the business of Chicago cruises. We are also proud to have Captain Joe Donofrio as a member of our Chicago cruise team. He is an expert navigator on both yachts, the “Free Spirit” and the “Gypsy Spirit”.

Captains Rich & Judy Borrowdale have decided to enjoy the warm weather and the beauty of Marco Island year round. Captain Joe and Angela Donofrio are keeping the family owned and operated business alive. Free Spirit Yacht Cruises provides you with luxurious yachts, exceptional service and an event you will want to repeat at least once every year. 

Throughout the years, we have also developed relationships with some of the finest caterers in Chicago. This allows us to provide our Chicago clients with a wide array of menu options for their cruises. More importantly, we are able to offer the most delectable cuisine available in the Chicago area. This amenity coupled with our service and the grandness of our vessels will ensure your event is a success.

From your annual company outing to weddings and everything in between, the occasion is sure to be a glorious success on one of our Chicago cruises. As our yacht charter business continues to flourish each season, we are pleased to welcome many new clients, as well as the return of old friends. Please join our family for an event that will exceed your every expectation!!!