Our Story

10 years since we launched Free Spirit Yacht Cruises. Hard to believe.

Our story after 10 years.

It’s been ten wild, where-did-they-go? years since Joe and I launched our version of Free Spirit Yacht Cruises.

It started with a pizza (this is a Chicago story after all).

Spinach pizza….all that was left when I ran out to pick one up for a lunch meeting I was having with Joe Donofrio of Free Spirit Yacht Cruises. Little did I know that was the only kind of pizza he didn’t like! I hardly knew him, despite the fact that he’d been trying to get me to come to work with him for a while.

I’d been running my own Chicago-based thirty-boat yacht charter brokerage company, Angela’s Charters, for eleven years. And business was good.

Family-owned Business

Joe worked for his parents, Rich and Judy Borrowdale, in their family-owned business, the original Free Spirit Yacht Cruises, founded in 1983. A captain for eighteen years on their two luxury yachts, Joe is an expert navigator who’s at his happiest when he’s on Lake Michigan.


Rich and Judy Borrowdale

Early in the charter season we met for lunch on the Free Spirit, and while Joe wasn’t too thrilled with the pizza, he was with me. And the feeling was mutual. Short story: in November, 2007, we got married on a beach in Florida, and one month later, we bought Free Spirit Yacht Cruises from Joe’s parents who were retiring.

Today, we’re a thriving second-generation, family-owned private luxury yacht charter company. And we think our skills perfectly complement one another. I manage the business and marketing while Joe keeps our yachts in pristine condition. He crews as well. My daughter, Margaret (who worked with me at Angela’s Charters) now works with us at Free Spirit Yacht Cruises. And Joe’s son and daughter help out when they can. We’re a happily blended, Lake Michigan-loving family.

We also feel very fortunate. Our business launched the same month the recession began (December, 2007) but we’ve been growing steadily ever since. Joe and I love being out on Lake Michigan and never tire of the spectacular Chicago skyline. We look forward to many more happy boating seasons showing guests our beautiful city.

Thanks for reading our story.

Warm regards,
Angela Motolo Donofrio and Captain Joe