For many of us, the open water represents freedom, adventure, and endless possibilities. For Captain Craig, it’s more than that—it’s a way of life deeply tied to his family, his heritage, and a passion for storytelling.

Having built a career as a professional Captain in Chicago and Florida, Craig has carved out a unique path that blends a love for the water with the excitement of meeting people from all walks of life. Here’s his story, told in his own words.

How It All Started

"I’ve been boating for about four years now, and I attended Maritime Professional Training in Ft. Lauderdale, Florida, to earn my 100-ton Captain’s License. I Captain in Chicago from May through October and Marco Island, Florida, from the end of December through April, with occasional trips to Miami, Ft. Lauderdale, and Naples, Florida.

My grandfather grew up in Greece and was always on the water, serving in the Greek Merchant Marines. I grew up in Chicago, and he lived upstairs from me and my family. He would fish from the shores of Lake Michigan almost every single day, and I often visited him while he was fishing. My love for boating began thanks to an old friend I’ve known for over 30 years, who invited me out on one of his boats about six years ago."

The Fun and Freedom of Being a Captain

"I love the mystery and the freedom of being a Captain. You never know who’s going to show up for your charter. You get one name for the booking, but most of the time, you know nothing about that person or their guests. From MLB All-Stars to NFL quarterbacks, country music stars to reality TV stars, every day is different.

I’ve shot three music videos in three different languages. I’ve had business owners who now feel like family, chartering with me in Florida and Chicago on multiple occasions. I’ll get a bachelorette party followed by a pastor and his family — all on a 12-hour Saturday. I tell everyone it’s the best job in the world. The freedom to take days off when needed, avoid the typical 9-to-5 grind, and the good pay all make this lifestyle worth it."



A Million Stories to Tell

"Every day is an adventure, and I get to work with some amazing deckhands who have become some of my best friends. One of my most memorable experiences was my first-ever charter as a Captain. One of the customers told me she was from the same small island in Greece where my grandfather was born and raised. He passed away many years ago, but in that moment, I knew he was watching over me, and I felt confident I had made the right choice in pursuing this profession."


Captain Craig reminds us that life on the water isn’t just about the journey—it’s about the connections made along the way. Whether hosting celebrities, families, or unforgettable characters, each charter is a new chapter in an ever-growing storybook.