Local Legend: A Great Lakes Sailing Journey - Sailed From Lake Michigan to Florida | Teddy Annoye

Have you ever been sitting at your desk job and thought about quitting on a whim to sail from Lake Michigan to Florida. Well, my buddy Teddy did just that. Since you didn't, you can read about his epic journey below. Teddy's experience is proof that water connects us, adventure changes us, and the outdoors brings us home. This legendary trip undoubtably makes him a legend. 

1. You spent 80 days sailing from Wisconsin to Florida — what made you say yes to that journey, and what were you hoping to find out there?

I got a call from a couple I’d met back in high school while working at a marina. We’d kept in touch over the years, and they told me they were about to sail their 63-foot boat down to Florida. As soon as I heard, I knew it was the kind of journey you don’t come across twice—and I let them know I was interested. They told me I had 48 hours to decide.

I had a good job at the time, but there was a big conflict: my brother’s wedding was set for the same stretch of time. I called him to talk it through, and without hesitation, he said, “I can't ask you to give up the most amazing adventure of your life, just to spend one day with me.” That gave me the clarity I needed.

I wasn’t chasing anything specific—I knew it was a once in a lifetime opportunity, and I couldn't miss it. I wanted to live a story worth telling.

2. What do most people not realize about the Great Lakes that you learned during your expedition?

Growing up, I always heard that Detroit was rough—dirty, dangerous, and not somewhere you’d ever want to visit. But on this trip, I found out how wrong that was.

We were looking for a place to rest for the night in Detroit and sent out many radio calls to see if we could find a place to have us. Only one place responded. Not only were they the only ones to respond back to us, but they went above and beyond any expectation we had. We were invited in by a marina in Detroit that was founded by Black boaters who had been turned away from other, predominantly white marinas.  They welcomed us with open arms, generously gave us a spot for the night, filled up our boat and our bellies, and gifted us some souvenirs to remember the stop. It was such a fun atmosphere and we were given a tour and the history behind the place. Out of the entire journey, that marina had the kindest, most joyful people we met. It completely changed the way I saw Detroit. Turns out, what I’d always been told was wrong.

3.  Was there anything you noticed throughout the Great Lakes that was consistent?

Everywhere we went, the people felt familiar. Whether it was a marina in Michigan or a port in Catskill, New York, there was this shared energy. Folks weren’t on the water to make money or be in a huge hurry. They were there to hang out, grill food, and spend time with the people they love. That feeling of gathering around water just for the joy of it — that’s what connects this whole region.

4. What do you think it is about water that brings people together?

There’s a kind of honesty to it. On the water, there’s no room for ego. You meet people from totally different backgrounds — graffiti artists on broken-down boats, marina workers, families, and interesting individuals.  Everyone's sharing space, stories, and food. People aren't bonded by politics, religion, or sports teams. They're bonded by the fact that they all feel most at home on the water. I think it's rare to find something that brings people together so naturally.

This is tenfold when you're part of a crew. When you share meals, confined spaces, and extended periods of time with others you develop a very intimate and understanding relationship with one another. You learn how to work well with each other like teammates. 

5. Looking back now, what did those 80 days on the water teach you — about yourself, and about how you want to live?

It taught me that the most powerful way to stand out in this world is to be completely yourself. You can’t fake your way through 15-foot waves or sleepless nights at sea. Out there, everything is stripped away — your job title, your background, your expectations — and what’s left is just you.
I learned that I don’t need much to feel alive: good people, a little adventure, and natural beauty all around me. That’s more than enough. Anytime I feel overwhelmed by life, I know I can always reset by getting back into nature. I love to sit on the beach, looking at Lake Michigan with the sun on my skin, knowing that everything is all right. 

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