“I got into sailing because I looked out the window one day back in Chicago and I got the itch,” Andrew Earley told us as we got undersail in New York Harbor. “I rode my bike down to the marina, and the first person I saw I asked, ‘How can I get on a boat?’ I helped him with some bags, we went sailing and the rest is, well, history. I ruined my Nikes that day, but it was the start of something really big for me.”

For Andrew, who’s now based in New York City, this little day-sail was the beginning of a new life-changing passion that would take him from his hometown of Chicago across the Atlantic, and eventually all over the world. “After that first day I started doing beer-can racing, and then started doing Midwest Open Racing Fleet events,” Andrew told us. ”In time I started sailing much larger distances, out to Mackinac Island and around Lake Michigan, and then I made my way to England, and started working toward my RYA Yachtmaster license.”

The RYA Yachtmaster, a designation given by the Royal Yachting Association of the United Kingdom, is the international equivalent of a U.S. Coast Guard Captain's License—not something easily acquired. Andrew's approach to sailing is akin to someone cooking, liking it, and then shipping off for Le Cordon Bleu (or, in his case, the United Kingdom Sailing Academy). “I think the all-in for me is that sailing somehow blurs all of the things that I’m passionate about,” Andrew told us. “There’s the sailing, sure, but a good sailor is also a good cook, makes a mean drink, has got to be social—especially if you’re going to have crew on board—and who doesn’t mind a little adventure and travel? I think that was the biggest draw. You start to meet other sailors and hear their stories. It seems almost like a fantasy at first, but then you realize that you can do it, too. Then you have stories of your own, and you end up in this special place—you reflect, almost like, ‘Oh man, I did that.’ That’s kind of where I am today.”

And it’s not just recreational sailing for Andrew. When he’s not working his day job at a global marketing firm based in New York City, he’s working as a captain for the Sailing Collective, a bespoke charter company that has taken him all over the world. “I’m a bit biased toward sailing locations, and have to say that I’m still a big fan of sailing back home in Chicago,” Andrew told us as we sat back at New York’s North Cove Marina after a day on the water. “Sailing in Chicago is all about the coastline, where you start and where you finish and what you see and do along the way. Sailing in New York involves a lot more tacking back and forth. But getting offshore and sailing in Europe is hard to beat. I’m a big fan of the Costa Brava in Spain, great cruising. But, that being said, I keep coming home to Chicago.”

“Sailing has definitely shaped my life off the water as well,” Andrew told us. “When you think about what it takes to be a captain on a ship—responsibility to yourself, the boat, the crew, prioritizing things—it’s not that much different than working in a corporate setting. I feel like sailing has really given me a strong skill set that I can transition between land and sea, which is nice. There aren’t many things that I apply to my desk job that I don’t use every time I going sailing.”

Whether he’s sailing back in Chicago, in his new homeport of New York, or in some far-flung exotic destination, for Andrew, it’s all about getting out on the water and embracing the community he’s found there. “One of my favorite things to do is help other people tie-up at the dock when they’re coming in off the water, because you never know what kind of trip they’ve had, where they’ve been or what they’ve experienced, but you know that they could use a hand,” Andrew told us. “That’s one of those feel good moments for me, it brings you back to the true mariner’s culture, and that’s what it’s all about.”