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Dan Stotesbery 鈥�02 was sailing his new boat a couple hundred miles off the Canary Islands, on the first leg of a 2,500-mile, trans-Atlantic crossing to Grenada, when it hit him: 鈥淵ou鈥檙e really alone. You鈥檙e really on your own to fix things and to make it, and there鈥檚 nobody coming to help you.鈥�

He and his hired crew of four saw only one boat and spotted three others on radar during their 17-day trip. They previously sailed across the Mediterranean Sea from Turkey, where he had picked up the boat he had just bought, to Majorca, Spain, but 鈥淚 didn鈥檛 have that feeling because you鈥檇 always have land around or there鈥檚 always a bailout option somewhere. But there鈥檚 no bailout option in the Atlantic. It was very emotional and psychologically demanding.鈥�

Stotesbery had faith in the boat, a 50-ton, 64-by-17-foot vessel that he had spruced up in Spain, and also in his ability to use modern tools, such as digital weather forecasts and two satellite tracking systems, to make the trip as safe as possible. He texted his wife Kacey frequently. But he already had encountered five days of 鈥渂ig, big seas and big winds鈥� between Gibraltar and the Canaries.

Said Stotesbery: 鈥淲hen you come up on deck, and you see the wind driving the water off the top of the waves, and they鈥檙e towering on top of you, and then you go up one side and you鈥檙e looking down into this huge crevasse, it鈥檚 absolutely terrifying.鈥�

His biggest worry was that Kacey and their two sons, now 9 and 7, would always wonder what happened if he failed to arrive safely. That made him question: 鈥淒id we make the right decision to do this?鈥�

Let鈥檚 rewind. Earlier in life, Stotesbery already had had adventures of a different sort. He traded commodities at the Chicago Board of Trade, before digital trading displaced the pit鈥檚 pandemonium. After the board shut down for the day in the early afternoon, he taught sailing on Lake Michigan. Then, when his father asked him to handle national sales for the family business, Ladera Vineyards in St. Helena, California, Stotesbery traveled the country 300 days a year.

After Kacey became pregnant, Stotesbery stepped away from the sales job, concerned that so much travel would mean 鈥淚鈥檒l never know my kids.鈥� In 2016 his family of four moved to Colorado, where he took over as chief executive officer of another family business that made plastic containers. And then COVID-19 hit, and everybody was frantically searching for hand sanitizer, which, of course, comes in plastic bottles.

鈥淲e suddenly got approached by a big business to buy us out because they needed more machine time and more capacity,鈥� Stotesbery said. 鈥淲e thought it was probably a good idea to sell, a good deal, and so I came to a transition point in my life, essentially firing myself.鈥�

With the pandemic-induced lockdown, Stotesbery had time to contemplate his next step. 鈥淚 thought back about everything, just about my whole life and where I was the happiest, and I was always the happiest on the water,鈥� he said.

He and Kacey mulled the idea of moving onto a boat and sailing indefinitely. They hired consultants to help them 鈥渄ecide if it鈥檚 the right thing for you, help you go through the transition.鈥� The decision made, they sold their house and all their belongings. And they bought the 鈥淧olar Bear,鈥� which they renamed 鈥淗indsight.鈥�

Kacey and the boys climbed aboard early last year, shortly after Stotesbery arrived in Grenada, and the family 鈥� along with a rotating volunteer crew of friends and relatives 鈥� headed north to Portland, Maine, then south again, when Stotesbery crossed 10,000 nautical miles in a year. Since then, 鈥渋t鈥檚 been a lot of sailing and a lot of moving around,鈥� in ports on the U.S. east coast, the Bahamas and Caribbean Islands, where they recently spent the winter months. Then they headed north again, required by insurance to be north of Cape Hatteras before hurricane season started.

Though the family has had amazing experiences, 鈥渋t鈥檚 a lot more work than people think it is,鈥� Stotesbery said. 鈥淭he boat needs constant maintenance and you always have to be trying to keep ahead of that. My wife put it best: Imagine taking your house and putting it through an earthquake every week and seeing what breaks.鈥�

Though he and Kacey have discussed circumnavigating the globe, that dream poses risks, such as pirates, that they鈥檙e not willing to take. They also have postponed a planned but expensive trip to the Mediterranean, as they consider whether the nomad life is right for their children, whom they鈥檝e been homeschooling.

They鈥檝e become worried that the boys aren鈥檛 exposed to enough other children, so they鈥檙e considering docking near other families throughout the summer 鈥渟o that they can have a little more socialization.鈥� They鈥檙e also considering ending the adventure because, as much as he and Kacey love it, 鈥渋t's becoming more clear that (the boys鈥�) needs are a little different from our wants.鈥�

Stotesbery has been asked if he is crazy. 鈥淪ome people would say that,鈥� he said. 鈥淚 mean, it鈥檚 definitely a different lifestyle. 鈥� You鈥檙e constantly changing. And a lot of people are change-averse. They like to have their routine and there鈥檚 no routine on a boat and moving around. But I like change, and my wife likes change. And I think it鈥檚 good to teach the kids to be able to adapt and change and see new stuff all the time.鈥澛�