Their first boat was a Catalina 22, which Alison and Chris Major of Zeeland, Michigan, bought when their two children were toddlers. They had no previous boating experience, but they had a desire to learn. “Everything that could go wrong went wrong, but we had the right attitude. It was a good adventure,” says Alison. So good, in fact, that they eventually traded up to a Catalina 30, on which they made longer trips, running north to places like Mackinac Island.
During the Michigan winters, Alison would continue her sailing education on YouTube, where she was exposed to the idea of a dream cruise. “People were sailing around the world, but I knew we weren’t ready for that. Then I saw the canals in France and wondered if there was something like that in North America.”
Eventually, she discovered the Great Loop. “That got my wheels spinning,” she says. “So, I started working on Chris. It took a little time to get him on board, but once we were committed, we were intentional about our plan.”
Their goal was to run 5,200 nautical miles of the Loop while working and homeschooling their children, Ewan (10 at the time) and Gwynnie (8). The couple wanted a bigger boat for this trip—three staterooms would be key. They found a 2005 43-foot Beneteau Oceanis 423 in Virginia that was just right. They moved aboard right after they bought it, and began their adventure out of Norfolk in spring 2023. Fifteen months later, the Major family finished the Loop and then decided to keep cruising for another nine months. They returned home two years later with more than 7,000 nautical miles in their wake.
Like any boat trip, this one went to plan, until it didn’t. “Things didn’t always work out, and that stuff made for great stories,” says Alison. “We had to embrace a certain amount of uncertainty, but that’s boating in a nutshell. If anything, you grow as a person and learn something about yourself.”
The family was always learning on the Loop. And they got great advice from America’s Great Loop Cruisers’ Association, a group that supports and connects boaters before, during and after their travels. Information is shared through online forums, social media and in-person events. “The community is amazing,” says Alison. “They gave us local knowledge in advance of our trip, but we were also looking for these members while we were cruising. Whenever we saw an AGLCA burgee on a boat, we’d anchor nearby to find out where the crew had been and what they had learned.”
Now with one Loop under her own belt, Alison has her own hard-won advice to share. Her book Remote Work Afloat is for those who want to set up an efficient office and thrive professionally while underway. “When we started our trip, the AGLCA was the main source of information, but when it came to working remotely, I had to figure it out on my own,” says Alison, a software engineer who recently transitioned to teaching as an adjunct professor at Lewis University near Chicago. “There wasn’t much out there that was Loop-specific.”
Alison also created a website for boaters, LoopLifeAcademy.com. It’s an interesting mix of educational resources that range from a good blog and travel journal template to paid online courses and even personalized coaching.
“I want to help people embrace a nomadic lifestyle,” she says. “I would love to see more families out there, in large part because the experience was so great for my own family.”
Photo by Chris Major
Jeanne Craig
jeanne.craig@firecrown.com
December 2025
