IN-FOCUS ARTICLE: Kimberly Ward, Writer

Jun 25, 2025 | In Focus Articles

Written by: Scott Bishop

Some trips take you from one place to another. For first-time author Kimberly Ward, the 7,000 nautical mile, two-year trip that she, her husband, and their 10-year-old daughter took from Mattapoisett to Grenada ushered them from their old life into a new, transformed one. Their family formed a Crew of Three, the title of the memoir she’s written about that trip.

But it’s not a standard-issue travel memoir. It’s a document, Ward says, about being willing to “dream boldly, then start your plans” and put them into action.

The path from Massachusetts to Grenada—and the return trip, to that new life back in Mattapoisett—started when Ward met Michael, her future husband, an avid sailor, while they worked together as freelance technical consultants on a project for the University of Pittsburgh. They hit it off, Ward says, but she lived in the DC Metro area, and he was up in Massachusetts. “He’s fun,” she thought, “but geographically undesirable.”

“It’s kind of laughable now,” she says. “We were kind of tiptoeing around dating, trying to figure out where things were going. Then 9/11 hit. He was going to a conference in San Diego, and I was flying out to meet him the weekend after he chartered a boat.

“I spoke to him on the 10th of September. He was on a project at Harvard, and they had an issue, and if he had to go into the city, he was going to miss his flight out that afternoon of the 10th and would have to fly out the morning of the 11th.

“So on the morning of 9/11, our entire world changed, and all that kept playing in my head was, ‘Was he on that plane that just hit the World Trade Center? Or was he on the last one that made it out the day before?”

Fast forward: they dated, got engaged, and Kimberly moved up to Mattapoisett. They married and expected to start “a big chaotic family, and we were only able to have one child [their daughter Ally]. When we finally embraced our little crew of three, my husband and I had done a lot of traveling, and we decided we’d travel [as a family]. We’ve taken two cross-country RV trips, once when my daughter was three and again when she was four, and we camped our way through the National Parks of the country. We did a lot of traveling out to Colorado and Virginia to help out as family [members] aged.”

The seed of their nautical journey was planted by sailing friends. “[One of them] had done exactly what we thought he would never do. He sold his company, built a boat, and he and his wife, and two young kids were traveling for an indefinite amount of time.

“That was in 2012, so they’ve now been a decade on board. We always talked about doing a big boat trip at some point since [Michael] was such a sailor, and both Ally and I loved being on the boat. We looked at each other and said, ‘All right, this is it. This is the time to decide. So we committed to doing it.’”

Ward took a powerful and inventive approach to her memoir—she documented only the first four months of travel, focusing on the monumental planning that went into the trek. Budgeting for the trip, making arrangements to rent their home, planning laundry days, even figuring out how to homeschool on a 300 square foot sailing vessel—all these things and more required the kind of planning you’d expect in a military campaign.

“The idea that a lot of people dream of it, but what does it take to do it? When we went on our RV trip, I wish I had a dime for every person who said, ‘Oh, I would love to drive cross country.’ We would have gone back and forth 10 times on the proceeds. The difference between ‘I wish we could do it’ and ‘We’re doing it’ is that messy middle part, the planning.

“You have to not only know what your map looks like, but also where do you stop for the night? Do you have a dog? Do you have to make a reservation at an Airbnb that takes dogs because there are no hotels in the vicinity? What are the things that are going to trip you up along the way?

That kind of planning can apply to anything. “I would love for this book to be an inspiration on far more than sailing. I even say [in the book], ‘I’m a gardener, not a sailor.’”

The title Crew of Three: How Bold Dreams and Detailed Plans Launched Our Family’s Sailing Adventure might suggest Ward and her family made the trip alone, but the book highlights the large community of sailors—and in many cases, sailing families—they connected and spent time with during their travels.

“There’s a subculture of cruisers that most people have no idea exists. There’s a thing called buddy boats, and it’s not limited to just kid boats, but when you have a kid on board and she’s an only child, you search out other boats with kids. Buddy boats can travel together. They may meet up in an anchorage and hang out and explore and see what’s on each island. They may just hang out for a couple of days, they may hang out for a couple of weeks, they may travel extensively for a month or so.”

That this journey could become a book occurred to Ward during the trip. “I have always known I had a book in me. I have been writing forever, and in college, I studied both business and English. I didn’t want to be a teacher, but I knew that my words needed to go somewhere, and I didn’t know how to do it. And like every other self-deprecating author, I have impostor syndrome. ‘No one’s going to want to read my work’ and all the things that pretty much every artist goes through.”

Since Ward and her family have been back in Mattapoisett, they found their old life “didn’t fit anymore. My husband was sitting in Ohio at a computer all day under fluorescent lights. We had promised our daughter that we would stay put and work for the six [remaining] years of junior high and high school, and four more years for her to finish up college. He came home after that very first week and said, ‘I don’t think I can do this for 10 more years.’ I said, ‘What else do you want to do?’ So now we’re out of the consulting world, running a literal mom and pop oyster farm.’

But Ward’s journey to document their voyages doesn’t end with releasing a book and starting an oyster farm.

“My book is very detailed on the planning side, but it ends four months into our trip.” During the entire two-year journey, “we sent postcards home to ourselves. When I got home, I was startled to see over 300 postcards. Each one was a little snapshot in time of what we were feeling, thinking, and doing, where we were and who we were with. What I’m launching simultaneously with the book is [an online travel journal] called ‘Love, Us,’ which is how we signed the postcards.”

As for the youngest member of their crew, now in college– where is Ally attending school? “The University of Glasgow,” Ward says, “because apparently, when you raise a traveler, she travels.”

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