Routes to the Sailing Life
A look at how five families broke free and went cruising.
|Crew: 40-somethings Ben and Molly Doolittle, 10-year-old Mickey, 7-year-old J.P.
Boat: 1984 Catalina 38
Started Cruising: July 2011
Hailing port: Sacramento, California
Short-term plans: Headed for Central America
Long-term plans: The U.S. Eastern Seaboard
For Ben Doolittle, cruising was a life-long dream. He got a taste of it in his 20s, then remained focused on the goal to get out here again. When he chose his career, he decided to sell insurance, knowing that ongoing payments from residuals would help to sustain a cruise.
For Molly Doolittle, a former public-school teacher, cruising is a way for her boys to learn through real-world experience. “I took our oldest son to the ballpark on opening day a few years ago,” she said. “Two old men we sat next to asked Mickey why he wasn’t in school. Mickey told them how much he loved baseball and how his mom had let him skip school to catch opening day in person. The two nodded and looked at my son and one said, ‘Well, you’ll learn more here than you would in school.’ I thought he was dead on.”
The two parents report that the transition for their family has gone smoothly. The amount of time they spend together has increased exponentially, given the living, eating, sleeping, and playing together that they do every day. The boys love the wildlife encounters afloat. Molly is happy that, in addition to exposure to dolphins and turtles and whales, her kids are seeing firsthand that following a passion and living a dream are possible. She’s come to thoroughly enjoy sailing and looks forward to the night passages. The only concern she and Ben have is how to re-enter “normal” society when this is over.
When I asked about the advice they’d give others, both said that overcoming fear is an important step. They said it’s easy to get lost in the what-ifs related to injuries, storms, falling overboard, and running out of money. But once you consider how dangerous it is to drive your car on a Southern California freeway, fear is no longer a reason for not going. And you have to be ready to go: “We found a screamin’ deal on an older Catalina 38,” said Ben. “We were patient, and the right boat came along. The key was being ready to pull the plug on our life and go. When that time came, we pulled the plug and left.”
Molly was quick to note that as much fun as they’re having, cruising isn’t for everyone. “Some people would truly be miserable living this life. That’s what I’d like my children to learn as well: What works for some people doesn’t work for others. Don’t judge it.” Ben agreed, saying that taking off to live and travel as we do—on water or land—is pretty rare in all cultures. “It’s a weird, unique group of people who choose to do this,” he said. “We’re modern-day gypsies.”
Follow the Doolittles on the blog Doolittle Cruising.