From Alaska to the Caribbean with No Finish Line

After setting sail from Alaska in 2019, and now in the Caribbean, the cruising Cross clan has enjoyed countless adventures with a straightforward strategy: “Make it up along the way.” Courtesy the Cross Family

As a well-traveled yachting journalist and sailor, I’m never surprised when I randomly run into an old colleague or shipmate. So, it wasn’t at all remarkable last January in Sint Maarten when I again crossed paths with Andy Cross, a longtime sailing writer and editor at publications like Good Old Boat and Blue Water Sailing. I’d last seen him in pre-pandemic days when we’d bellied up to a bar while covering the annual boat show in Annapolis, Maryland. As we caught up in the Caribbean this time, however, I was startled to hear how far our paths had diverged since then.

With his wife, Jill, and two sons, Porter and Magnus, Andy was living aboard the family’s Grand Soleil 39, Yahtzee, teaching sailing at the Sint Maarten Yacht Club and remotely editing the Pacific Northwest boating magazine 48° North. None of that was particularly startling; there are plenty of cruising clans in the islands. The cool, unusual part was how, and why, they’d wound up there.

“A lot of cruising families we meet are on a one-year plan or a two-year plan,” Andy said. “We’re on, like, a no-plan plan. We’re making it up as we go along.”

With that, the man had my undivided attention. And thus, the whole epic story unfolded.

Jill and Andy, ever since meeting as undergrads at the University of Oregon, have forged a singular, adventurous path. After all, how many couples do you know who served together with the Peace Corps in Ethiopia? Back in Seattle afterward, to save rent, they bought and moved aboard Yahtzee. Lifelong sailor Andy worked as a rigger at West Marine and began making inroads as a freelance writer and editor. Summers were spent roaming the rich, local cruising grounds. The boys arrived. They decided to head north to Alaska, Jill’s home turf. where she landed a job as a therapist and social worker. They ended up staying for nearly three years. In 2019, they made a straight, 10-day shot to San Francisco. “From there,” Andy said, “we just kept going south.”

Currently based in Sint Maarten after years on the go, the ever-moving Cross family—Jill, Magnus, Porter and Andy—is living its best life.  Courtesy Andy Cross

Yahtzee took its sweet time lingering along the coast of Central America. All the Cross lads are surfers, and they spent much of the pandemic era investigating and enjoying surf breaks off uninhabited Mexican islands and along the coast of Nicaragua. Once they got to Panama, it was decision time, and they chose to go through the canal instead of venturing into the Pacific, so they could remain close to friends and family (they keep a van in Michigan for excursions off the boat). They first wandered through and loved the lonely archipelagos off Panama and then all of Costa Rica. In Columbia during hurricane season, they took advantage of the cheap $59 flights to rent a place in the rugged, mountainous interior, yet another fantastic family experience. “We’ve never been in a hurry, ever,” Andy said.

In the Caribbean, it became clear that one of the boys was going to require some serious dental work, which meant setting down roots at least temporarily. “Like in Alaska when Jill went to work, it was like, OK, you’ve got to stop for a while and take care of business,” Andy said. After a bit of investigation, they found a great orthodontist in Sint Maarten, and Andy quickly landed his gig at the yacht club as a sailing instructor, a job he’d enjoyed way back when. Meanwhile, the boys joined the club’s racing team and are regularly out blasting around in the 25-knot trades several days a week in Optimists. “Man, they love it,” he said.

Perhaps fittingly, while I was covering the sporty Diam 24 trimaran class during the Caribbean Multihull Challenge, I couldn’t help but notice a young man crewing aboard one of the top boats in the fleet, Ted Reshetiloff’s Buzz Race Team. Yup, it was 12-year-old Porter Cross, the youngest sailor in the entire event. “He’s so stoked. He’s learned so much this week. He’s the happiest kid in the world right now,” Andy said.

Well, of course he is. Like the whole Cross family, Porter is living his best life.

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