Five years after sailing south from Alaska and the Pacific Northwest, 48° North Editor, Andy Cross, and his family are making tracks again in the Caribbean.

Flamboyant island-style clothing swayed in the wind under vendors’ canopies, colorful murals adorned brick walls, and streetside restaurants and cafés pumped out smells of delicious French foods. Falling head over heels into the first bakery we happened across, our eyes were bigger than our stomachs marveling at all the delicacies behind glass cases. We wanted it all.

It was our family’s first day walking through Marigot, the small capital city on the French side of Saint Martin, and we were all getting an acute sense of being in a new place—traveling once again, experiencing all the sights, sounds, and people.

From the main part of town, we walked up a steep road and then an even steeper set of steps to the top of Fort Louis. The boys scrambled up to the highest point first and perched themselves under the French flag fluttering in the gentle Caribbean breeze. It looked as though rain was imminent, but it was holding off… for now. When Jill and I followed them up the rock and stone walls that had been built during the reign of King Louis XVI and opened officially in 1789, she said, “This is it, I feel like we’re actually cruising again.”

She was absolutely correct. As I gazed out past the ramparts and cannons that once defended the warehouses in Marigot’s harbor below—where locally made goods of coffee, salt, rum, and cane sugar were stored—I had the exact same feeling. In the distance I could just make out Yahtzee bobbing in the harbor and I couldn’t help but smile. Indeed, we’re back, and the feeling is amazing. 

We all know that every life is filled with trials and tribulations. To me, it’s how you handle them and move forward in a positive direction that matters the most. Over the past two years, our family has endured some serious engine problems aboard Yahtzee that have stalled our cruising plans and put a strain on our budget. The issues started in Colombia, continued in Curaçao, and came to a head in early March 2024 in the British Virgin Islands. The ultimate fix was to cut open and clean out the fuel tanks, remove the engine, have it fully rebuilt, and then reinstall it. If you’re not familiar with the complexity and associated costs of all this, I can assure you it’s no easy undertaking, and takes a village to make happen. The whole ordeal has been beyond stressful, so I’ll spare you the exact details.

Holed up in Nanny Cay Marina on the island of Tortola, we did our best to make the situation a productive and beneficial one for our home and family. The boys made a gaggle of friends at a local surfing beach, which was a favorite weekend destination, and in the marina. A daily ritual developed that had kids knocking on the boat, and then they’d all go play until well after dark before being called in for dinner. Jill and I made friends, too, and found the vast generosity of others on our new island home to be refreshing. Yes, Yahtzee couldn’t move, but that didn’t mean life also stopped. As we always do, we kept going.

On a hot morning in May, our intrepid family of four extracted the engine from Yahtzee, carefully moved it onto a cart on the dock, and put it into the care of a mechanic who had little time, but was willing to help. Soon after, hurricane season arrived and the boat came out of the water for another summer of us hoping for the best in this unpredictable dance with the weather. One tropical storm made its way past the islands, but other than that, we were fortunate to be left unscathed.

Fast forward through three months with friends and family in the States, and another road trip in our van, and it was time to return to the islands and to get the boat ready. The bright red engine had been rebuilt while we were away and I arrived a week before the rest of the family to put it back in the boat. It was an intense week of work in the hot and dusty boatyard, but with more help, I managed to get it done. Yahtzee splashed with a working engine in late October and, the next day, Jill, Porter, and Magnus arrived home. We set to work getting her ready for cruising again and two weeks later, slipped our dock lines and motored out of Nanny Cay Marina.

The moment felt amazing, but also uncertain. How would we do getting into the swing of cruising again as a family? Would the engine hold up after being rebuilt? What else could we expect on the horizon? We didn’t know, all we could do was move ahead.

Accordingly, a weather window popped up to leave the British Virgin Islands, and we made an overnight hop 90 miles southeast to Saint Martin. The engine did its job admirably, the crew was steady, and when we sailed up to a new island as the sun rose, it truly felt like we’d made it. Going ashore in Marigot that day was a monumental moment for our family—indeed, we were cruising again.

Who knows where the winds of change will take us from here and what the next set of trials and tribulations will be that tests our family’s resolve. One thing’s for certain, though, we’ll face it together, and it will all be part of the adventure that we call life.

Note: This article was originally published on SailingYahtzee.com.