words :: Kristin Schnelten // photos :: Gillian Montgomery.
For 19 years, Paul Montgomery and his family spent their summer vacations along the lengthy coasts of Europe. Sailing between ports on their 51-foot sloop, sleeping in tiny berths and doing much of their own cooking, Paul saw it as an inexpensive way to travel. But last summer, declaring they’d seen it all, Paul resolved to bring the Dream Catcher back to North America—which required a multi-week crossing, months of planning and an amiable crew.
Paul’s sister Ann, daughter Gillian and son-in-law Will signed on for the crossing, and other family members joined for one last month-long fling around Spain and Portugal. On this final European tour, before they even began the transatlantic leg, they hit their most treacherous seas in a three-day continuous sail through the Strait of Gibraltar.
A narrow stretch of water between Spain and Morocco, the Strait is a tight funnel filled with freighters, yachts, cruise ships, fishing boats—every vessel coming into or out of the Mediterranean Sea. It was here, in the dead of night, when the weather hit.
“This insane gale came out of nowhere and we had the wind on the nose, which made the boat go straight up in the air and then crash down. The wind was so strong, almost blowing us backward,” says Gillian.
The darkness combined with the wind conditions meant high alert for those on watch—work that fell mostly to Gillian, who remembers the most intense moments of the trip: “The little fishing boats had no lights and didn’t show up on the radar. It was like navigating through a minefield, with the boat rattling up and down.”
They made it through without a scratch, sailing on to Morocco and the Canary Islands, where Paul had his own intense moment.
Headed back to the boat after a quick bike ride through town, he misjudged the dock ramp transition and went straight over the handlebars. At full speed, without a helmet. X-rays and scans allayed fears of a broken neck, and Paul brushed it off. “Eleven stitches and a good story later, I was back on the boat. When you get to my age and you live like I do, stuff like that happens.”
Minor as it was, a recent head injury for a captain starting a multi-week sail seemed a bit touchy. And Ann, plagued by weeks of constant seasickness, had her own concerns. At the last minute, the four enlisted a final crew member: Will’s brother-in-law, an ER physician. Arriving with a full bag of emergency medical supplies and the enthusiasm of an experienced sailor, Ben settled into the boat just days before sailing from the Canaries.
The 18-day crossing that followed was, for the most part, smooth sailing. No major storms or mechanical failures—even Ann’s seasickness abated.
“We all had time to slow down and focus. The littlest things entertained us, like the lone bird who lighted on the sail, thousands of miles from shore,” says Gillian.
For Ann, the experience of five extended family members surviving in such a small space for nearly three weeks has parallels to our recent global pandemic experience. “When your whole world as you know it changes—either watching land disappear from you or the WHO announcing a pandemic—your first response is just to hunker down and focus on food and shelter. Then, once those are in place, you can explore the next phase of adaptation.”
The crew’s particular focus on food was part necessity, part entertainment. They ate like kings from their 30-day food supply (they shopped and packed for a worst-case scenario), got creative with their massive bundle of bananas (banana bread for weeks) and tested every manner of fish preparation.
Besides maintaining the boat and strategizing freshwater conservation, their days were quiet as they fished and cooked, cleaned and sailed, read books and watched movies. The highlight of every day was simply gathering in the cockpit to watch the sunset.
Sighting land on the horizon was a bittersweet moment, an end to a long-anticipated adventure. “If I could, I would have turned around and sailed right back across the Atlantic,” sighs Gillian.