I’ve seen proposals on boats, mostly on the bow, in New York, as I sailed past the Statue of Liberty. Nothing memorable like what happened late this summer in Italy. I was chartering a fun group—three couples, all friends, from California—around the Aeolian Islands. One of the couples wanted to hike Stromboli; the guy was a geologist and especially keen. But our sail there took longer than expected because we came upon a pod of dolphins—a good omen at sea—and followed them. I noticed the guy getting angsty. “Boy,” I thought, “he really wants to climb that volcano!” It was late in the day and hot when we got there, but the two of them took off. When they came back down, he was grinning, and she was giddy and had a new ring. He’d brought her to the top of the volcano, where the lava had hardened from a recent eruption, and gone down on bended knee. We all cheer. The chef and I poured out Champagne, and we sailed around Stromboli to share the view they both saw when she said yes. The couple called their families from the boat with the volcano in the background, which felt especially poetic. It was really emotional. I cried for a moment. —Charlotte Matthews, captain for the yacht charter company Sailing Collective.
The vacation romance
My mom passed away in May 2018. We were super close, and I thought, She wouldn’t want me to be here wallowing. Shortly after she passed, I was talking to one of my best friends, Joshua, who’s always going to Jamaica, and he said, “Ash, I’m going to send you a ticket. It’s happening.” So we get to Jamaica, and Joshua and I were on the beach one day trying to find a boat to do water sports. All of a sudden, this man came up to us and said, “Do you guys want to go on this boat?” We were like, “Yes!” And he called me beautiful and said I could go on board anytime. His name was Kevin. He gave us his number, and a few days later, we all ended up going out on the boat with him—it turns out that he was the owner of the boat-charter company. I wasn’t really looking for anything at the time, but the two of us hit it off that day. We spent the rest of the trip together, and two weeks after I got home, I was back on a plane to Jamaica to see him. Within three months, we were engaged, and we got married in Montego Bay, Jamaica, just nine months after that. —Ashley Tate-Gilmore, former director of the White House travel office for President Obama and CEO of the travel-concierge service company Fortis Global.
This article appeared in the March 2022 issue of Conde Nast Traveler. Subscribe to the magazine here†