#RealTravel: They Met and Fell in Love While Sailing in the British Virgin Islands

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A much-needed break led to an unexpected romance for Erin and Ben. (Photo: Erin Duggan Kramer)

Who: Erin Duggan (now Erin Duggan Kramer) and Ben Kramer

Where you met: British Virgin Islands

When: 2012

Relationship status: Married for one year and three weeks!

(As told by Erin)

After a particularly grueling summer at work, during which I had to cancel all of my vacation plans, colleagues and friends started suggesting (and then demanding) that I take some time off. The sailing club I belonged to (mostly in name and dues only, as I rarely made time to sail) was having a winter regatta in the British Virgin Islands. I was hesitant to go because I didn’t know anyone going on the trip. But I signed up and asked our skipper if I could fly down with him.

On the flight, he mentioned that his good friend Ben had moved from New York City to St. Thomas the year earlier, to escape the hustle and bustle and to work on boats. “He’ll meet us for a drink,” the skipper said and went back to his book.

The day before picking up our boat on the island of Tortola, we all headed to the bar at our hotel in St. Thomas. As I was sitting with the woman who was to be my cabin-mate (and is now one of my best friends), this cute guy walked over, sexy blonde in tow, and introduced himself as Ben. I assumed he was spoken for, so it was easy to relax and listen to his hilarious stories of tourists and sailing.


Erin and Ben bonded over sailing. (Photo: Erin Duggan Kramer)

The next morning on Tortola, one of the men who was sailing on another boat in our regatta swam across the pool to me, popped his head up, and said, “Hey, Erin, I’ve got a message from Ben on St. Thomas.”

“He couldn’t have meant it for me,” I replied.

“Yes,” he confirmed. “He wanted me to tell you he’s a cool guy, and you should get to know him. He’s going to meet your boat on Jost Van Dyke on Thursday. He’ll see you at the Soggy Dollar Bar.”

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I thought for sure he had the wrong person, but my new friend was insistent and told me that Ben was single. Ever the skeptical New Yorker, I wasn’t going to hold my breath.

Sailing around the islands was incredible — the islands’ beauty was matched by the camaraderie of my crew mates. There were nine of us on board, and we clicked immediately. At night we anchored with the other boats and swam, explored the islands, and hosted boat parties. Smartphones were banned from public spaces, and no one talked about work or life back in the real world. After years of intense work, I was fully relaxing.

Ben took the lead in getting Erin’s attention. (Photo: Erin Kramer)

As if the trip couldn’t get better, when Thursday rolled around, we sailed to Jost Van Dyke. I walked up to the beach bar to get a round of Painkillers for the crew, and who was sitting at the bar but Ben from St. Thomas. “I told you I’d be here,” he said with a gorgeous smile. “What took you guys so long?”

It was the first of many pleasant surprises.

(Photo: Erin Duggan Kramer)

We sat by the beach (with Ben high-fiving an old French jogger who ran by every five minutes in a red Speedo), and he decided to sail with us for the last few days of the trip. Watching him teach the crew the finer points of sailing showed me the caring and kind soul behind the hilarious sense of humor. I was smitten, and so were my new friends, who let him join us for the rest of the trip.

By the time we were back on land in Tortola, we both knew that we wanted to see each other again. “Even if all I can do is drive you to the airport, please call me when you get to St. Thomas,” he said.

Back at my hotel, I continued to think about him. Would it be crazy to see him again? Surely this would never work out. I was leaving in two days, and we lived far apart. It’ll never work. It’ll never work. What’s the point?

And then my cell phone rang. It was Ben from St. Thomas.

The couple got to know each other by sailing in the British Islands. (Photo: Erin Duggan Kramer)

“Look,” he said, “I’m just going to put this out there. I really like you. Stay for a day, stay for a week, stay forever. Come see me.”

What the hell, I told myself, I’m a girl with a credit card, and if this doesn’t feel right after a day, I can always check into a nice hotel and relax by myself or with other friends down in the islands. “It will never work” became “Take a chance.”

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So I called my boss and asked him for a little more time off, which he generously gave me.

Over the next week, Ben and I spent the days on the beach, telling each other about our families, our closest friends, our childhoods, and other important details about our life. At night he showed me his favorite island spots; we ate and drank and rolled a month of dating into one week.

By the time I was through security in the tiny island airport, we had already spoken on the phone. That night we started what became nightly three-hour phone calls and FaceTime sessions. Two months later he moved back to New York City, and just shy of our one-year anniversary, he proposed to me on the dock in front of my family’s house in Maine.


Erin and Ben on their wedding day (Photo: Erin Duggan Kramer)

On our honeymoon last summer we sailed along the Maine coast and up to Canada. It was just the two of us and the perfect way to start our newest adventure. I’m looking forward to more adventures together, big and small. And teaching our future kids how important it is in life to take chances — and, of course, learn how to sail.

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