“Have you ever lived on an island?”

I poured the rum, dealt the cards and pondered the question.

It was a rainy Havana night. Tropical storm Hermine swirled overhead. Raindrops pelted tin roofs in the alley. Stray dogs barked. Boys played marbles on the sidewalk, despite the rain. Water poured onto the marble staircase of this once-elegant building, as all of the windows along the staircase lacked glass, save one pane per floor. Inside the front door, a few pieces of cardboard lay on the floor, sopping up water.

We played Canasta. My daughter Madeleine and I were in her apartment in the Vedado neighborhood of Havana. Madeleine had spent the summer in Havana studying Spanish. My wife Melissa had done the hard work of traveling to Cuba with Madeleine at the start of the summer and helping her to get established. By summer’s end when I arrived, it was easy: Madeleine was fluent in Spanish, and an expert guide to the city.

In preparing for that trip, I read an article by Wendy Gimbel in which she described Cuban people playing Canasta. That intrigued me, as Canasta had always been a favorite game in my family. Melissa and I had spent many enjoyable evenings playing Canasta with my grandparents.

What intrigued me further, however, was something my mother had told me before my trip. After the untimely death of my great-grandfather, my great-grandmother, in a state of distress, left her two children behind in New York and spent an entire year in Havana. This was news to me. Perhaps, I thought, this tradition of Canasta came from this sojourn to Cuba.

Madeleine and I played cards on the dining room table. I explained the rules of the game, as well as I could remember. While we played, I thought of that question, have you ever lived on an island?

The question was posed to me as one of the essay questions when in 1997 I applied for the land superintendent position with the Martha’s Vineyard land bank commission. My response was, yes — I lived for a year on the island of Manhattan.

While I did not give much thought to the question at the time, I also never forgot it. Now nearly 20 years later, I find that I have spent almost half my life either living on an Island or traveling back and forth to one. That simple question has grown in significance over time. Why? What is it about Islands?

I think there are two key aspects of life on an Island that make the question significant. First, Island life brings one closer to nature. Second, perhaps because of that closeness to nature, Island life helps you understand other Islanders — no matter which island they live on, or when they lived there — as they share a common experience.

Canasta takes time. As we played, I felt a sense of communion with family members — most of whom I never knew — just because they had lived on islands. I thought of my grandmother roller skating toward the Hudson River in Washington Heights, and my great uncle swimming in the currents of Spuyten Duyvil. I recalled my great-great-aunt’s Barbados lilt and the aroma of fish cakes.

And I thought of my distraught great-grandmother, playing cards and drinking rum in 1920s Havana. Had she stayed in an apartment like ours, in a building and a city that was then at the height of its grandeur? Had she played Canasta while a tropical storm swirled overhead, and as the rain beat down, just as it was for me and for Madeleine? What storms swirled in her mind, as she eventually decided to return to her children in Manhattan?

Living on an Island for any length of time bonds you to other Islanders. We know the feeling of hurricanes, whether their winds are doubling over Havana palms or Edgartown oaks. We know the sound of the foghorn and the bell buoy. We know isolation, when the boats can’t run, we know what it is to be stranded. We know, too, the wanderlust that Islands stir, from the constant sight of travelers coming and going, from planes landing and departing, from ferries docking and sailing off.

Island living forms bonds across the generations. Perhaps a century from now, a great-granddaughter might think of her ancestors, who waited out Atlantic storms by a woodstove in a place called Quansoo, playing Canasta.

Adam Moore is executive director of the Sheriff’s Meadow Foundation. A version of this essay appears in the Sheriff’s Meadow newsletter.