How to Summer Like a Kennedy

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Hyannis Port isn’t a place one stumbles upon. In fact, you almost have to be invited to know where to look.

For decades Hyannis Port has been synonymous with the Kennedys. It was where John F. Kennedy’s parents put down roots for their family in the 1920s, it was home to the Summer White House in the 1960s, and it continues to be a haven where new generations of Kennedys escape their busy lives, trading suits and diplomacy for sandals and sailing.

Less than two hours from Boston, Hyannis Port is a quiet neighborhood in the town of Hyannis, which is on the ocean shore before the northward curve of Cape Cod. The Port, as locals call it, is just over nine square miles, with the post office smack in the middle.

There’s almost nothing to the Port: a tiny yacht club—it doesn’t even have a bathroom—a couple of churches, a beach club, a golf club perched on the highest point. The rest of it is made up of cottages clad in gray shingles and framed by hydrangeas.

The reason most tourists go is to catch a glimpse of the Kennedy compound. As I recount in my new book, White House by the Sea: A Century of the Kennedys at Hyannis Port, Joseph P. Kennedy was drawn to the Port after being rejected by the Cohasset golf club on account of being Irish Catholic. In the late ’20s he was welcomed to the Hyannisport Club, so he bought his family a home on Marchant Avenue, a dead-end street that opens onto Nantucket Sound. The Big House, as they called it, was where the Kennedys escaped Boston (and later New York) for the summer, where the children learned to sail and made lifelong friendships with the neighbors’ kids. It’s where the family came to relax, celebrate, and grieve. (It’s also where Conor Kennedy courted Taylor Swift.)

“Even though the Cape house was our base, and you’d think we would be restless to get away from it now and then, explore other places, that was not the case,” Ted Kennedy once said. “Our whole lives centered in this one place.”

In the 1950s JFK and his new wife, Jacqueline, bought the house right behind the Big House, and Robert and Ethel moved in next door. When JFK was elected president and the world’s lens was turned on Hyannis Port, these three connected properties became known as the Kennedy compound.

Many of the families who lived in the Port back then are still there. It’s the kind of place where people walk barefoot down the street for happy hour on a neighbor’s porch. And the highlight of the season is the July 4 parade, which winds through the streets and concludes with free popsicles at the beach club. The Kennedys always have a themed float; the day feels like stepping back in time to Camelot.

This story appears in the Summer 2023 issue of Town & Country. SUBSCRIBE NOW

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