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A Nostalgic Look Back at the Kennedy Family’s Summer Vacations Throughout History
via Vogue · July 24, 2026

A Nostalgic Look Back at the Kennedy Family’s Summer Vacations Throughout History

Take a look at photos of the family vacationing in Hyannis Port, Massachusetts over the years.

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With the summer in full swing and families getting together for barbecues, weddings, and other gatherings, we’re thinking of one of America’s most famous families: The Kennedys. The political dynasty has long held the fascination of the American public and people around the world, who have followed not only their political moves but their personal lives, and how they spend their leisure time. The Kennedys are known for their large family gatherings on holidays and in the summertime, including their storied Fourth of July parties at the Kennedy Compound in Hyannis Port, Massachusetts. (And of course, their celebrity guests: In 2012, Taylor Swift reportedly attended the family’s Independence Day festivities).

Described as the “Summer White House” during the presidency of John F. Kennedy, the compound—which is made up of three houses on the water—was featured this year in the FX television series Love Story, renewing interest in a retreat that endures as a symbol of Camelot.

Below, see photos of scenes of the Kennedy family’s vacations, from sailing to golfing and more.

The Kennedy family summering in Hyannis Port, Massachusettes, 1931.

Rose Kennedy with her daughters, from left, Eunice Kennedy, Jean Kennedy, Patricia Kennedy, Rosemary Kennedy, and Kathleen Kennedy, in Hyannis Port, Massachusettes, circa 1935.

Rose Kennedy sailing with her children Ted, Jean, Joe, Jr., Robert, Patricia, and Eunice, circa 1940.

Jacqueline Kennedy, Eunice Kennedy, and Jean Kennedy chat on the porch, June 1953.

Jacqueline Kennedy on the porch at the Kennedy compound, June 1953.

John F. Kennedy and Jacqueline Kennedy sailing in Hyannis Port, Massachusetts, June 1953.

John F. Kennedy and Jacqueline Kennedy playing football on the grounds of the Kennedy compound, June 1953.

Eunice Kennedy, Jacqueline Kennedy, Jean Kennedy, Patricia Kennedy, John F. Kennedy, and Edward Kennedy sailing in Hyannis Port, Massachusetts, June 1953.

Jacqueline Kennedy playing baseball with Edward Kennedy on the front lawn, June 1953.

Jacqueline Kennedy and John F. Kennedy in the living room in Hyannis Port, Massachusetts, June 1953.

John F. Kennedy and Jacqueline Kennedy getting ready to play tennis, June 1953.

Jacqueline Kennedy comforts daughter Caroline Kennedy on a rainy day at the beach in Hyannis Port, Massachusetts, circa 1960.

John F. Kennedy with daughter Caroline Kennedy in Hyannis Port after the Democratic Party named him its 1960 presidential candidate, August 1960.

Robert F. Kennedy poses with his children: Robert F. Kennedy, Jr., David Kennedy, Kerry Kennedy, Michael Kennedy, and Courtney Kennedy, 1962.

Jacqueline Kennedy and her husband, then-Senator John F. Kennedy sit on a lounge chair at their summer home. Jacqueline reads to her daughter Caroline from a book.

Jacqueline Kennedy and John F. Kennedy with their children, John F. Kennedy, Jr. and Caroline Kennedy, 1962.

John F. Kennedy, Jr. plays with his dog Shannon, while Jacqueline Kennedy chats in the background, 1963.

Marion Markham and Courtney Kennedy playing during a summer gathering at the Kennedy compound, July 1963.

Maria Shriver and Caroline Kennedy play on the presidential yacht Honey Fitz, during a cruise in Hyannis Port, Massachusetts, 1963.

Caroline Kennedy talks to her dad aboard the presidential yacht Honey Fitz, during a cruise in Hyannis Port, Massachusetts, 1963.

Charles Spalding, Prince Stanislaw Radziwill of Poland, Jacqueline Kennedy, and John F. Kennedy in a convertible in Hyannis Port, Massachusetts, 1963.

John F. Kennedy, Jr. at the wheel of a speedboat in Hyannis Port, Massachusetts, 1963.

Rose Kennedy playing golf on the Kennedy compound, 1970.

Senator Ted Kennedy and his mother Rose Kennedy, return from boating in Hyannis Port, Massachusetts, July 1972.

John F. Kennedy, Jr. heading to the beach in Hyannis Port, Massachusetts, 1979.

Members of the Kennedy family chat during gathering at the Kennedy compound in 1980.

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