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

The Story

All of the recent fervor about “America’s royal wedding”—otherwise known as the wedding of Taylor Swift and Travis Kelce—has us thinking about the other Americans who are often seen as a kind of national royalty: the Kennedy family. Along with their major political power over the years, and the “Camelot” legacy of President John F. Kennedy, the sprawling Kennedy clan has long been a point of fascination for the American public.

Onlookers have long obsessed about everything from the romantic lives of the Kennedys (as illustrated by the popularity of FX’s Love Story, which chronicled the relationship and tragic deaths of John F. Kennedy Jr. and Carolyn Bessette-Kennedy), to their schooling, and the way they spend their leisure time. Perhaps the most iconic symbol of the Kennedy family, outside of political office, is their summer retreat in Hyannis Port, Massachusetts, known as The Kennedy Compound.

Known as the “Summer White House,” the waterfront homes have played host to generations of Kennedys for vacations, weddings, annual Fourth of July gatherings, and more. Below, see photos of scenes from the Kennedy family’s vacations—dating back almost a century.

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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