The Kennedys, who were basically the American equivalent of a royal family, took epic vacations. Whether it was a trip to the family compound in Hyannis Port, Massachusetts or a beach getaway in Cannes, France, they made their vacations look like the American dream personified: casual chic clothing, sports games all day, and sumptuous food for dinner.
The reality was, of course, more complicated. But the photos of the Kennedys before, during, and after their trips often show them in their most relaxed moments. In particular, the vacations of the First Family (President John F. Kennedy, First Lady Jacqueline Kennedy, and children Caroline and John Jr.) received prominent media attention while the young family was in the White House. The public loved looking at these photos, and they're still a fascinating throwback today. Below, 32 gorgeous photos of the Kennedys on vacation.
October 1963
Per the original photo caption, Jackie was returning home from a "dream vacation" in the Mediterranean and Morocco (for context, this would not have been long after she'd lost a premature infant son). Caroline is 5 and John Jr. is 2 here, with John in the rear as the family disembarks from the plane.
March 1967
Jackie and her sister, Princess Lee Radziwill (wearing sunglasses in the backseat) sit in a car with their children (Anthony Radziwill, John Jr., and Caroline, from left to right) as they head to their Easter vacation at a "jet set resort," per the original caption.
August 1962
Here, the Kennedy family has just returned from a vacation in Italy. Young Caroline is talking animatedly to her father (one imagines about vacation shenanigans) and looks cute as a button in her double-breasted coat dress and shiny white gloves. Now that's a travel outfit.
August 1993
In 1993, during a private boat trip around Menemsha Harbor on Martha's Vineyard, Jackie (then known as Jacqueline Kennedy Onassis, and who mostly lived very privately) is seen vacationing with President Bill Clinton, First Lady Hillary Clinton (both on the right), and Senator Edward (Ted) Kennedy (on the left).
August 1993
During their 1993 vacation, Jackie and Caroline put their feet up and relax on the deck of their yacht. According to the original caption, "During a vacation on the island of Martha's Vineyard, the Clintons were invited by members of the Kennedy family for a cruise aboard the Kennedy boat 'Relemar.'"
January 1963
Per the original photo caption, the Kennedys were returning from a holiday vacation in Florida when Caroline's Welsh terrier, Charlie, went rogue and ran off his leash. Caroline caught up to him and re-secured him, while a crew member of their helicopter came by to assist. It's a sweet little moment!
October 1961
While in the Narragansett Bay in Rhode Island, the Kennedy family (John, Jackie, and Caroline) sit aboard the Presidential yacht "Honey Fitz" (named after John's grandfather), before heading out on a cruise. Of the three, Jackie probably looks the most vacation-ready.
November 1960
John, then President Elect, carries Caroline as the three de-plane. Jackie, pregnant, would remain in their home in Georgetown while John would continue on to a vacation in Florida. This photo was taken in November 1960; John Jr. would be born later that month.
June 1953
There are a number of photos from a vacation at the Kennedy compound in Hyannis Port, Massachusetts, as a part of a LIFE Magazine story. Titled "Senator Kennedy Goes A-Courting," it was the first cover to feature then-Jacqueline Bouvier (pictured with the reporter). She and John would marry that September.
June 1953
From the LIFE feature debuting John and Jackie's relationship, the couple have a discussion with Patricia Kennedy, John's sister, while the family is on vacation. Patricia's at the wheel; Jackie holds onto her summer hat while John stands behind the car.
June 1953
The Kennedys: avid sailing enthusiasts! From left, Eunice Kennedy, Jackie, Jean Kennedy, Patricia Kennedy, John, and Edward Kennedy head out on the water together. The two men busy themselves with the sailboat while Jean keeps a hand on the tiller and Jackie gazes back at the photographer.
March 1970
Here in 1970 (two years after her wedding to Aristotle Onassis), Jackie visits Mayan ruins in Palenque, Mexico as part of a trip across the country. Jackie's fashion was the stuff of legend, but her casual style—here wearing jeans and a knit top—was particularly enviable.
December 1964
Vacationing in Aspen, Colorado, Jackie, Caroline, and John Jr. trudge through the heavy snow on Buttermilk Mountain. Jackie carries John Jr. while Caroline walks ahead to the ski lodge as the snow falls. (John had been dead about a year when this photo was taken, and the family didn't do many public appearances.)
January 1966
Here is a close-up shot of Jackie and daughter Caroline as they ride a sled in Gstaad, Switzerland. Jackie, Caroline, and John Jr. were often photographed on the slopes or at the lodge during vacations when the children were small (the whole Kennedy family was avid skiers).
November 1963
Jackie and Caroline are in the foreground; John is in the back with reporters on the way to a vacation in Palm Beach, Florida. Jackie carries the 1960 book The Purpose of American Politics (which is a particularly nice touch, considering her role as First Lady).
September 1963
Here in Newport, Rhode Island, John Jr. sits on Jackie's lap while John drives the family out of Bailey's Beach on the way to a cruise on the family boat Honey Fitz. Apparently Caroline is also in the car (not pictured). Their thick knit sweaters and particularly John Jr.'s Fair Isle design is very New England.
January 1968
Jackie is on vacation on the Greek island of Skorpios with John Jr. and Caroline (this is around the same time she would marry again, to Greek-Argentine business magnate and old friend Aristotle Onassis). Barefoot and wearing a sleek, simple outfit of white cigarette pants and a black top, Jackie dons her trademark oversize sunglasses.
Circa 1935
This cool vintage photo shows that Kennedy vacations didn't start with John and Jackie. From left to right, Patricia, Jack, and Eunice Kennedy pose while in Cannes, France, spending a holiday with their parents (as children to the U.S. Ambassador to Great Britain, news of their international vacations was already making headlines).
June 1953
This is from the LIFE Magazine feature from 1953, and it captured photos of everyday life while the engaged couple were vacationing on the compound. Here, they play baseball with the family. Jackie's look of concentration and effort is really impressive here!
April 1963
Here, attending a private mass while on vacation in Palm Beach, Florida, John takes the lead holding Caroline's hand in front, with Jackie and John Jr. behind them. They're dressed conservatively as befitting the occasion, with Jackie in a pretty lace veil.
January 1966
At a ski resort in Sun Valley, Idaho, Jackie and Caroline smile and joke in the open air. The family was apparently visiting Senator Robert F. Kennedy, whom Jackie was close with. Per usual, their cozy knit sweaters, and particularly Caroline's patterned knit, look equal parts chic and cozy.
June 1953
The Kennedys could be a boisterous bunch. Here, from left, Jean Kennedy, Jackie, and Eunice Kennedy point and exclaim at something (perhaps something just off shore?) while casually sunbathing on the bank. This was another shot from the LIFE Magazine feature.
June 1953
In one of her most recognizable photos before she became a wife and subsequently First Lady, Jackie poses on the Kennedy compound in an awesome outfit—a small, delicately printed top, a-line shorts, and a straw hat. She looks carefree and happy here.
August 1960
As they pause to enjoy the breeze, Jackie and John are on vacation with Caroline in Cape Cod before John goes on the Presidential campaign trail. Caroline clutches a little toy in her hand as they all look out towards the boats in the harbor. Jackie would give birth to John Jr. in November.
February 1961
An incredibly sweet moment: Caroline Kennedy, with a bow in her hair, runs on the lawn during the family's vacation in Palm Beach, Florida. These candid photo-ops were not uncommon, since a lot of viewers were interested in the young family living in the White House.
March 1967
Being aided by a staffer baiting hooks for them, John Jr. and cousin Anthony Radziwill go fishing in the Pacific Ocean. The two families (Jackie and sister, Princess Lee Radziwill) were vacationing over Easter, and the two boys look completely, utterly attentive.
June 1953
From the 1953 LIFE Magazine spread, Jackie and John are interviewed for the story while inside the Kennedy compound in Hyannis Port. Jackie is intently listening to the interviewer while John puts his foot up and fiddles with what looks like a string.
Circa 1931
It's the whole Kennedy clan in Hyannis Port! Joseph P. Kennedy Sr. and wife Rose sit in the middle with eight of their nine children (plus their dog) around them; it looks like John is upright on the left of the photo. Edward (Ted) Kennedy, the youngest, was not born until 1932.
June 1967
Here, pictured in 1967, Jackie is on vacation in Ireland doing some horse-back riding with her kids (not pictured). Her style is perfectly "outdoorsy chic," with cigarette jeans, a matching navy top, and her trademark oversized sunglasses over her eyes.
June 1967
Shown with John Jr., Jackie takes a moment in the middle of the ride to connect with her son. Apparently, they were visiting cousins on the Fitzgerald side of the family, and Caroline (not pictured) rode a pony belonging to her cousin named Danny Boy.
August, 1962
While vacationing at a seaside resort in August 1962, Jackie gazes up at a sign welcoming her and wishing her a happy holiday. She and daughter Caroline, both in bathing suits, stand on stone seaside steps, presumably on the way to or from the beach.
June 1953
This may be the most memorable Kennedy vacation photo ever taken: then-Jackie Bouvier sailing with John Kennedy in Hyannis Port, Massachusetts, a few months before they got married. A version of this photo made the LIFE Magazine cover, and it depicts the couple in a sweet, simple moment.
