Holiday Like POTUS: Presidential Vacation Hot Spots

As President Obama and his family vacation in Martha's Vineyard, we're taking a look at favorite presidential getaways, past and present.
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Wendy Mead
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As President Obama and his family vacation in Martha's Vineyard, we're taking a look at favorite presidential getaways, past and present.
Barack Obama Photo

President Obama hits the golf course in Martha's Vineyard on August 8, 2015.

What happens when Washington, D.C. gets too hot in August? If you're the nation's top boss, you know it's time to flee the political scene and chill elsewhere. President Barack Obama already has his great escape on the books with a planned trip to one of his favorite summer haunts. And he is just one in a long line of our leaders to give up the White House for a beach house. 

Our first president George Washington didn't travel far, choosing to relax at his home Mount Vernon in Alexandria, Virginia. Cape May, New Jersey was another popular destination for the likes of Ulysses S. Grant and Benjamin Harrison. Let's take a look at some other popular getaway destinations of America's commander in chief, past and present. 

Long Island Getaway

The Hamptons may be the place to be now, but for President Theodore "Teddy" Roosevelt it was all about Oyster Bay, Long Island. Roosevelt had vacationed in the Oyster Bay area as a child and later bought property there for his family. In the 1880s, he bought land on Cove Neck in Oyster Bay. Roosevelt originally planned to live there with his first wife Alice, but she died in childbirth in 1884. With his second wife Edith and his daughter Alice from his first marriage, he eventually moved into the home that became known as Sagamore Hill. This is where he and Edith raised Alice and their five children. 

Theodore Roosevelt Family Photo

The Roosevelts posing for a family picture at Sagamore Hill in 1907. Clockwise from left: Kermit, in riding clothes, Edith, Teddy, Jr., Quentin perches on his mother's chair and Theodore Roosevelt holds Archie with the family dog at their feet.  (Photo: Library of Congress)

In 1901, Roosevelt assumed the presidency in the wake of President William McKinley's assassination. His beloved Sagamore Hill home soon became his summer sanctuary. From 1902 to 1908, Roosevelt spent his presidential summers there. He could never completely escape work, however. Roosevelt entertained foreign visitors and gave speeches from his yard. In 1905, he even helped end the Russo-Japanese War by holding peace talks in his library. Roosevelt returned to Sagamore Hill after his presidency ended, and it is where he passed away in 1919. 

Theodore Roosevelt Sagamore Hill Photo

Sagamore Hill, Theodore Roosevelt's summer sanctuary in Oyster Bay, Long Island.

Today the Queen Anne -style house is a National Historic Site and is open to the public. Visitors can check out Roosevelt's many hunting trophies and his eclectic library of roughly 8,000 books or wander the expansive grounds. 

Cape Cod, Kennedy Style

For many presidents, vacation means a time for family. And it helps if your family has its very own compound to visit. President John F. Kennedy liked to holiday at his family's coastal estate in Hyannis Port, Massachusetts. According to Forbes magazine, he once said that he went there "to be revived, to know again the power of the sea, and the Master who rules over it and all of us."

John F Kennedy and Family Photo

President John F. Kennedy, First Lady Jacqueline Kennedy, and their children John, Jr. and Caroline, at their summer house in Hyannis Port, Massachusetts on August 4, 1962. (Photo: Cecil W. Stoughon ([1]) [Public domain], via Wikimedia Commons)

His parents, Rose and Joseph P. Kennedy, bought the waterfront property in the late 1920s. Over the years, neighboring homes were bought by other family members, including John F. Kennedy himself. During his time as a senator and as president, Kennedy sought out the peace and privacy the compound provided him and his family. The place was also perfect for docking his presidential yacht, the Honey Fitz. Today, the compound is closed to the public, but nearby Hyannis offers a number of Kennedy-related activities. Stop by the John F. Kennedy Hyannis Museum or visit the JFK Memorial at Veterans Beach. 

John F and Caroline Kennedy Photo

Caroline Kennedy and her father President John F. Kennedy aboard the "Honey Fitz" in Hyannis Port. (Photo: Cecil W. Stoughton (1920 - 2008) (Cecil Stoughton, White House Photographs NARA) [Public domain], via Wikimedia Commons

Maine's Rugged Coastline 

George H. W. Bush, like many generations of Bushes before him, sought solace from presidential pressures at the family homestead known as Walker's Point in Kennebunkport, Maine. This beautiful peninsula on a rocky stretch of New England coastland has been in the 41st president's family since the late 1800s. The main building in the Bush compound dates to the 1920s. The place features many luxuries, including a pool and its own boat dock. One of Bush's favorite activities over the years has been cruising the nearby waters on a high-powered boat. 

George H.W. and Barbara Bush Photo

President George H.W. Bush and First Lady Barbara Bush pose with their grandchildren on the rocks at Walker's Point in Kennebunkport, Maine on August 18, 1989. (Photo: David Valdez, 1949-, Photographer (NARA record: 4097323) (U.S. National Archives and Records Administration) [Public domain], via Wikimedia Commons)

Oddly, his son and fellow president George W. Bush didn't feel the call of Maine. Instead he traded Washington, D.C. for even hotter, albeit less humid, climes. Bush liked to spend his summer break at his ranch in Crawford, Texas. But that didn't stop him from holding a meeting with Russian leader Vladimir Putin at Walker's Point in 2007. The event was dubbed by the press as the "lobster summit." In 2015, presidential hopeful Jeb Bush tried to see if some of the Walker's Point magic could boost his campaign for the 2016 Republican presidential nomination. He held a fundraiser at his parents' home there and a house is building built on the compound for him and his family. Unless you score an invite, there's no way in to Walker's Point. But there is a turnout near downtown Kennebunkport where you can park your car and snap a selfie with this famous estate in the background. 

Bush Compound Kennebunkport Photo

The Bush compound in Kennebunkport, Maine. (Photo: Zollernalb (own work, eigene Arbeit) [GFDL or CC BY 3.0], via Wikimedia Commons)

Martha's Vineyard: A Presidential Playground

Even if you're not part of a political dynasty, you can rely on your friends and supporters to help you land some pretty impressive vacation digs. President Bill Clinton visited Martha's Vineyard, an island off of Massachusetts, several times during his presidency. He liked to hit golf courses, including the Farm Neck Golf Club, and was known to hit some of the shops as well. Clinton also liked to visit with friends on the island, including actors Mary Steenburgen and Ted Danson.

Bill and Hillary Clinton Photo

Bill and Hillary Clinton biking in Martha's Vineyard in 2011. 

Following in Bill Clinton's footsteps, President Barack Obama has taken several vacations on Martha's Vineyard. The island won him over in 2007. According to the Los Angeles Times, he said that "I can wander around in shorts and not shave in the morning, and no one talks about it." For several years, he rented Blue Heron Farm, a huge estate in the island town of Chilmark. The property, which boasted a tennis court, golf course and swimming pool among its many amenities, later sold for more than $20 million in 2011.

Obama Family Photo

First Lady Michelle Obama, President Obama and their daughter Malia go for a ride in Martha's Vineyard in August 2014.

Obama has enjoyed some of the island's fine dining options over the years. He and Michelle had a romantic dinner at the Beach Plum Inn in Menemsha and joined friends for a gathering at the Sweet Life Cafe in Oak Bluffs. And like Clinton, Obama has made good use of the island's golf courses as well. He and his entire family also biked through the Manuel F. Correllus State Forest