11 Favorite Vacation Spots of Trump, Obama, and Other U.S. Presidents

3. Martha’s Vineyard, Massachusetts

President Bill Clinton stands by a lighthouse

Former President Bill Clinton favored Martha’s Vineyard. | Tim Sloan/AFP/Getty Images

Massachusetts island Martha’s Vineyard has been a favorite vacation spot for two recent presidents. As Boston Magazine reports, “Over the past 20 years, Vineyard locals have had the unique privilege of hosting two presidential families: first the Clintons, then the Obamas.” The Los Angeles Times reports that to many Martha’s Vineyard residents, the presidents’ presence on the island was “no big deal.” According to the newspaper, the remote nature of the island has drawn many presidents to it.

Former President Ulysses S. Grant learned of the island during the Civil War and put it on the map by vacationing there in 1874 during his presidency. And former Presidents Chester A. Arthur and Grover Cleveland both visited, as did Franklin D. Roosevelt.  And while former President John F. Kennedy maintained a compound in Hyannis, Massachusetts, across the sound on Cape Cod, he liked sailing near the Vineyard. Former first lady Jackie Kennedy made appearances on the island and later bought a remote property there. Since the Kennedys, the Vineyard has drawn mostly Democratic presidents. The Clintons revived its status as a presidential retreat, and the Obamas enjoyed the community’s familiarity with the idea of spotting the president and his family around town. 

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