President Obama and First Lady Michelle Obama leave for Martha’s Vineyard earlier this month. During President Obama’s first presidential summer vacation, in 2009, he shared an adorable moment with his niece Savita. President Kennedy, Jacqueline Kennedy, and their children Caroline and John at Hyannis Port in August 1962. In 2010, Michelle Obama and daughter Sasha traveled to Spain. The Clintons, fellow Vineyard fans, return from a summer vacation to the island in 1997. Barbara Bush, alongside both Bush presidents, on a fishing trip off the coast of their Maine family compound in June 2007. President Reagan and wife Nancy on a horseback-riding excursion. The Kennedys with their dogs at Hyannis Port in August 1963. President Franklin D. Roosevelt enjoying a cruise along the New England coast, July 1932.