The choice of Martha's Vineyard, late as it was, seems in retrospect to have been inspired. It may be the one place in America Mr. Clinton could go without any danger of running into anti-tax protestors, anti-abortion protestors, or anti-gay protestors. The Vineyard is a redoubt of Sixties liberalism; even the island's one radio station plays mostly the music of that era. The waitress-pardon me, waitperson-who attended the President and his party at the fabled Black Dog Tavern said she had marched on Washington but had never before met a President. She was thrilled. So was nearly everybody else, to judge by the myriad of welcome signs posted all over the place. The only message that had even a faintly discouraging word was nailed to a tree along one of the island's by ways. "Bill," it said, "we know you're trying."
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Also I seem to recall the Democratic Leadership Council meeting on islands such as Hilton Head in SC in the early 1990s. The tradition probably goes back to the Jekyll Island meeting to form the Federal Reserve if not earlier.