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Long Island, New York
Wonder what would it have been like to mingle with the Vanderbilts and the Doubledays at Gatsbyesque gatherings on the Hamptons in the 1920s? A stay at the Montauk Yacht Club Resort should give you a good idea. The historic club maintains the same feel of casual elegance and exclusivity, overlooking a yacht-filled marina where Lindbergh once docked his seaplane. While you may not hail from New York aristocracy, you can always pretend.