My girlfriends drag their kids to the next Pirates of the Caribbean installment for a two-hour date with Johnny Depp; their husbands go to fantasize about the pirate life. So, buy your mate a berth on the Brilliant, a 1932 schooner, and set sail from Mystic Seaport for an overnight, plying the waters of Block Island Sound. Seven adults and crew raise the sails, cook in the galley and swab the deck of this historic, refurbished yacht (albeit with open sleeping quarters and traditional heads). No previous sailing experience required. Family trips and kids sailing camps offered, too. Weekend on the Brilliant: September 11th and 12th, $360 members, $410 non-members.