Though not quite as fast as a helicopter or a private jet, a membership with Barton and Gray gets you unlimited, year-round access to a fleet of tricked-out, fully staffed yachts. In the summer, this means stops in Martha’s Vineyard, the Hamptons, Nantucket, and more; winter harbors include Miami, Sarasota, and numerous islands. Annual fees are steep—like $30,000-to-start steep.