One need not be a millionaire to visit Nantucket, but it couldn't hurt. This compact island, 30 miles south of Cape Cod, grew rich from whaling in the 19th century. In recent decades it's seen a rebirth as a summer getaway for CEOs, society types and other well-heeled visitors from Boston and New York.
It's easy to see why. Nantucket is New England at its most rose-covered, cobblestoned, picture-postcard perfect. Nantucket town has the biggest draw for its fine dining, lively bars and one-of-a-kind history you can experience on just about every street. Elsewhere on the island outdoor activities abound. Even in summer you'll be able to find uncrowded stretches of sandy beach. All on an island that is close enough to reach without much hassle, but still feels deliciously remote.