Lanaʻi

Although Lanaʻi is the most central of the Hawaii islands – on a clear day you can see five islands from here – it's also the least 'Hawaiian'. Now-closed pineapple plantations are its main historic legacy, and the locals are a mix of people descended from immigrant field workers from around the world.

Its signature (imported) Norfolk and Cook Island pines give the island a feel that could just as well come from a remote corner of the South Pacific. And therein lies the charm of Lanaʻi, a small island (at its widest point only 18 miles across) that's an off-the-beaten-path destination. Hidden beaches, archaeological sites, oddball geology and a sense of isolation let you get away from it all, without going far.

Of course, looming over Lana‘i is billionaire owner Larry Ellison, whose efforts to transform the island have proceeded in fits and starts.