Where The Asphalt Ends - Lana'i
The Hawaiian island of Lana'i is not for the posh, it's for the rugged. With only 30 miles of paved roads (which basically break down into 3 actual roads) and 400 miles of unpaved roads stretching in every direction possible - the island requires you to have a 4 wheel drive to get around it's rugged terrain.
There's only one car rental agency in town located and run by the one gas station in town. Get a old beat up jeep, put on old clothes that you have no attachement to and get lost on the red dirt paths and sandy beach road.
The pictured road leads to Polihua Beach at the north end of the island and it will be full of bumps, bruises, and dirt. Some true off-roading fun!
More information on Polihua Beach: