Lana'i City, Lana'i
Formerly "The Pineapple Island", Lanai is Hawaii's most exclusive and private island. Not a single traffic light, but a little bit of gas - one gas station charging just under $6.00 a gallon. Jeep rentals are difficult to come by and cost $150 per day. Approximately only 30-35 miles of paved roads, the rest is unpaved rough roads and red dirt / thick sandy roadways, accessible ONLY by 4-wheel drive. Yes, to say it's an adventure is an understatement.
Lanai is the island Bill and Melinda Gates were married on, and was purchased by Oracle's Larry Ellison.