Spent a day on Lanai this past August. Touring in the Jeep was pretty wild. Shipwreck Beach is pretty cool, although getting there was interesting. People literally live in little huts constructed of plywood right on the ocean. You drive right by their front door en route to the shipwreck. Kids playing in road and all. Hippies from the U.S. mainly. God I hate hippies. The resorts are very well maintained, but the town is run down and outdated. We'll surely return to Hawaii, but likely won't return to Lanai. The resorts are just as nice on any of the other islands. Just my $0.02.
The Road to Hana - a driver's nirvana. Cruise out there, and once you reach the end, start your spirited drive back. One of the most fascinating roads in the world.
Joe