The questions is, in the following setup:
--S--S---C-
where -
represents roads, S
settlements, C
cities, is the 'longest road' at 5, or 8?
I had originally thought 8, but as I read the FAQ:
The Longest Road is a continuous road connecting two intersections, which consists of at least 5 individual road pieces and is not interrupted by game pieces belonging to other players. It has more individual road pieces than any other connecting road of this type.
I'm a bit unsure what is meant by connecting road.
I'm probably a bit hopeful that my original thought is incorrect, as I find it annoying when extra road segments are built, sometimes without even a possibility of a future settlement, for the hope of two points.