On a trip through Sicily with my SO, I was driving through mountain roads in a compact rental car, and using a combination of an old GPS unit provided by the agency and Google Maps to guide us to our hotel (Maps' spoken directions were useful when navigating through Italian roads with Italian signs, while the GPS unit worked better in places without reception). We were already behind schedule, it was getting quite late, and had turned very dark (this part of the island isn't great about roadside illumination).
We arrived at a roundabout, and saw two signs, both pointing to our destination -- we could keep straight, or turn right. The old GPS told us to take a right, which would put us on a course to reach the hotel in an hour and a half. Google Maps, on the other hand, recommended going straight, in a more direct route that would get us there in 40 minutes. We'd had great experience with Google Maps in Sicily so far, and opted to try the route it suggested.
Driving past the roundabout, the road became a bit rougher, but not outside of the norm for the area. We wound around the mountains in the dark, and Maps continued to assure us we were getting nearer to our destination. The first sign of trouble came when we took another right turn, some time later, into a smaller road. We carefully drove around the first pothole. Then came another, and another. The road kept steadily getting rougher, but the car was ok, and we were driving carefully. There were absolutely no lights anywhere to be seen.
After a few minutes on this road, we started following it as it curved left -- and came face to face with reeds taller than the car. Our road vanished into them, turning into an old, rough path that had clearly not been used in years. I got out of the car to look around -- and could see absolutely nothing not illuminated by the headlights. No house lights, no street lights, no sounds except crickets. No cell service. Maps said we were only 15 minutes away from the hotel.
I got back in the car up to turn around, and the car wheels into mud and started spinning. It was at this point that my SO started freaking out. I don't blame her. We managed to, very slowly, turn the car around, drive up over the potholes, and make our way back to that roundabout. This time, we went the other way. Eventually, we reached our hotel, which was pitch dark with no outdoor lighting, had peacocks running around, pictures of Jesus nailed to the room walls, and a deserted wedding banquet hall for a restaurant, but that's a story for another day.
I still wonder where we ended up -- what that road looks like in the light of day.