Great post Hersh. Navigation in an unfamiliar environment scares me sh*t out of me too! I'm fine on the radio, sometimes I'm so keen I even read back more than I need to!
I try to always find routes where easy to identify lakes, large towns (not stupid 2-pub, 1 house type towns) etc are located. I always backup the visual nav with VORs/GPS. I feel navigation is sometimes very poorly taught. So much emphasis is on being *exactly* on track that one devotes too much time to worrying about minor things. I remember during my training I found it difficult to identify towns 10nm away working hard on the DI and wasting time on maths formulas. If I now glance at a chart, pick a rough heading and I seem to always arrive at the right place (even w/o GPS!).
I still get nervous flying to airports for the first time, but I guess that goes with being low hours.
p.s. Hersham, I'm sure you'll do fine on the Checkride, I passed (I made a BIG mistake I'm too embarrassed to repeat here!!)