|Route 66, USA|
Some famous trails/ travel routes to check out:
-The Gringo Trail - South America
-The Hippie Trail - Asia
-The Banana Pancake Trail - Asia
-The Silk Route - Asia
-The classic Cape to Cairo route - Africa
-Route 66 - USA
Try adapt them, incorporate sections in your 'own route'.
Some routes my be closed because of war and may have to be
done in a roundabout way.