Right, this itinerary really stumped me and I skipped it. However, I couldn't ignore it forever and decided to get down and try and do it. I went for the word.
The word is 'quixotic'. Not an easy word to play with. The others in the category weren't easy either. After messing around for a bit, I stumbled upon this particular image and then everything came about together. So here's my effort:
Itinerary #6: Quixotic