Maybe my problem with Palermo was that I felt unsure of the scale/proportions of the place. A general rule of thumb I try to follow when in new places is to find the highest spot I can in order to get a lay of the land. Going to Monreale allowed me to do that and get a better handle of the Sicilian landscape. The cathedral itself was also amazing. The thing that struck me was the relative age of it. The building was completed in 1182, 150 years before the building of Notre Dame. Obviously Monreale is not on the same scale, but the ability to build such a grand building at that time tells you something about the wealth of Sicily.
From there, it was a slow but breathtaking trip to Segesta. Carmelo, our bus driver, took us through some small Sicilian towns and rocky hills. Our big bus could barely fit on the road a lot of the time. The great thing about Segesta (and a lot of other places that we went to) was that there was nearly nobody else there. We were free to explore the Greek temple and Roman theater without being surrounded by other tourists. In the theater, my group had the opportunity to recap the first four books of the Aeneid to our classmates sitting up high. Segesta is where the Athenians sent envoys to before their Sicilian Expedition. On the site of the Roman theater that we were in was an older Greek theater that the Athenians might have been in while they listened to the Segestans make their argument for an alliance. It was special to be able to perform for my classmates in a thousands year old theater. Now that we are out of Palermo, things, at least for me, are really starting to get interesting.