What the heck?!

Could someone explain this to me? And would someone help me Fisk the s*** out of it. I have class now and can’t do it myself. Trust me, this one is begging to be mocked and taken apart. Its so ridiculous!

Dumbest line in second paragraph:

He had been to the Eternal City in the past, but this trip was different. Instead of spending his days wandering the city�s ancient streets in search of unique shops and hidden restaurants…

He’s a history professor!!! Surely he could do something more profound than eat and shop! Agghhh!!