I've just finished reading Machiavelli's The Prince and now I'd like to watch some nice documentaries (or any media really) about Italy around the time the book is concerned with. Things about the Borgias or the Medicis would be good.
Cheers!
The Prince is a very complex text, more than its short length and popularity would imply. One of the best introductions which contextualises the book against both other texts written by Machiavelli but also his historical and social milieu is Quentin Skinner's Machiavelli: A Very Short Introduction (19&1). The exploration of both Machiavelli's society and concepts is fantastic. It's also available for basically nothing except postage second-hand on Amazon!
I would definitely recommend "The Medici - Godfather of the Renaissance" It talks about the Medici, the Renaissance and also Machiavelli. Link to the first part on Youtube: https://www.youtube.com/watch?v=GOAVRcI6mFU