Rome
City Film: A movie to associate with Rome, La Dolce Vita (1960) of course! But that is summer, so here's a winter tip:
What to See: Ancient Rome and its incredible iconic structures, especially if there is snow.
Where to Stay:
Hotel d'Inghilterra - 14 via Bocca di Leone
Milan
City Film: We can't but help imagine Milan as portrayed in the opening wintery scenes of the film, I Am Love (2010).
What to See:
The newly restored Galleria Vittorio Emanuelle II. This glass-roofed iconic structure is filled with elegant shops and a few cafes. Right next door is the Duomo.
Where to Stay:
Hotel Armani - via Manzoni 31
Hotel Bulgari - via Privata Fratelli Gabba, 7b
Venice
City Film: Casino Royale (2006) we love it, and it shows off the city to spectacular effect, but on a more intimate level try Brideshead Revisited, (2008).
What to See:
Carnevale should be in full swing (January 23rd - February 1st). This is also the season of the Acqua Alta (high water), so be prepared to walk on the city's other type of famous bridges, those elevated wooded paths which will to keep your feet dry.
Where to Stay:
Danieli - Sestiere Castello 4196
Florence
City Film: The iconic A Room with a View (1985) and the terrifying Hannibal (2001).
What to See:
It's cold in Florence in the winter (Wow, thanks, Red Maps, big surprise!) so take the opportunity without the summer crowds to see the Uffici and Accademia Museums.
Where to Stay:
Lungarno Suites - Vicolo dell'Oro, 6r
See Red Maps set of 4 Italian city guides: La Dolce Vita