More likely than not I can beat YOU to one of the two settlements in Siciliy.
That'd be a fun bet to take

Seriously, the game mechanics are truly abysmal concerning sieges (which is the only way to get walled cities like Syracuse and Corinth). If you were in command of a Roman army with a handful of light Hastati infantry and Velites skirmishers, I dare say you'd get your head handed to you, literally, if you tried to siege cities of that size.

Another area where the designers chose to ignore some basic rules of engagement...here, concerning the size an army needs to be to siege a city. [end of rant].