Quote Originally Posted by popemobile
What about Sicily?

Seems to me like Sicily is in the worst geographical position to conquer anything.
I've had endless bother with Sicily on vh/vh. Just could not get started... wherever you try to expand to you get attacked by superior naval and land armies, inevitably all at once. Had the Byzantines, the Moors, the Venetians and the Germans all at war with me, and no navy to connect Tunisia, Albania, Corsica and Sardinia (the obvious starting provinces to take) to my main two provinces.

Had more luck with Milan (my current game) as the start is made easier by their good cashflow. Once you secure the Italian peninsula plus Venice you're up and running.