A reliable option for avoiding currency conversion fees is to open a multi-currency account and get yourself a travel card. Withdraw up to $1,200 per month without being charged ATM usage fees.
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In Italy, cash is still preferred in most restaurants, cafes and other establishments, although credit and debit cards are becoming more widely used throughout Italy and are an increasingly convenient way to pay for things. Visa and Mastercard are widely accepted, although American Express is not.
You don't need to bring any cash. You might want to get 100 Euro from an ATM at the airport when you arrive in Italy and hit ATMs as needed throughout you trip. Consider getting larger sums to avoid the (roughly) $2 ATM fee everytime you use an ATM.
The easiest and cheapest way is to use an ATM at the airport in Rome to get some Euros, although there is usually no need to get Euros before you leave. You can buy Euros in the US but you will pay a premium.
It's always wise to carry a small amount of cash for smaller cafes and restaurants, some public transport options, and taxis who may not accept credit card payments. We once visited the same restaurant 5 years in a row, only to discover each time that their card machine was out of order!