Auto Europe is offering a fantastically priced deal to Italy that bundles together airfare and a rental car. (Just go to the site and click on "Specials.")
Rates start at $557 per person for round-trip airfare and three days with a rental car to fly into Florence or Venice from Boston or New York ($619 from Miami or Chicago). $557 is also the price from Boston to Milan; for some odd reason, the price jumps to $579 for flights to Rome from New York and Boston, $647 for flights to Rome from Miami and Chicago.
Those are the prices for winter travel (Dec. 26, 2008 to Mar. 31, 2009; rates go up by more than 50% in spring), and don't include fuel surcharges of $264 to $330 (other government fees, taxes, and surcharges can add up to an additional $195.)
By the way, three days with a car is perfect for a trip of a week or two. Figure you'd be better off getting around by train to link the big cities, and rally only need a car for exploring hilltowns and vineyards and such. So on a typical 8-day trip (leave Friday night, return the following Sunday), you could fly to Rome, spend three days there, then take the train to Florence and spend two days there, then pick up your rental car to spend the last three days driving back through the hilltowns of Tuscany and Umbria on your way to Rome's airport to depart. Perfect.
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