We've always had great luck with AutoEurope. Best prices, good cars, etc. I suggest getting a diesel engine and a stick shift for both great gas mileage and good pickup on the hills. I try to limit my driving within cities because it's crazy. Otherwise, it's like driving in rural USA. Get yourself some good maps of where you'll be driving.
I like AutoEurope as well (they've upgraded us free a few times too). Touring Club Italiano puts out a great series of maps - in my capacity as navigator (the reason why I get to sit up in front!), I've used their maps with great success, as well as another called 'Silver Lining's Best Map of Tuscany' (laminated, easy to read & cultural sights noted on the map). Jerryott gives good advice re driving there. I would also add to exercise caution on blind curves (don't assume cars traveling in the other direction will necessarily be in their appropriate lane at all times, esp on narrow roads). Traveling by car is a wonderful way to see the country & a lot of fun...have a great trip.
Naples driving is a nightmare... not necessarily fast, just traffic jams...
also - the Amalfi coast drive is all hairpin bends all the way once past Sorrento, and the buses come at you on the wrong side of the road because they're too long to get round... you find you have to reverse with the sheer rock on one side of you and a sheer drop to the sea on the other !
Motorways... be alert; if you're driving in the slow lane (really only for slow vehicles and lorries) then watch out for the odd Italian car that's missed its exit ... they like reversing slowly back to the exit road in the slow lane. You're toodling along feeling relatively safe and then find this car hurtling towards you ('am I really driving this fast ?' you ask yourself !) It happened several times when we were over there.
Also - just because you can 'get off' the motorway at one exit, doesn't mean you can get on it again in the same area,if you came off too soon, or too late. Sometimes you have to carry on for several miles in the wrong direction so you can get off where you can turn round....
Public transport is cheap and efficient - coaches are airconditioned... it's much nicer to let the driver take the strain ! Think about it !
Thanks for all your suggestions...we appreciate it.
So...we'd only use it from Milan to Florence and Florence to Naples.
Any sights we shouldn't miss along the way? It's a leisurely drive..stopping wherever our car takes us!
After dozens of fly-drives, I've never experienced problems with roads or other drivers in Italy, and love driving there. I'd recommend using a car between cities to access smaller country places, (and if you can get the 'Rough Guides' series in US, I'd recommend them to find smaller places), but I'd turn the car in when you get to a bigger city. Hertz are a few pennies dearer but we always use them, a they don't charge any more for 'open jaw' hires, (dropping off somewhere other than where you pick up) and have lots of town centre and airport centres. Book the smallest cheapest 3-door car (they almost always upgrade you to a 5-door)which at 30 Euros a day is cheaper than taking a taxi to the airport. And finally, look at www.michelin.com for great maps, routes and accurate travel times
sorry- I meant www.viamichelin.com