First trip to Italy

The only place a car would be useful for your desired destinations would be Tuscany. Elsewhere it would be a costly burden and worry, particularly inside Florence and its dreaded zone a traffico limitato (ZTL) - restricted traffic zones that are monitored by automated traffic cameras from which there is no escape. I think it's generally best to travel in a straight line as much as possible, to avoid costly backtracking (both time and money). So, fly into Venice, then take the train to Florence, then rent a car and explore Tuscany and drop off the car as you get to Rome, and fly out of Rome. Hopefully Roberto will come along to chime in. He's the expert. And be sure to check out this fantastically helpful site: http://www.roninrome.com/

William, my wife and daughter are doing exactly the same thing only they will skip Milan. They will be traveling in the same time frame. They will arrive by plane in Venice and depart by plane from Rome-FCO. You could do the reverse. I have their complete itinerary in an Excel spreadsheet. If you want it, send me a PM with your email address and I'll send it to you.

William, you will really benefit from buying Rick's book on Italy. I can't stress that strongly enough. His books are especially useful for American first time travelers to Europe. Not only does he have suggested itineraries (a bit too hurried, IMHO), but he also answers questions you don't even know you should be asking. For example, he talks about how it's often best to fly into one city and out of another, so you might start in Rome and leave from Milan. And you have a very short time frame to do all your planning if you're talking about this Sept/Oct. Get moving! Happy travels.

With two weeks, do Rome, Florence/Tuscany and Venice. Leave Milan off the agenda. IMHO it is the last city I would ever return to, and wouldn't have missed anything by not seeing it. The history, culture and beauty are in the other cities. If you have a big wallet and your wife is a fashionista, she can do all the high-end shopping she wants in Rome near the Spanish Steps.
(Keep in mind that I've been to Milan several times, since we have family near there.) Agree with the poster that you may want to do an open-jaw flight. You could fly into Rome and depart from Venice or vice versa. This will save both money and time. As for time, I'd give Rome 5 days, Florence/Tuscany 4 (including side trips from Florence) and Venice 3. If you have an additional day, add it to Rome, there's so much to see you could spend the entire trip there. DO get the Rick Italy book. If you sleep in Florence, the public transportation is so good that you won't really need to rent a car to do your day trips to Siena, Sam Gimigiano, etc. You can also book a wine tour out of Florence that will get you into the countryside, and you won't need to rent a car.

Personally I love Milano but I agree with Donna that it's the place to drop from your itinerary. If you can fly into Venice and out of Rome, you won't have to backtrack. Venice-Florence-Tuscany-Rome. If you plan to drive at all, be careful of where you park - yesterday a couple staying at the same B&B as I was had their car towed, because they didn't notice that the piazza they parked in was not the one the B&B owner told them to go to, and there was a Thursday morning market...and an expensive vacation day spent on car retrieval.

I agree with Donna. Venice 3, Rome 5. Start in Venice, end in Rome. Venice is easy to enjoy while recovering from jetlag. Wander the streets, ride the vaporettos and enjoy the scenery, soak up the atmosphere. If you really like Renaissance art and architecture, 3 days in Florence is a minimum. Then day trip to Siena and San Gimignano. Otherwise, one day is all you need. Stay somewhere else, use a car to visit little towns in Tuscany and see Florence as a day trip (and be careful where you drive in Florence).

I second my predecessors. Arrive VCE depart FCO. I wouldnt do the reverse. FCO is easier and faster to get to from Rome city center in the morn of departure back to US. Not so to VCE from Venice city center. VE > FI(Tuscany) > RM is a Classic for first timers.

You're getting great advice here. We're just back from eight weeks in Italy and never felt the need of a car. You might want to add a day to Venice simply to allow for a day of jet lag and maybe do a day trip to Padova or Ravenna from Venice. I highly recommend the new Italo train that runs from Venice to Florence SMN. They have been running some great online specials that give you a first class ticket (they call it Prima) for less than a second class seat on Trenitalia. From Florence you can take a day trip to Siena via the Sita busmake sure to take the rapida as the diretta ironically isn't actually very direct LOL and take quite a bit longer. There are a lot of great wine country trips you can book out of Florence. Then take the train into Rome.

I agree, drop Milan and spend more time in Venice as advised. You will have jet lag and you will need to adjust. You will want to see Venice and need the time there taking into consideration the jet lag. Look at the Italy tours and the Rome tour as you will be able to gage how much time you need and what you will want to see. The tours give excellent ideas as to what there is to see in Italy.
I have been on the Florence and Rome tours and they are a week each and it was just enough time to see most things. Again, I agree definitely buy the RS Italy guide book and bring it with you to Italy. It is a wealth of information. Also don't forget to make museum reservations in some of the museums and the guide book will tell you which museums and what there is to see in the museums. You don't need a car. Florence and Venice is great as you can walk every where for the most part. And of course Rome is larger but a city where you walk and take the subway and bus and taxi if you need to. Having a car in Rome is a not a good idea at all. Romans drive fast and parking is a headache. And really you just need to be able to walk. Two weeks is excellent time fram as is Sept/October. Seeing the three cities will be spent well in two weeks and going to Tuscany for a few days is great. Remember flying in and out will cut down on your time for being in each area as well as traveling from each city and getting to the hotels. Spend the least time in Venice, more time in Florence and the most time in Rome. You really need to read up on what you want to see to determine how much time you think you would like to stay in each city and in Tuscany. Have a great trip.

We started in Milan, spent 1 night and say the Duomo and The last Supper. Then we were off to Florence for 3 nights. Siena was next, spent 2 nights. then Assisi, spending 2 nights. We stayed in Rome for 4 nights. And yes, we back tracked to Venice, stayed 3 nights, and flew back from there to the states. So I disagree with the others to skip Milan. I found the 1 night there, my first day in Italy, was perfect to see the few sights we did. Back tracking to Venice from ROme was also not bad, it only took a couple of hours. THe reason why we did it the way we did was it was way more expensive fly into and out of Rome. We found an incredible deal flying into and out of the cities we did.

I've been planning my trip to Italy for weeks and I am sooo glad I came across with this website because I was planning to stay a couple of days in Milan. Thanks to you guys I've decided to spend more time between Florence and Roma.