Rome/Siena/Florence/Venice

Actually, Italy is very easy to get around. Don't sweat it! Trains between all of these places are easy - though between Siena and Florence a bus might be slightly easier because the bus picks you up at the end of the old town as I recall, whereas the train station is a bit further out. But when I visited Sienna more than ten years ago, there weren't any (or many) direct trains between Siena and Florence - I think there are now.

I think most people would recommend adding your nights to Rome and Venice, actually. I would, given that those are your arrival and departure cities.

I would add one night to Siena, as there are so many hill towns to see, like Montipulciano, San Gimingano, Montalcino, Assisi, I could go on and on! Also, I would add a night to Rome. There is so much to see there. We were there end of May this year; we walked about 12 miles a day, saw so much in three days, but there is so much more to see. You can take a bus, train or taxi, or subway to get around too. My husband and I loved Rome!

You could easily add 2 nights to each of your locations without running out of things to see. If you haven’t been to Venice before, I would add another night there as it’s unique and you only have one full day there (2 nights).

If you mean renting a car just for a couple of days to explore the area around Siena, that's a good idea, but for everything else use public transportation. The bus is the best between Florence and Siena for the reasons Andrew mentioned. For everything else use trains.

Are you flying into Rome and out of Venice? Have you got your flights yet? Look into starting in Venice and ending in Rome. Venice is a magical place to start a trip, and a good place to get over jet lag whereas Rome works better once you are used to being in Italy. Also times of most flights back to North America work better doing it in that direction. If you already have your flights though don't worry, it's not that much of a big deal.

I would add one night to Venice and the other to either Siena or Roma. And if possible add a few more nights total to your trip, there is so much to do in each of the places you are going and if you are doing the long trip from North America you get more bang for your buck (both money and the hassle of the flight) if you stay longer.

Thank you all! I like the idea of flying into Venice and out of Rome so looking into that. We (I!) will only consider renting a car in Siena, I want nothing to do with a car in the larger cities.

Sounds like the trip I'm planning - but in reverse. My wife and I are flying into Venice and then flying out of Rome 2 weeks later. Two days in Venice (probably not enough time but we might return at Christmas), 4 days in Florence (with day trips to Pisa and Lucca), 2 days in Siena, 2 days in Montalcino, 3 days in Rome, and then fly home from Rome. We plan to take the train from Venice to Florence and then rent a car as we're leaving Florence and drive to Siena, to Montalcino, and then Rome. We plan to drop the car off as soon as we get to Rome and rely on public transportation. This is our first trip to Italy.

I would rent the car when I leave Siena.
Siena is full of people during summer and there are also ztl. If you want to discover Romanesque churches in the Sienese countryside or elsewhere in Tuscany. a car would be really nice to have.

Just booked accommodations, yay! Decided on Venice (3), Florence (3); Siena (3) and Rome (4). Now I get to stress about packing! Will be there last week of Sept/first week of Oct.