Itinerary Check for Florence/Hill Towns

You can do Siena on a day trip from Florence.

As for Orvieto and Assisi, you left out Perugia, which is near Assisi. We are planning to spend a week or more in Umbria in the future. Consider skipping Cinque Terre this time and spend two more nights in Umbria. You will not waste so much time on travel.

I would take the train. If you haven't read on this forum about the plethora of tickets that drives pick up in Italy, do so. One person was ticketed for going two KPH over the speed limit.

To avoid so many 1 and 2 night stays in such a short time, and since you have already been to Rome and Venice, think about skipping both for this trip and instead fly in and out of Florence. You could make your bases just Florence and Siena (both Orvieto and Assisi are an hour and a half drive from Siena), or, if you really want to go to the Cinque Terre, your could stay in just Florence and a town there.

To save money, you could also fly in and out of Rome, traveling by train to Florence or to Orvieto right away, without a first night in Rome. Returning to Rome for a night before your flight home.

September will still be quite hot and is really not the "shoulder season" that it was many years ago --- we once stayed in Florence for the whole month of September plus a bit of August and the first week in October and saw no difference in tourist crowds (or heat) until just before we departed. Same with visiting the Veneto in September this year. Still, Italy with heat and crowds is still much better than no Italy! But September would make me even less inclined to choose 1 and 2 night stays and to spend so much time in transportation (and packing and unpacking and finding your accommodations).

One person was ticketed for going two KPH over the speed limit.

Please, do not give wrong info to current and future readers. Internets forums are meant for the opposite.
There is a leeway of 5 kph or 5% of the posted limit, depending on what's best for the offender. So nobody has ever been fined for going 2 kph over the limit and keeping on repeating it won't make it true.

Is it wise to drive from Rome until Florence, and then take trains?

Now that we cleared away internet nonsense, the wisdom of driving comes down to a few factors:

1. Can you memorize the ZTL sign and "see" it when approaching an historic center? If not, park in the outskirts "out of the walls" and walk. Or take the train.
2. Is there a real reason to drive when high speed trains run at 250 kph between Venice, Florence and Rome? More, There are many trains a day from Florence to Siena and from Rome to Orvieto. As an example, Is there a village along the road that you absolutely want to visit? A cute little hill town not served by trains?
3. Can you memorize the translation of a sign saying "Controllo elettronico della velocità"? It means "There may be a Speed trap ahead".
4. Both Trenitalia.com and Italotreno.it sell Discounted train tickets For advance purchases. These tickets are often cheaper than one day of rental plus gas, tolls and parking costs. Unfortunately they also come with restrictions about changes and refunds. What's more important for you, money or flexibility?

Is there any benefit to reversing this trip?

I think that flights to US from Venice depart very early in the morning and the direct water bus to the airport takes ages. In Rome there is a 32 minutes train to FCO airport.

I would definitely agree that you should fly into and out of Florence thereby eliminating the travel day from Rome and to Venice. My personal preference is to settle into only 1 or 2 cities and make day trips from those bases. You can easily visit Orvieto and Assisi from Siena or Florence by car, bus or train and you might want to add Montepulciano (my personal favorite hill town). I would recommend focusing on Tuscany and Umbria and save Cinque Terre for another trip but two nights there would be lovely (though VERY crowded in September).
In terms of transportation, the bus and rail systems in Italy are excellent, easy to use and much less expensive and less stressful than renting a car.

Having just returned from 3 months in Italy I can concur that September is no longer the "shoulder". It is still very crowded. If you can move your trip to October it will be less crowded and the temperatures will be better.

I suggest limiting or eliminating the one-night stands. Just too much time wasted with packing up, checking in, etc. My answers to your questions:

Question: Should we drop Assisi or Orvieto? And/or just stay 1 night in Siena? If you fly into Rome, go straight to Orvieto upon arrival and spend maybe two nights there if you want a full day there (which I suggest). You can either do a day trip to Siena from Florence or spend one night. I've done the day trip, but spending a night would give you more time there.

Question: Is it wise to drive from Rome until Florence, and then take trains? I suggest taking trains whenever possible unless you just can't get to a destination without a car.

Question: Is there any benefit to reversing this trip? We don't have our plane tickets yet. Yes, if you plan to go to Venice since departing flights leave there very early. Since you've been before, perhaps skip Venice and concentrate on the other cities.

My other thoughts - if you skip Venice and still go to Cinque Terre, and if CT is your last stop, you could consider flying into Rome and home from Milan. Might be cheaper. Re: Florence, I personally think 2 nights is not enough, especially if you're doing a day trip from there. But, I realize you have limited time. I'd drop Assisi if it meant more time in Florence.
Have a great time, sounds like a wonderful anniversary trip!

Rick's itineraries are way, way too fast for me. A whole string of 1-night and 2-night stops would be miserable for me. One night just gives you hours at that destination. There's nothing wrong with your destinations (except possibly Cinque Terre, due to horrendous crowding); you just have way too many of them and are probably not going to have time to appreciate them.

I would not travel across Italy for one night in Venice (which I love), even if it were not often difficult to fly home from. I agree with Kathy H. that flying home from Milan should be considered. Florence (or Pisa) would be fine if convenient to where you ultimately decide to end your trip, but from some origins (including mine) it would typically be a lot more expensive than flying out of Milan or Rome--as would Venice.

Oof, Amanda, you have a lot of packing, unpacking, checking in and out and moving around in this itinerary! With somewhat limited time to work with (10 nights IF you don't have to cut 1-2 of them?) I'd cut it to just three locations and day-trip from Florence

Flying in and out of Florence would certainly be optimal but prices may be higher than you want to pay, and you might find more workable itineraries in and or out of Rome. If flying into Fiumicino, I like the suggestion of going (train) directly to Orvieto and spending two nights there. Then two nights in the CT (train) followed by 5 nights (train) in Florence with day trips (Siena, Lucca, Fiesole, Pisa are all easy choices via public transit) from there. Then spend 1 last celebratory night in Rome prior to flying home. This trims at least 1 location (Venice) you've seen before, although it drops Assisi as well.

If you have to cut the itinerary by 1-2 nights, then (sadly) Florence and some of those day trips would have to go UNLESS you can manage either flights both in and out of Firenze or at least out of there. One question? How important is the C.T. to you and your DH?

Great tips everyone! I think we will definitely try to fly out of Florence or Milan and not go all the way to Venice. Also I think we can move to October so that will help with crowds. We'll skip the driving too and just do trains. Unfortunately we don't have time to take stops to little towns anyway on this trip. I really appreciate the help!