Itinerary - still trying to figure it out! Suggestions?

You’ll get better advice if you explain what attracts you in these towns. So, in the absence of that info, I’ll give my personal opinions. Of the towns mentioned, my favorite is Orvieto. I’d give it 2 nights (= 1.5 days). It has a a stunning cathedral, a small Etruscan museum, and a couple of other sights you could look into. If you rent a car from Hertz, you can drop it there and take the train to Rome.
Next favorite is Pienza. It’s small, so can be seen in half a day. When we were there, we were able to get a tour of the papal palace through the TI office. Very worthwhile, if it still exists.
Cortona didn’t do much for me. Maybe we had an o.d. of Tuscan hill towns by the time we got there. Because of being on a hill top, it doesn’t seem to me to be a good base for seeing other towns.
Assisi is most important for the Giotto frescoes. If you are not well-versed in medieval/ Renaissance art, you should consider getting a guide for Assisi.

Why stay in Cortona if your objective is a day trip to Assisi/Spello? It is a 2.5 hour drive each way! You would have almost no time to enjoy Cortona with only 2 nights and a long day trip.

If you stay in Assisi three nights you can day trip to Cortona and Orvieto in the same day with less than 4 hours of driving and only stay one place. Assisi is also about 90 minutes drive from Montepulciano. Perhaps you can take a night from Florence, stay 4 nights in Assisi, and make two day trips (Cortona+Orvieto and Montepulciano) plus have a day for Assisi and Spello.

Hi JR, how many are in your party? I am asking because it will affect how fast you can move to the next location. I would hesitate to have a 1-night location, depending on the number of people.

I think as a group you need to decide whether you’re going the Cortona/Assisi route or the Montepulciano/Pienza route. Set realistic plans as a group that you aren’t going to see everything, but all that you do go see should be fully appreciated.

What time of year are you going? Spello has a wonderful Infiorata if your timing is right for it. And Lucca has the Luminara in September where you would want to stay overnight to see it, depending on your date of travel.

How many of you have been to Rome? Two nights there is a very short time.

We originally had three nights in Cortona but car rental there is difficult.

We didn't have any trouble renting a car there a couple of years ago. The rental agency was down off the hilltop. We were going to take a taxi down but someone at the office when the hotel front desk called them for us said they'd drive up in the car to the bus turnabout at the top, then we gave them a ride back. There is parking in lots a little ways down from the hilltop.

However I agree with Laurel. If you want to visit Assisi/Spello then staying closer makes sense. Perugia is much closer and has (or at least had when we were there) car rental right at the train station. Orvieto is only about an hour from Perugia so you could stay there three nites instead of the hassle of changing hotels for a single night. Montepulciano is also about an hour away. We've found Perugia to be a good central base for exploring.

There are three of us and two of us have been to Florence many times and Rome. I have been to Cortona before but the others haven't. Trying to plan something to accommodate everyone is tough. In the past I made decisions, and two of us went with it. This trip takes place mid-October. It has literally kept me up nights trying to figure out the in between days from Florence to Rome. The apartment in Florence is committed to I think. We got an AirbnB and put a deposit down. The apartment in Rome is paid for. So it leaves me with three days to do something in between. I could pass on Cortona. It wouldn't make me sad, but getting to and fro has been a nightmare to say the least. Where else would you base if you wanted to rent a car to see Pienza and Montepulciano? I threw Asissi in when I though we were going to be doing three nights in Cortona. The train says it is 45 minutes on the train from Cortona. That was the only reason I threw that in there. I looked in to a tour to Montepulciano/Pienza from Florence but that makes an awfully long day - like 10-12 hours. So I am back to square one.

We spent a week in Cortona and did a day trip to Pienza and Montepulciano. It wasn’t hard to include them but you have so little time in Cortona. Our appetites were whetted for a stay in Umbria after visiting it from Cortona. Can’t you pick up a rental car when leaving Florence?
Maybe reduce your time in Florence to experience more of Tuscany, not seeing it on day trips?

We split our Florence/Tuscany trip a bit (having arrived in Florence by train). We rented a car upon arrival and stayed in an AirBnB not too far south of town. From there a day trip that included both Sienna and Montepulciano was easy, including time to buy tickets for and do the "Cielo" tour of the cathedral in Sienna).
We also spent a day visiting hill towns like San Gimignano - I imagine a trip to Lucca could also be managed. Dropping the car when we returned to Florence and then walking from our accommodation there was easy. Then a high speed train on to Rome and Naples for us, but I expect something could be arranged for Orvieto. The experts here could help. But Sienna and Montepulciano in a day is not too difficult (on the day we were in Montepulciano, they were filming for the mini-series about the Medici available on some streaming services - season one had Dustin Hoffman - also, if you want the best Florentine steak in Italy, seriously, go to OSTERIA ACQUACHETA while in Montepulchiano).

John, do you remember who you rented from?

do you remember who you rented from?

Unfortunately no.

JR, can you drop a night in Florence and do an overnight in Siena. Rates from there are slightly better or…

Pick up a car in Florence, then drive to Pienza, & onward to Montepulciano. Spend the night in Montepulciano Next day drive to Orvieto drop the car?

https://www.hertz.com/rentacar/reservation/#vehicles

Scroll down to economy Lancia.

The only way I’d do this is by car.
Assuming the Florence and the Rome nights are unchangeable, I’d pick up the car in Florence, drive to Montepulciano/Pienza area and spend two nights there. If you start in the morning, you can easily visit both on the (half) day of arrival.
With two nights there, the next day you have the full day for a day trip. You could visit Cortona, or Assisi+Spello, it is up to you. In the evening come back to your place in Montepulciano or Pienza to enjoy more of the town.
Next morning, on to Orvieto. Less than two hours away. Drop off your bags and visit Orvieto the rest of the day.
You can also drop the car in Orvieto if you rent from Hertz and you are not traveling on weekends when the local Hertz office is closed. If not you can also return the car in Rome at a location that is convenient for you.

I think we will look at getting the car in Florence. And deal with the drop off fee. What's the best place to pick up a car on a Sunday morning outside the ZTL's? I think we will scrap Cortona as suggested and make the trek to Montepulciano/Pienza instead. Will start looking to see what is available. We leave in 3-weeks.

Edit: Well places are pretty booked up in Montepulciano. Will keep looking. We are looking on Hertz car rental and noticed a location at Florence train station. Is that a good place to pick up a car if leaving on a Sunday?

Very detailed directions on exiting Florence here:
https://community.ricksteves.com/travel-forum/italy/florence-car-rental-zlt-zone

The rail station is the only one open Sunday morning, 8-1:00. The three of you should take a taxi there. Are you planning on driving down toward Siena to Pienza & Montepulciano or using the Autostrada? Get accurate directions from hertz as to how to exit the city without encountering ZTLs.

The ZTL is open to all on Sundays, so no worry about that.
If you pick up on a Sunday the only open choice is the new Hertz office on Via Alamanni, a short walk from the station.
Since they moved to this new office from the previous one on Borgo Ognissanti, the directions I provided previously do not apply. Since I don’t know where they keep the cars at the new office I cannot provide a definite update to the directions.
There is an underground garage next to this office between Hertz and the MH Hotel. Assuming that is the one where you pick the car, the only way out of town is to drive along via Alamanni toward the station (no other choice, since it’s a one way street, then as you reach Piazza Stazione turn right onto VIa Santa Caterina da Siena (that is where the bus station is where you pick up the bus to Siena, and then again right onto Via Della Scala, all the way to the end. There are no ZTL cameras on the route, and in any case the ZTL is open on Sunday, however Via Della Scala is a one way street, and toward the end the right lane is a bus only lane, while the left lane is for all. So as you enter Via Della Scala, move to the left lane, because they do have a hidden camera after the church that they use to catch the bus lane violators. Bus lanes are enforced also on Sunday. Since you will be in Florence a few days before renting the car, take the time to walk along the route from Hertz to Via Della Scala. Maybe ask Hertz agents where you pick up the car. I’m willing to bet is the next door underground garage next to the MH hotel but I don’t know.
Regarding the drop off fee, I’ve never been charged for one. I generally rent through www.AutoEurope.com often with different drop off location, and they do warn me that there is a €15 drop off fee to be paid directly to rental office upon returning the car, but I’ve never noticed that charge in my card.

Roberto, thanks for the detailed instructions. If only it were a 15E charge. They are quoting me $100+. Seems excessive, but maybe because I am trying to book from an American site.

Try to see what you can get with www.AutoEurope.com.
I am not sure if the better deal will be with Hertz or Europcar or Avis-Budget, but it is worth a try. Also, if you plan to return the car in Orvieto, Hertz is the only rental there, but I don’t know if AutoEurope works with that office. I know they stopped because of customer complaints about the Orvieto Hertz office. Not a big deal. You can return it in Rome and if you tell me where you stay in Rome, I can tell you the easiest return office to stay away from the Rome ZTL. If you return in Rome you save yourself the hassle of lugging the bags on the train and the cost for an extra day of rental may not be that bad.
$100 for a drop off fee is almost American style gouging, but it is possible that is what they charge nowadays because of vehicle shortage. You are probably more likely pay less of a drop off fee if you return to a major location, like Rome Termini station.

Use the Hertz italy site, and the location Roberto gave you.

While the autostrada route is a few minutes faster, the drive Florence>Seina> Pienza> Montepulciano is very pretty.

So in looking at AutoEurope Picking up a car on Oct. 16 (Sunday) from Florence Downtown Office on Via Borgo Orgnissanti and dropping off at Roma Termini on October 19 for a Compact Automatic Peugeot 308 non deductible is $360.75 with $293.03 due now . The $67.72 drop off fee is included in the 360.75. This is through Europe Car. Returning to Chiusi was about $100 more! Do they normally require payment up front? We will be staying near Trevi area in Rome. Drop off fees for Chiusi was $98.49.

The €67.72 (drop off fee) would be paid locally. You’re paying the remainder for reserving the car, guarantees the price for your dates. As Roberto has said he’s never been charged for a drop off fee.

Will that compact fit all of you and your luggage?

Yes they require payment up front

Christine, I have no idea! I guess we need to look at a bigger car. We all three just have carry on no big bags.

We took a night off from Florence and now have the extra time in the Tuscan Hills. Onward with making arrangements now.

It’s a 5 door hatchback. You shouldn’t have any problems with the 3 of you and luggage.
Note backseat has slight slope, smaller windows
But not uncomfortable unless very tall.

Yes you pay AutoEurope upfront. The amount is fully refundable in case you decide to cancel later (within 48hr from rental date).
The amount you are required to pay to AutoEurope is the cost of the full rental.
The additional amount you quoted ($60 something) is supposedly the one way drop off fee. Every time I rent, I rent a one way rental, it’s rare that I rent and return at the same spot. The drop off fee is something that supposedly you will be paying to Europcar (the actual rental agency) after you drop off the car. Each time I’m told about this drop off fee to pay to Europcar, but I have yet to see it in my credit card, in all these years. I don’t know if Europcar forgets, or if they don’t give a damn, the fact is that in reality I was never charged for it. So take a chance and let us know if you get charged for it after your return.
Regarding the rental vehicle, although you may think you are renting a Peugeot 308, in reality they could give you any vehicle in that class. In the case of Europcar (I’ve rented from them many times), in that category it is almost always a Fiat500L. I guess they have a lot in their fleet. So be ready to get a Fiat500L. Regardless of the model, 3 adults with luggage can easily fit in that class of vehicle. Yes maybe you won’t be able to fit the whole luggage in the trunk (which in the 500L is spacious), but you can fold half of the back seat to increase the cargo space by a lot. If you have concerns about the fact that way luggage will be visible, don’t worry. Even if you get it all inside the cargo chances are Europcar will not have the cargo cover. Half of the cars I rented from them lacked one, so live with it. Just don’t leave the vehicle unattended while luggage is inside. Drop it off at the hotel, then do your roaming around.

I bring this up not as some kind of lecture, but a reminder from someone who got burned. Granted it was all my responsibility, but just a fair warning. If you haven’t previously rented a car in Italy or driven there be very careful with every single aspect of that process, from the detailed rental agreement with very fine print restrictions, to the meaning of every single road sign, and a complete understanding of things like where toll roads are, the turnabouts, speed limits that can change abruptly, and driving restrictions within many of the towns/cities. That country needs money, and I’m convinced numerous mailings of traffic fines mailed to car rental customers is a big part of it.

I’m convinced numerous mailings of traffic fines are sent to those who have numerous violations of traffic laws.

A novel concept

JR - just make sure you do your homework regarding ZTLs, speeding cameras, road signs etc

All drivers must have an IDP which you can get at your local AAA

We have rented cars and driven in Italy multiple times and have never received any sort of ticket.