Tuscany drive

If you are comfortable with the driving you could pick up car in Rome and head to Tuscany

Most agencies will close 12ish til 4 ish
The agencies at Termini may be open all day as will the airport locations

Or do Florence first. Pick up car for Tuscany as you leave Florence then drop off at Florence train station location and hop on train to Venice.
( Simplest, probably cheapest)

Here’s info about getting in/out of Florence-thank to Roberto:
https://community.ricksteves.com/travel-forum/italy/picking-up-a-car-in-florence-to-drive-thru-tuscany

Also note: Florence is IN Tuscany ;)

If you plan to spend time in the province of Siena, as many tourists like to do, it makes more sense to rent the car in Rome, rather than spend the money and time to go to Florence, then backtrack to the province of Siena which is in the middle between Florence and Rome (about 2+ hours north of Rome and 1.5 hours south of Florence).

If you want to minimize driving, you can also rent a car in Orvieto (Hertz only) or in Chiusi (Avis-Budget only). Both can be reached from Rome via train. They are small franchise offices, so they observe limited opening hours on Saturdays (morning only), they are closed on Sundays, and they observe a couple of hours closure at around lunch time. Personally I would rent in Rome and drive from there. Then if you plan to see Florence for a few days before going to Venice, return the car in Florence as soon as you arrive in Florence (a car is not needed or advised in Florence).

You need to do a lot of further research. Is your itinerary still the same you posted on another thread?

The first thing I'd check is what surcharge rental companies charge to pick up a car in one destination and return it in another. There may be little or none, or it may be more substantial. Also, since you will be there in peak season, many agriturismos (villas) have a minimum stay requirement. You should have your plans pretty firmed up before leaving home.

Depending on the day of the week, I suggest an alternate plan. Train from Rome to Orvieto. Spend the evening and night in Orvieto and pick up the car in the morning. Then. determine what part of the Tuscan countryside you'd like to stay. You can stay south, like Montepulciano or north, like San Gimignano/Volterra. Either would be fine, but choose one. From either, turn in your car in Florence or Siena and go from there.

How many days do you plan to spend in Tuscany? I really don't see any time allotted. Given what I'm seeing, I suggest going straight to Siena and do day trips from there. If you are going to spend just a day or so, don't bother renting a car.

Looking at your other post, I don't think you have a realistic plan overall. I agree with those on the other post who believe you are moving from one place to another way too frequently. Based on years of traveling throughout Europe, we spend a minimum of three nights in one accommodation. That gives you two full days in a location. On our last trip to Austria and Slovenia in December, we spent 12 days in 3 locations and that seemed rushed.

Do you have reservations in all the places you've listed? When is your trip? You said Summer, but there's a big difference in making arrangements if you are going in June compared to August.

As you Can see I have not finalized my plans. I’m going in a few weeks. I have accomadations for all scenarios, now I’m just trying to find the best one so I can cancel things. As of now I have 3 nights in sorrento, 1 night in capri(nights 1-4) then move onto Rome from capri. 3 nights in Rome (night 5, 6, 7)see Vatican in morning and go to Siena. I can stay 2 nights in Siena and use it as my base as I explore Tuscany or stay somewhere else for those 2 nights (night 8, 9). 3 nights in Florence (night 10, 11, 12) and then 2 last nights in Venice before we go home. I realize it’s a lot of moving but the driving part from Rome to Tuscany and exporing is a lot of the stuff we love to do. Flight into Naples and out of Venice can not be changed. Is Siena a good spot to do a day of driving and exploring?

We just returned from a trip which included three nights in Siena , three nights in Pienza, and three nights in Florence. From Siena we day-tripped one day to various Chianti villages. The other day we day-tripped to Volterra (good museum) and Monteriggioni. We stopped at San Gimignano the day we drove from Pienza to the Florence airport. Neither of us liked San Gimignano. Most of those 14 towers are not visible while in the town which is extremely crowded (almost to the level of Venice or Florence). Unless you are very lucky, parking is a long slog from the town. My husband described the town as a medieval shopping mall.

From Pienza we also did two day trips. One day we drove around the beautiful green Tuscan country side, stopping at a few of the little towns. The other day (rainy) we drove to Cortona which has an excellent Etruscan museum and some higher-quality shops, then stopped briefly at Lake Trasimeno on the return back to Pienza.

The day we changed hotels from Siena to Pienza we dropped our bags at our Pienza Hotel (Hotel San Gregorio which I highly recommend) then drove to Civita Bagnoreggio. Interesting place to visit but do not attempt it if you aren't up for walking about a mile of steep downhill AND uphill. The bridge feels safe but it spans a very steep gorge which might bother anyone with a fear of heights.

I’d drop that 1 night in Capri

Your transit from there to Roo will take most of the day so you’ve left yourself with only 2 full days in Rome

Capri
Ferry to Naples
Taxi to train
Train to Rome
Taxi to hotel?
Ugh that’s a full day travel
I doubt it’s worth it for 1 night

I don’t see how you can day trip from Siena when you are arriving late in day and have just that next full day unless you don’t need to see much of Siena? In that case why are you there?

As you Can see I have not finalized my plans. I’m going in a few weeks. I realize it’s a lot of moving but the driving part from Rome to Tuscany and exploring is a lot of the stuff we love to do. Is Siena a good spot to do a day of driving and exploring?

Have you been to Europe, especially Italy before?

Siena would be a good base to explore. You only have one day for the Tuscan countryside? If so, I'd head towards San Gimignano and Volterra. You can fit that in one day if you leave early and stay late. Remember you need an International Driver's Permit (IDP). You can get one at AAA. Also study up on the Italian rules of the road, especially ZTLs. Almost all towns in Tuscany have a ZTL where you cannot drive. They are well marked, but fines for infractions are expensive.

Remember 2 nights = one day. I'm concerned that the trip is soon and you haven't finalized your plans, especially since you'll be there in the middle of tourist season.

If I went to capri for 2 nights and then sorrento for 3 nights can I get train straight to Rome. This is so overwhelming.
Night 1,2 Capri
Night 3,4,5 Sorrento or amalfi town (which one?) How long from Rome to Sorrento is it still a full day?
Night 6,7,8 Rome
Night 9, 10 Sienna area
Night 11, 12, Florence
Night 13,14
I see what you mean. Its too much traveling. Maybe I should go straight to florence set up shop and take a day or 2 exploring sienna area. Is that feasible?

Night 3,4,5 Sorrento or amalfi town (which one?)

In April I spent 3 nights in Sorrento, 3 in Capri and then 2 in Amalfi. The two full days in Sorrento I went to the AC by van one day and boat tour the other. I really wish I had spent those 3 Sorrento days in Amalfi. To me, hands down the best way to see the AC is being based in the AC, not based in Sorrento. The towns are nicer in the morning, the late afternoon and evenings without so many day trippers. They are still pretty full, but not as much. Also, by being based in Amalfi you spend a lot more time in the AC instead of Sorrento and you save time going back and forth from Sorrento to the AC.

From Amalfi to Rome would take about 4 hours, first the bus to Salerno and then the train to Rome.

Which amalfi town would you recommend?

Which amalfi town would you recommend?

I would stay in Amalfi (town). It's easy to get on the buses and ferries from there. Staying in another AC town seems to add some complexity to moving around the coast.