To Rent a Car or Not to Rent a Car (in Tuscay) - that is the question!

A car gives you maximum flexiblity. You don't need one in Siena but if you want to see towns like San Gimignano, Volterra, Certaldo, or others the yes, get one. Driving in Italy is no big deal as long as you aren't in a city.

Check with your jotel to find parking. Drop it in La Spezia and train. Or, train from Siena to 5 Terre.

Car is good idea for touring Val D' Orcia and rest of Tuscany countryside for a couple of days so yes would rent a car but only if you are not doing that bus tour since it seems similar just without you doing the driving.

Not sure if where you are staying in Siena has parking, if not it may not make sense to pay to keep it parked the whole time outside of town down the hill. The Siena parking aspect is probably your biggest hurdle to figure out.
Since renting in Siena either return there or drive your rental car to La Spieza a few hours away to return the car and take the train there to Cinque Terre.

Most of the hill towns will have lots right outside of town for parking some will be pay, others free depending on the size of the town. Don't drive through any walls and you that one rule should keep you from any ZTL concerns.

Driving around is easy enough, renting is easy I do think a GPS is borderline required though but as long as you have data or rent a wifi hotspot you only need your Phone to have GPS. I used the Waze APP which is free on an Iphone and that worked perfectly for the regions in question.

Definitely would not want a car while in the Cinque Terre and would probably prefer to drop it off before La Spieza as that is a long drive and will be all highway, so not really scenic at all.

Siena has car rental companies. I ran into an issue renting there because they are closed on Sunday and open half a day Saturday. So I ended up renting at the Florence Airport where they are open all Saturday and Sunday. There is a car rental option in Florence as well. You would exit out of Florence on a one way street so for that part no ztl issue. For returning the car you would need to get instructions from them re the ZTL issue to return the car. We are using Kimwel which is a car rental wholesaler based in the US. They primarily use Avis but do deal with other car rental companies. Our trip is the end of April, Venice 5 days, Siena 6 days, Rome 2 days.
We always short ourselves on Rome. One trip we will spend a few days there, but for now we always have something new to see when going back.
Now for the next thing to work out if you do rent a car; parking. If you have already booked your accommodations in Siena, email them re parking and see if they have arrangements available. My accommodation contracts with a parking valet service and charges 25 euros a day for it, a small break on the daily parking rate. If you don't have an accommodation yet you could select from the ones that offer this. Or you might find an agritourismo close to Siena, there are some that are very near the city. You could look at www.tripadvisor.com for hotel, b and b or agritourismo reviews and /or booking.com.

I like slow travel for planning hill town visits and driving around the area, such as the Val d'Orcia, though their other options.. http://www.slowtrav.com/

Definitely have a car while in Siena (or Siena area) then drop it off in La Spezia (near Cinque Terre).

Siena is a good central base, however the historical city center is forbidden to car, therefore you need to select a hotel that is either located outside the historical center and preferably with in premises parking. If the hotel is inside the historical center you would need to park outside the center in a parking lot or garage, then walk to the hotel. Some hotels can provide temporary access (they enter your car info in the city website) for you to drop off your bags, but only for the time necessary for the check in. Contact the hotel for details, but my first choice would be a hotel outside the Limited Traffic Zone or even out of Siena altogether.

With the car, you have no reason to book a tour. You can do your own tour.

Most popular day trips from Siena (besides Siena, which you would do on foot):
San Gimignano,
Volterra
Chianti Hills
Monteriggioni
Pienza
Montepulciano
Montalcino
There are many more, but you can only do a couple towns a day.

Parking is generally available around the historical center (often inside the ancient city walls) of every town.

I presume Firenze (Florence) is not part of this trip (maybe visited previously). If Florence is part of the picture, the best parking from Siena is at Parcheggio Oltrarno, near Piazzale di Porta Romana.

When I was in Siena (in 2009), I rented a car for two days and took two separate trips around the area.

I got GPS, and I was very glad to have it since I was traveling solo. If you have a passenger who is a good navigator, you might not need it, but even though I studied maps very carefully, I would have been completely lost without it, just getting in and out of the city.

I found free parking in Siena for the one overnight I had the car. There is a parking lot and also street parking along Viale Vittorio Veneto.

The first day with the car I drove south and visited Montalcino, Pienza, and other towns in that vicinity. I especially enjoyed stopping in Bagno Vignoni and at Sant'Antimo Abbey. The second day I headed northwest to Monteriggioni, Volterra, and San Gimignano. I enjoyed all the stops, though by the end of the second day, when I hit San Gimignano and found horrendous crowds and tacky souvenir shops, I was less enchanted than when I started out.

re parking in Siena,

the place we will be staying at offers a valet service. Must be a very rare offering so I thought I might review it. I re read our information from them and they have private parking outside the historical center, comes with valet service. We arrive first at the private parking area, then their service provider brings us into the historical center to the hotel, unloads our bags for us and they then drive our car to the private parking area. Then they return the car to us when we are leaving, such as for a day trip. There are several options for parking such as parking the car ourselves and walking in. What I like is that they have a parking program with several options for their guests. I gather this is not common.

Driving a car in Italy to visit the villages will give you so much flexibility. We have rented numerous times in Europe, and especially to savor the Tuscany/Umbria areas. The unease one feels because they have not driven in Europe might outweigh the freedom you get !

One idea may be to stay at Frances Lodge outside of Siena. You can walk into the town and still have a safe, easy location to keep your car.

unless you like hiking or bicycling in Tuscany ... you need a car.

We have stayed at two Siena hotels that had on site parking when we were there Palazzo Ravizza and Athena -- I don't know if it has changed since then -- but I'd rather have my car and a ZTL permit than valet service.

Thank you for the information! We do have a hotel booked already and it sounds like our hotel has private parking for 15 Euros a day...contacting them today to reserve. I do understand all the rules of not driving in historical towns. We've been to Florence twice, so not going there this time around. I am in sales & travel quite a bit, so even in the US I always use a GPS....will definitely have one.

PLEASE VOTE on these itineraries and I'll start firming up my plans!! Pretend cost doesn't matter, ideally what would be the best & easiest way to navigate this portion of our trip?

Rent in Rome - drive to Siena - keep car for 2 days - return in Siena - train to CT?
Rent in Rome - drive to Siena - keep car all 5 days - drive to LaSpezia?
Bus from Rome to Siena - Rent car in Siena - keep for 2-3 days - return car in Siena - Train to CT?

Definitely no. 2 option is the most logical.
Pick up rental in Rome, return rental in La Spezia.
You will need the car every single day, except for while visiting Siena itself (a day at most).

Analyze and select rental options in:
www.autoeurope.com
www.kemwel.com
(both part of same corporate umbrella, but check pricing of both)

Driving in Tuscany is not difficult. Most of your travels to small villages are however on narrow 2 lane highways that may be very curvy.

You probably don't have much of that in the proximity of Cleveland, but you can test your skills by spending a weekend driving in the Allegheny National Forest or the Susquehannock State Forest in Pennsylvania.

I know I live in Cleveland but, have driven many times in Hocking Hills, OH & have spent many summers driving in the mountains of West Virginia. I'm not at all nervous about the driving portion. I do appreciate the heads up!! Just want advice on the logistics of picking up cars & dropping off & routes vs. trains, etc. It looks like taking a train from Siena to CT requires changes & takes longer than driving. So, thinking of Option 2 as suggested.......any other opinions or tips about picking up at Rome's airport and dropping off in LaSpezia? I know there are different drop offs.

I vote for option 2 because your plan does not include any time in Florence this trip. It allows you to drive directly to Siena, bypassing Florence. It also would allow you to stop along the way in the Val d'Orcia. In our case we arrive by train from Venice so we are stopping off in Florence for some leather shopping before heading to Siena. Have family in Bay Village, best roller coaster ride I ever had was near by.

ttmom12 -- THAT would be at Cedar Point! One of the Best Roller Coaster parks in the world!! Thanks for your opinion! I think that's what we'll go with. We have been to Florence twice.....never got to Siena either time because it was always during the Palio and we just weren't into that. Looked at the driving time and it saves a lot of time over train.

Now, I have 3 months to find someone to tech me manual transmission!! Actually, looking forward to that! And, I know to get a IDP......

Thanks for the help......I think I just needed someone to tell me it's good to have a car this time around. We've been all over Europe but have never needed a car. We're really good at trains, buses & walking! Now, onto car rentals!

Driving a stick- Its actually fun once you get the hang of it. Go for it! I learned to drive a stick on my husbands Tr6 along time ago, though I don't drive one now.

You don't need to go all the way to the Rome Fiumicino airport to get the car if you are already in Rome.
I don't know where you are staying in Rome, but the rental locations at the Tiburtina train station are very close to the TANGENZIALE EST / A24 freeway. Once you get on that elevated divided expressway just follow the directions to the A1 to FIRENZE (Florence). All rental companies have an office at or near the Tiburtina station.

The signs to the freeways are green and will say AUTOSTRADE (freeways).

This is the ramp to the Tangenziale Est near Tiburtina. Another photo here

Once on the Tangenziale Est/A24 follow the directions to FIRENZE through the GRA (Grand Ring Beltway) as displayed in the signs in this photo.

Even if you get the wrong turn, you can always get back on track, just ask for AUTOSTRADA per FIRENZE (a.k.a. "Autostrada del Sole" or Freeway of the Sun, called so since it connects the sunny south with the foggy north)

In La Spezia the rental offices are near the port (Avis is a bit closer to the station, but Avis is always more expensive).

Once you return the car, ask the rental office staff to call you a taxi. Take a taxi from the rental office to the train station (about 10 min). From there you can take any trains to the Cinque Terre villages (about 10-25 min depending on which village)

Thank you, Roberto da Firenze! I would way rather not go back go back to the airport. I was worried about getting out of Rome, but that looks easy enough. I appreciate the tips!! Now, if only May 28th would get here!!!

Two years ago we rented at the Hertz in Siena and eventually dropped it off in Orvieto. We stayed outside the walls at Hotel Italia, near the train station and the top of the escalator. We made day trips from Siena before moving on to other towns. The hardest part of driving is keeping your eyes on the road because of the scenery. We are going back in May.