Private transfer Rome to Siena/Tuscany

What kind of driver are you? I don’t think it is a question about the roads of Italy, it is a question of if you feel comfortable driving in general, and in this case doing some minor research so you understand tolls, parking, etc. You don’t want to stay at an agriturismo without a car, as you’ll be trapped and at the mercy of paid drivers. What kinds of things do you all want to do? I make a list of the things I want to see and then choose the place that makes that most efficient.
What do the “kids” say—would you all rather be in a place you can walk to dinner, etc., or be in a rural environment? You have time for Florence and one other place in Tuscany, so as long as you can answer all those questions, you’ll arrive at the perfect solution.

Driving in Tuscany is no different than driving anywhere else. The roads are generally good and not crowded. You just have to do your homework about driving in Italy- ZTLs, parking, speed cameras, tolls. Follow the rules and all drivers must have an IDP- get at your local AAA before leaving US- it is required by law.

That said it would help to know where you are going after this time in Florence/Tuscany? Where will you fly home from?

It looks like you have 5 nights for this segment.
You could stay in Florence the whole time and take a few day trips- DIY by bus or train or with a guided bus tour or private driver

You could rent a car as you leave Rome and use it for a few nights (3) in Tuscany then drop as you get to Florence.

You could train to Florence from Rome spend 2 nights there (make a list of what you want to see and do in Florence- 2 fairly full days might be enough as long as one is not a Monday when museums are closed)
Then pick up a car as you leave Florence for 3 nights in Tuscany hill town.
A 3 night stay is really just 2.5 days. Location changes take at least a half a day.

We prefer to stay IN a town vs an agriturismo so we can walk to dinner and drinks. Don’t want to be driving at night and certainly not after having wine with dinner!

If you intend to wine taste then you must have a designated driver- the alcohol limits in Italy are much lower than in the states.

You could hire a private driver from Rome to Florence/Tuscany with stops if that fits your budget- figure several hundred euros. You can check daytrip.com for an idea of pricing.

We always book our cars thru AutoEurope.com- a US based consolidator with excellent customer service and usually best rates. Check their website for rates and what they offer. We always book with No Deductible/Full Insurance. It’s a few euros more a day for total peace of mind.

There are directions here on forum for driving both in and out of Florence or Roberto will generously update those as needed. Or you can pick up/drop off at the Florence airport. Your choice.

There are recommendations here for hotels in or walking distance into hilltowns with parking. Just ask.
For the most part you will not be driving IN to any hiltown- parking is in lots outside the walls.

It appears that you have changed itinerary since this previous post?
https://community.ricksteves.com/travel-forum/italy/home-base-thoughts-for-tuscany
Could you update here and let us know what full itinerary is now?

Hello, yes, I have changed our itinerary for like the 100th time… Plan is now as follows:
May 25 - May 28: Rome
May 28 - Jun 2: Depart Rome in AM and head towards Florence, Tuscan towns
Jun 2 - Jun 8: Depart Florence in PM on high speed train to Amalfi Coast
Jun 8: Depart Naples for home

So since you reminded me of Monday being no good for museums, looks like we need to head straight for Florence and then do Tuscany May 31-Jun 2 Could do a little Tuscany guided tour by car and then be dropped off in Florence at train station in time for train to Naples/Salerno. Or could rent a car and do it ourselves. I’m just having a hard time choosing which towns. I think we would be happy with most any of them, but probably would rather stay in a town now I thinking. We do not drink alcohol, but do like good food, olive oil, etc. And would rather be busy, active rather than relaxing, slow pace. Sleep at night is enough relaxation for us. I can relax at home, 🤣🥰 I hope this helps you to answer my questions a little better!!! Thank you
So much for your time!!

Which Tuscan towns are you interested in?

Where will you stay on Amalfi Coast?
Make sure you have figured out time and transportation to Naples for your departure flight.

Siena is easily done by bus from Florence- although it is worth an overnight.
Lucca/Pisa easily done by train- can be done on same day. Both are too far west to use as a Tuscan base.
San Gimignano and Volterra are a pain by train/bus so a car would be useful or a guided bus tour. Both are overrun with tourists.
The towns we love are in the Val d’Orcia region- Montepulciano, Pienza, San Quirico, Bagno Vignoni, Monticchiello, etc. This is where the scenery you are probably thinking of is. Really need a car for that area. There are a few agriturismos here that are very close to the towns.

My choice would be train to Florence from Rome 2 nights- plan well if a lot of museums are on your priority list. If you can add a night I would add to Florence and do a day trip to Siena (maybe take 1 night from AC)

Pick up car as you leave Florence- head to Pienza or Montepulciano for a 3 night stay. That gives you 2 full days to drive around and see the area. You can drive the Chianti road (SR 222) from Florence past Siena. (Be careful stopping and parking with luggage in the car- make sure it is well hidden and take valuables with you)

Drop the car in Chiusi- (Avis or Budget I think?) catch train to Salerno- change in Rome. Chiusi is a quick and scenic 45 min drive from Pienza.
Or keep the car and drive all the way to Salerno. All freeway- not difficult- about 6 hours.

This is a big help!! Yes, Val d’Orcia sounds beautiful with the hilltop towns and/or walled towns. Siena day trip sounds great! I’ll ask my husband how he feels about driving. I get too stressed out and want to look at everything and then my driving isn’t so great. 🤣🥰

Christine's plan in her last comment is the best plan.

If you want to minimize driving, especially in a city, you can take a train from Florence to Chiusi, and rent the car in Chiusi (pick up and return there) and do everything else by train.

Be aware that the Chiusi location has only one AVIS-BUDGET agency (walking distance from the station), so if you select that location AVIS-BUDGET is the only option (you can select it with www.autoeurope.com, if the deal is better than directly with Avis). It's a franchise office and it is not open on weekends (it's closed Sat. afternoon and all day Sunday). They also observe a long lunch break. So time your pick up and return accordingly if you decide on renting a car in Chiusi.

Avoid using the car for Lucca and Pisa. Pistoia and Arezzo are also two popular destinations by train from Florence. Siena can easily be done by train or bus (bus more convenient). You definitely need a car for the Val D'Orcia (Montepulclano, Pienza, etc.) and certainly you need a car anywhere if you choose to stay at a farm (agriturismo)

Another option if your husband really does not want to drive at all

Train to Florence from Rome
Florence 3 nights-1 day could be day trip to Lucca/Pisa (although I don’t think either are necessary)
Bus to Siena-drops you up in town
Spend 2 nights-Siena is magical at night

From Siena do a guided road trip to Val d’Orcia area
ToursbyRoberto. Com gets excellent reviews-I think he usually includes winery visit but I am sure you can personalize instead
He is based in Siena and books up early so don’t delay if this interests you

It’s then quicker to return to Florence from Siena and catch fast train south
(I would probably grab a taxi down to train station rather than bus for this return trip)

Hi Christine,

I have looked on Tours by Roberto website and didn’t see a tour with the Val d’Orcia name, but is the “Heart of Tuscany, Siena’s Southernmost Corner” the same thing? Could do that on Monday and maybe I could find a day tour that goes to Volterra for Tuesday and get dropped off in Florence at the train station late that afternoon so we can head to the Amalfi Coast.

If we rent the car, my thoughts are as follows:
Get car in Florence and leave Sunday morning for Siena. See Siena all day Sunday and spend the night. On Monday head to Volterra stopping at Monteriggiono on the way (on the road between Colle Val d’Elsa and San Gimignano, stop to see at the “towers”). Then drive back to Siena on the more southern route and stop in Casole d’Elsa (I read that it’s worth a quick stop?). Then we can do the Val d’Orcia on Tuesday, starting at Montepulciano and ending after the La Foce Gardens and heading to Chiusi to return the car and get train to Amalfi Coast. Does this sound doable to you?

If both of these are doable, I’ll ask my husband which one he would prefer and then we can decide! Thank you so very much!!! Loads of help!!!

Yes the “Heart of Tuscany, Siena’s Southernmost Corner” is the tour you want. He stops in Montepulciano and Pienza and I believe Bagno Vignoni or San Quirico as time allows. Also stops at an olive grove for olive oil making demo.
I think the tours are customized- first come first served- so if you are first to sign up that day for the Group- tour to Join- you get to set the itinerary.

JMO- but I think you are simply trying to squeeze too much in. Driving in Tuscany is easy but slow going.

get dropped off in Florence at the train station late that afternoon
so we can head to the Amalfi Coast.

Getting dropped at Florence station to catch a train- where will your luggage be this day? Train to Salerno is a 4.5-5 hour trip- that’s getting a bit late to arrive on AC- again- where are you staying while there?

Get car in Florence and leave Sunday morning for Siena. See Siena all
day Sunday and spend the night. On Monday head to Volterra stopping at
Monteriggiono on the way (on the road between Colle Val d’Elsa and San
Gimignano, stop to see at the “towers”). Then drive back to Siena on the more southern route and stop in Casole d’Elsa (I read that it’s worth a quick stop?).

Have never stopped not sure it’s a necessary stop.

Then we can do the Val d’Orcia on Tuesday, starting at Montepulciano and ending after the La Foce Gardens and heading to Chiusi to return the car and get train to Amalfi Coast. Does this sound doable to you?

Check La Foce gardens- they are only open a day or 2 each week.
ETA--only on Wednesday
https://www.lafoce.com/en/timetables-tickets

This is a heck of a lot of driving in one day. Not much time to actually enjoy the towns or gardens. The car rental agency will be closed til about 4-4:30. Check train times after that- puts you on AC probably 10 pm.

See my warning above about parking with luggage in the car. It’s a risk- not insurmountable if you prepare but keep in mind.

I get wanting to see it all but you just can’t with the time you have. Those medieval hill towns are not going anywhere!

Hi Christine,

Well do you think just doing a private transfer to Sienna and then the Val d’Orcia tour with Roberto on Monday would be better then?

If you think you are OK driving around a little bit keep it at an hour or so out and back each day. That will probably end up being 1.5-2+ in and out from base. Each town deserves more than an hour.
I know I suggested driving all the way to the AC! I don’t think you are ready for that.
It just seems to me that you are not at all sure your husband wants to drive anywhere. That’s OK.
It’s really not that much fun for driver- have to keep eyes on the road.

Well do you think just doing a private transfer to Sienna and then the
Val d’Orcia tour with Roberto on Monday would be better then?

This is a very good plan. Driver can include stop in Monteriggioni or a Chianti village, drop you right at your lodgings in Siena.
Make sure you give yourselves enough time in Siena.
If I didn’t want to drive in Tuscany I would absolutely look at a toursbyroberto or similar tour.
You can’t go wrong staying in Siena.