Sorrento to Siena by car - stop in Orvieto & "Heart of Tuscany" Drive

Having been to all the cities you named, but not by the same route, I'm inclined to say that the self-drive in that amount of time is a delusion of American mobility. There's plenty of traffic and forgettable divided highways, and annoying no-car zones and (in high season) crowded parking lots. There is plenty of rush-hour traffic just from Sorrento to Naples, let alone getting past Rome. Orvieto may be the exception, since they have a highrise, U.S. mall type parking garage, exactly what you need for this plan. But if you spend enough time in Orvieto, you'll hit dusk in Montepulciano. Do you know where you're going to park in Siena? Have you mapped it out on Google Maps and added 15%-20% to the time? What is the month and day of the week of the trip? I don't happen to know the duration of Rick's car tour route.

I'd suggest train to Orvieto and rent there. But you have to see what times of day that works out to on Trenitalia.

Thanks Tim! I got a laugh out of your "American mobility" comment. :)

We are staying in Siena and our hotel has free parking there.

The "Heart of Tuscany" tour takes about 2 hours round-trip from Montepulciano.

We will be traveling at the end of August on a Thursday. A google search says it is a 4 hour drive to Orvieto, and then an other hour to Siena, but of course, I have no idea what to factor in for traffic.

Thank you for your help! I want to be realistic.

The other factor is Orvieto itself. It's not a one-hour sort of destination (it's not a tiny place), and you need time for your meal as well. A worthwhile lunch will take at least 90 minutes.

I considered taking the train, but there is a group of four of us. From my understanding, we would have to take the train from Sorrento to Rome, Rome to Florence, then Florence to Siena. So three train changes. The train estimates a 7 hour trip. Google estimates 5 hours driving, and we would have freedom to explore along the way. I was thinking if we left by 8am, we could check into our hotel by 7pm, leaving us 11 hours to travel and make a few stops.

Is this naive?

Our trip doesn't really help in analyzing yours: We rented our car in Civitavecchia early in the morning, and visited Viterbo for about two hours, then getting to Orvieto just in time for a late lunch. By selecting a restaurant in many guidebooks but reading descriptions carefully, we managed to avoid a 2-hour lunch but had freshly-prepared food and noticeable air-conditioning. We loved Orvieto, and were sorry to leave around ? 4PM. We checked into our Sinalunga resort hotel in plenty of time to have a small-dish dinner at the bar, not having to wait for real restaurants to open.

It's much easier to drive around Tuscany, and much prettier, than around Naples and Rome. I found the (daytrip) approach to Siena very difficult and slow, with ZTL signs and no help from my Garmin, which kept telling me to go through the ZTLs, although I had the coordinates of the huge, outside the walls parking lot I wanted to use.

What I would suggest is that you think about your navigation experiences at home. GPS and Google Maps seldom take into account the width of a road, or the number of mall traffic lights or school busses on the road. Traffic is unpredictable, as is construction in a country where you don't live. I found that every lovely Tuscan hill-town was well off the main road, with twisty two-lane roads (through lovely countryside) making the approach to multiple, small, FULL parking lots always longer than I expected. (I'm not slamming Tuscany, I'm just responding to your question about obstacles to your plan!) We had wonderful days when we did not have a "Rick Steves" (sorry, Rick) schedule to check five boxes each day. We had a list of towns that might be nice, and when a day went well, we went to up to 3. Sometimes we got good recommendations from waiters at the lunch restaurants. Some towns were more of a "ghost" of a medieval village, but with good views. The church was locked, so we moved on. With more research, I might have known which of the two restaurants was the better one. [Edit: I was waiting to remember, that is a story about Sant' Angelo in Colle, visible from the Poggio Antico winery ... a sweet little memory of a medieval village, that takes imagination to enjoy. We were already in the neighborhood, so it wasn't a disappointing "detour". https://goo.gl/images/nGvF52 ]

I might note that we made a decision to eat heavily at lunch (often at a pre-booked winery restaurant) and only at our hotel bar at night, because we also like to go to bed early. I'm not pushing this for other people ...

I read this post and logged off my PC thinking that I shouldn't touch this...but here I am....I must respond.
Your plan looks like it will be a virtual nightmare... 4 people jammed in a car trying to connect all of those dots in one day! No way!
You will literally need to spend most of the day on the autostrada with the hammer down just to make each stop, never mind trying to actually stop somewhere along the way to take in the sites. It's 4 hours minimum to Orvieto. If you leave Sorrento by 8:00 you'll roll in to Orvieto just in time for lunch. If you park at the parking lot near the funicular/train station, if you eat at the small place at the bottom on the left and have a quick carbonara and water, you'll burn over an hour. If you take the funicular to the top, rush around like crazy and return to the car you'll burn at least another hour and see next to nothing. Then back into the car, hammer down to Montepulciano, one more hour, find a place to park....it's 4:00 if you are lucky, race around there for an hour plus and then off to Siena...
You'll arrive in Sienna by 6:30/7:00 and feel like you just just rode a mule into the grand canyon and walked all the way back out.
You need to make your choices and decide how much you want to see, if you care to ride around in the Tuscany countryside, whether an hour breeze through in a place you can easily spend half a day in is going to satisfy you.. Speaking from my experience and preference, that does not sound like a very satisfying trip. Orvieto is a very interesting place. You can easily spend 3 or 4 (or more) hours here. Just a few minutes away (you have a car!) is Civita di Bagnoregio, such a cool place to visit....and yet, a few more hours to enjoy. Montepulciano has been RS'd to death and although it's an interesting place...there are far more interesting places that you won't see. Tarquinia, a World Heritage site, an hour and a half from Orvieto (in the wrong direction) is far more interesting and less trafficked..
The point being, you are trying to do too much in too little time. Can it be done, yes, more than likely...but speaking from my experience you might enjoy your trip more if you try to do less. I would probably take the train to Orvieto (not the first to suggest it) and pick the car up there...then I would stay in that area and skip Montepulciano on my way to Siena. Assuming that your Siena visit is not also so frantic and assuming that you really want to visit Montepulciano, I'd drive there from Siena.
Good luck and please accept these comments as an attempt to provide helpful advise, not to be critical...until you try it you won't fully understand...oh, and try the squab in Orvieto (if you have time).

You don't say if you've driven in Italy before, and if you haven't, please read this and download their PDF.
There's a lot of info regarding ZTLs especially since you're hotel is in Siena. Included in the PDF tons of info on driving on both the autostrada and the roads connecting the hill towns.

https://www.italybeyondtheobvious.com/dont-mess-with-ztl-zones

I've been driving the route you plan on for many years, this defiantly has helped in the past.

How many nights do you have in Tuscany?

Thanks for logging back in and commenting Mack! This is exactly the feedback I was looking for. It is so hard to plan a trip without being there.

Basically, we need to get from Sorrento early in the morning to Siena that night. Our hotel has parking, and we have the next day to discover Siena, so we only have to arrive in time to check in. Anything we visit in-between Sorrento and Siena is a bonus. Sounds like maybe we would be better off skipping Orvieto or skipping Montepulciano. We are going to a family reunion for 5 days of our trip near Rapallo and a few days near Alba. Perhaps that will give us enough of a taste of the hill-town atmosphere? Which would you recommend skipping?

Also - two people have suggested taking the train to Orvieto and then renting the car to Siena. Do you think even with four people (two are 70 years old), that switching from train to car there is the better option over driving? It just seemed like it would be less of a headache to switch, but you guys are the experts so I definitely would take your advice if you really feel train to Orvieto then car is the best option.

Thank you to everyone for your help! This day in our itinerary is giving me the most hesitation. All of our other days we are staying in the same city for 2-3 nights.

Thanks Again,
Karen

Karen,
It is totally unreasonable. We drove from Rome FCO airport to our agriturismo which is 30 minutes north of Siena. We spent 1/2 the time on the Autostrada and the rest of the time driving through the Tuscan hillsides. It took 4 1/2 hours in mid-December with light traffic. Personally, I could spend an entire day exploring Montepulciano and driving from there to Siena.

I checked the train time from Sorrento to Orvieto and it is 5 1/2 - 6 hours! Is there any way you could leave a day early with Orvieto as your destination, then take a day to drive from Orvieto to Siena via Montepulciano? Could you at least leave half a day early?

As others have mentioned, what's the point of the brutal day you've planned? You'd have absolutely no time to see what you've set out to enjoy. I shudder to think of the itinerary for the rest of your trip.

It occurred to me that we haven't discussed Sorrento-Naples, which trips up many posters on this board. Whether you pay 99 Euros for a car and driver, or cram those poor feeble 70-year olds (I'm 66) onto the Circumvesuviana with no luggage racks and begging musicians, you still have to change in Naples, to a Frecciarossa ticket that may be non-changeable if you are delayed. I believe you need to rent a large, air-conditioned car that will be hard to drive around corners in medieval towns, and drive.

Since Google Maps shows 5-6 hours from Sorrento to Siena, I would predict that a straight through drive would probably take an even 8 hours. If you have a good trip, the massive garage in Orvieto is perfect for any size car, so stop for a few hours. If you encounter a lot of delays, maybe not. When we drove through Tuscany, the divided highway had plenty of one-lane and narrowed-lane construction zones, just like U.S. interstates (but without the truck climbing lanes.)

It sounds like you may have been to Italy before. So maybe you don't need Florence But another option would be to take the train to Florence from Naples, which can be under 3 hours with no changes. (Yes, you have to get to Naples to say "no changes" after Naples.) THAT is catering to elderly relatives. Sitting in a car for 8 hours is not! (Smiley)

Ok, so based on all of your feedback, I am thinking of changing to this:

Originally, we were driving from Sorrento to Siena, staying the night in Siena, touring Siena the next morning and then going to Florence for the next few days.

I am thinking maybe we are better off taking the train to Florence and checking into a hotel there on the first day, see a few things in Florence. Then day-trip to Siena the next day. That keep us from changing hotels again and driving in Italy altogether.

Right now we have 2 1/2 days touring Florence, plus what we set aside for Siena. Would you recommend seeing more of Florence instead and skipping Siena, or seeing Siena and Tuscany area with the extra day?

Perfect feedback Tim! I was getting hung up on how to even get from Sorrento to Orvieto. Trenitalia doesn't show any tickets to/from there. I also don't want to make travel more difficult for my parents, but maybe the car is actually the most difficult option.

So we could essentially take an early-morning Circumvesuviana train to Naploi Centrali, then switch trains to Trenitalia traveling to Florence. then day-trip to Siena by bus the next day? Is that a better plan with 70 year olds?

It is hard to find information about the frequency of Circumvesuviana trains. Are there only a few a day?

Well, Florence is not a substitute for the hill towns of Tuscany, but I was actually proposing a nice walkable visit with an overnight in one of the overwhelming Art History monuments of Europe. We (long ago) happened to stay in a hotel within view of the Florence train station, which I would usually avoid. But it was a quiet rear room, with immediate local bus access, and we were coming in and out by train. I was proposing that you rent the car for the rest of the trip in Florence. I wasn't urging you to visit Siena as a daytrip, because you said you wanted to stay there. I imagine that Siena and Florence will be equally crowded in August, but I think Florence will be a little bit cooler. Note that they are not comparable artistically and culturally, because of the late arrival of the Renaissance in Siena. But neither can be exhausted by one overnight stay. Speaking of exhaustion, how do your parents feel about air conditioning?

People have posted here often about bus or train daytrips from Florence, but that is usually because Florence is a focus of their overall trip. I don't think that is your own intention. There is no doubt that any visit to the Tuscan hill towns benefits from having a rental car. I wasn't denying that!

I think that if you have three nights ?? in your original Siena hotel, AND if the parking is easy in and out, there is no reason not to stick with your general plan. The fact that Florence is BEYOND Siena does not cancel the convenience of training there. I just thought it would be too bad to be in Florence (if it were the first time) and not see some highlights. But you could just rent the car and immediately drive on to Siena. Note that I implied earlier that Siena is not a tiny rural hill town. It has annoying traffic and industry on the approach, and you should ask your hotel in advance how they deal with the ZTL restrictions. If I had the choice of ONE night in Florence or ONE night in Siena, and had been to neither, I would choose Florence. The fact is, you can't "see Tuscany" or "see Florence" in 24 hours. We spent three or four nights in Tuscany, and never got bored. But we did get hot! And it was an entirely separate trip from our 1989 first-trip to Italy, which had four nights in Rome, three nights in Florence, three nights in Reggio Emilia (special personal choice, not a must see for all) and three or four in Venice, from where we flew home.

The Circumvesuviana timetables are here:
http://www.sitabus.it/en/circumvesuviana-timetables-and-rates/
http://www.sitabus.it/circumvesuviana_sorrento-napoli_al19082015/

Note that the Administrator's 2018 post refers to a file dated 2015. Welcome to Southern Italy.

Others here focus on the premium-priced subset, of Campagnia Express trains on the same tracks, very infrequent, because they are not jammed and gritty like the regulary, half-hourly +- daytime Circumvesuviana service. But we just took the Circumvesuviana into Sorrento, and (as a result) a car service back to Naples. Before taking the Circumvesuviana, you should use the Search box top center to read comments about it. You'd have to take a taxi to the Sorrento rail station, which has an elevator to the tracks.

Your plan is very ambitious. The distances are not short.
I wouldn’t worry about the traffic, because you won’t be driving through the city streets of Naples, and any morning commute snarls from Sorrento won’t delay you more than 10-15 min.
The problem is that by the time you depart Sorrento to the time you drive to and have parked in Orvieto (360km away), about 5 hours have gone. You mentioned lunch. Sit down at any restaurant in Italy and two hours are gone, at a minimum. Fast and lunch (or dinner) in Italy don’t appear in the same sentence. If you stopped in Orvieto I presume you want to spend some time in it. That is up to you but a couple of hours at least, assuming you just look at the Duomo. From the time you go down to your car, drive out to Montepulciano, find parking in Montepulciano, walk inside the walls, and 1.5 to 2 hours are gone. Montepulciano can be visited in a couple of hours. The drive to Siena is over one hour.
As you can see, the transfers alone will take most of the day. Your plan is doable only if you do a drive by visit and skip all meals.