Hi. I'm planning a 10 night trip to Italy in late May, as follows:
Venice - 3 nights
Tuscany - 2 nights
Rome - 5 nights

The question is: where to stay on the middle portion of the trip? My husband I have decided we really want to see the Tuscan countryside, specifically the Val d'Orcia, so Florence will only get a cursory visit this time around. We want to rent a car from Florence, dropping off in Orvieto, before proceeding to Rome. Given that, do you recommend:
A. Two nights Pienza
B. One night Florence/One night Pienza
C. Two nights Florence

It's just the two of us, late 30s. Since we will be arriving to central Florence via train, I do want to wander the city a bit, see the Duomo, and get a leisurely lunch. I can't imagine not seeing anything at all. We will arrive in Florence on a Monday, and I'm frankly okay with skipping the museums this trip; there will be lots of art throughout. Even so, I can imagine being frustrated if we need to rush to get the car that day, hence option B. If there's a good argument for C, we would plan to leave early in the morning and spend the day driving to Orvieto, rather than taking the high speed train.

I'm really torn on this. Thoughts?

I should add:
This is our first trip to Italy, though we are seasoned travelers. I'm aware of the driving restrictions in cities (not sure where we'll pick up the car yet). And, finally, I'm open to other options, like staying in another rural location the first night, if that makes more sense logistically.

I can see another option, which would be to take the train from Venice to Florence, spend until about 4pm or so sightseeing, pick up the car and drive to Pienza. If, after doing that, you really felt frustrated about how little time you gave to Florence, call the rental company and tell them you want to drop off the car in Florence airport instead of Orvieto. Do that, and spend more time in Florence before heading off to Rome on a late train. (You can put your luggage in the Florence train station).

However, you might feel after your day in Florence that what you really feel like doing is come back some day to Florence and spend 4 or 5 days there. Or maybe -- much to your surprise -- you both feel Florence didn't hold that much appeal for you (no explanations needed). If that's how you feel, then continue south to Orvieto and drop off your car in Orvieto, taking the train to Rome.

I also would say that if you really want to be in the countryside of the val d'Orcia, try staying on a farm rather in a town.

I also recommend that if you decide to visit Florence for lunch and sightseeing before going to Pienza, consider picking out 3 or 4 things to see, even if they are not museums, rather than just wandering around aimlessly. You don't need to go inside the big museums to some jaw dropping chapels or interiors. Don't pick more than you can easily handle and leave yourself time to stop and snoop at surprises in between each.

Lastly, I would enjoy a nice lunch but I wouldn't make it a big project. By all means don't gulp down food, but save the leisurely multi-course lunch for the Tuscan countryside and/or Orvieto.

I would choose Florence or Tuscany, not both. If you choose Florence, just train Venice-Florence and spend your two nights there. (That's only one full day for Florence, with or without museums.) If you choose Tuscany, pick up the car as you're leaving Venice and drive to Pienza. You'll have just one full day to explore a small part of Tuscany. If you want to see some of Orvieto, leave Pienza early, park the car at the bottom of Orvieto (to babysit your luggage), and return the car in the afternoon before you train to Rome.

If it was my choice, I'd skip both Florence and the Tuscan countryside and re-visit in the future when I had more time. But if forced to choose in your scenario, I'd go to Florence.

If you decide to drive, make sure you know all about the limited traffic zones (ZTLs) established in almost every Italian city and town. If you drive into the zones (even by mistake), you risk receiving traffic tickets in the mail after you get home.

If you choose not to go to Florence, you might prefer to take the train from Venice to Chiusi to pick up your car and have lunch there. It's a 4 hour ride, and If you are early risers, you can catch a train that will get you there before the rental offices close for lunch. But if you take a later train, Chiusi is a lovely Renaissance hilltown with a couple of excellent restaurants and quite interesting things to see, certainly enough to keep you interested until 3.30pm when the rental offices reopen. From Chiusi it is about a 30 minute drive to Pienza or a somewhere else in the val d'Orcia.

Horses for courses, but I would not wan to pick up a car in Venice and drive to Pienza. It's more than 4 hours of unattractive highway driving without factoring in stops for lunch, etc. I'd want to knock off some of that driving using the comfortable trains and scenic roads. So another possibility is to go Florence, but pick up the car at the airport there and then take a scenic route south to Pienza through the Chianti hills southeast of Florence, or the beautiful le Crete Senesi area just southwest of Siena. Either area would be a great destination for a leisurely lunch, and the roads from those areas to the val d'Orcia are scenic.

Have you considered taking a night from Rome and adding it to the Tuscany part? Two nights gives you one full day somewhere.

Did you plan to visit Orvieto or just drop the car? If you don't plan to visit Orvieto, you could drop your car at Chiusi and take the train to Rome from there (it's closer to Pienza).Are there any other towns you wanted to see besides Pienza?

Thank you all for the thoughtful responses. I appreciate the insights. I had considered taking a night from Rome, but as it stands we will only have 4 full days there for my Roman-history-loving husband. I'm now leaning toward Option A, and this is how I see it shaking it out. Monday is pretty full, but feels comfortable if we don't try to see all of Florence.

Mon - take train from Venice, arrive Florence around 10-11, get a brief taste/take notes for a future visit, pick up car mid-afternoon and drive to Pienza area (through Chianti?).

Tue - visit Montalcino and Montepulciano, enjoy scenic drive, find a great lunch, taste some wine

Wed - leisurely walk and/or drive for lunch somewhere near Pienza, drive to Orvieto and visit town, train into Rome around 6-7

A couple additional questions:
Do we need to pick up the car at the airport to avoid the ZTL? I think the highway drive Florence-Pienza is about 1 hour, no? With the sunset being so late, we might well have time to do a scenic drive even after seeing Florence - thoughts on time/routing? I'd love suggestions on Val d'Orcia places to visit/eat/drink.

If you take the train to Florence, put your luggage in the train station and go sightseeing, then return to the train station to retrieve your luggage, at that point it is almost six-o-one-half-dozen of the other whether you get into a taxi and go to the car rental offices that are near the Arno, or if you get into a taxi (or take the bus) for the airport and rent the car there. There are pros and cons to both, but a lot of people are swayed by the sheer terror of accidentally entering a ZTL and getting a huge fine. However, peope who rent a car near the Arno do report that the rental agents are very explicit about how to drive out of town without going through a ZTL, and can show you on a map. You can also ask a million times on social media (try the Slow Travel website).

It is actually closer to 2 hours to get to Pienza from Florence, even if you were take the highway most of the way. There are scenic routes south through the Chianti or through Poggibonsi down through Montalcino, but don't underestimate how slow going some of these roads can be especially in the Chianti hills. You won't be able to leave Florence until 4pm earliest unless you go to the airport to pick up the car.

Mon - take train from Venice, arrive Florence around 10-11, get a brief taste/take notes for a future visit, pick up car mid-afternoon and drive to Pienza area (through Chianti?).>>

do check that anything you are particularly interested in will actually be open on a Monday. [lots of museums close on Monday in Italy] probably it won't matter as you'll really only have time for a wander around rather than actually going into anywhere but I thought that it was worth saying.

really, I don't think that you're going to have long enough to make it worthwhile, and the effort is going to be out of proportion to the benefits.

You recognize that Mon will be a very full day, but Wed looks quite challenging to me as well. It doesn't seem like there is any time to actually visit Orvieto. The issue with your overall plan is that you're trying to visit 3 places-- Florence, Pienza (and surrounding area), and Orvieto-- in 2 days. I don't know that you'll get a satisfying taste of any one of them. In all three places, you will have that feeling hanging over you of only having X amount of time to squeeze in the next activity. You are using words like "leisurely" and "scenic" but I'm not sure you'll have much of that with the current plan.

Think carefully about what you want out of the trip. If your vision is truly for quiet walks, sipping wine. leisurely meals, and scenic drives, then spend both full days in the Pienza area. Or add a day there from Rome. But if your vision is more of rushing about, snapping a picture, then hopping back in the car/train off to the next place, then you'll be very comfortable. (Nothing wrong with that kind of trip, just want your expectations and reality to match).

The hardest part of planning a trip like this is deciding what NOT to see. All of the places you mention are lovely. You just need to decide which will match your personal goals for this trip. Happy planning and buon viaggio!

Be aware that many things in Italy are closed throughout the middle of the day. Not quite the problem in Florence as it is the other towns you are planning to visit, but timing is everything.

Once again, thanks for the feedback and the tips. Much appreciated. Sounds like I need a little more advice to try to trim this back. And perhaps I'm missing the implications of things being closed.

Really, we will not try to see all of Florence. We can eliminate Orvieto without difficulty. Drop car in Chiuisi then?

Cal d'Orcia does sound like my ideal Tuscan area, but would it make things easier if we chose Montereggioni or somewhere else closer to Florence (where?) Or one night Montereggioni, one night Pienza? I don't need to see all, or even most, of the towns, but we travel light and I don't mind changing hotels if the routing makes sense - e.g., moving north to south.

Honestly, in the time you've got, i would drop Florence [which as you recognise you can't see in a day or anything like it] in favour of Orvieto, which you CAN see in a few hours. The duomo is truly a wonderful work of art - just the outside is worth the trip. it would fit well into your schedule and would help to cut out those one night stands. I know that you say that you don't mind them, but they are very tiring and moving from one place to another, even by car, uses up time and energy better spent on seeing things.

honestly, if you want to see the Val d'Orcia, that's where you ought to go!

For me, visiting the Tuscan countryside is all about seeing the countryside. The landscape. My preferred visits to Tuscany are drive-throughs, with maybe one stop in one town to see some art work or historical site that I have heard about and want to see, and always a long lunch somewhere that eats up all the time when things are "closed." Sounds jaded to put it this way, but atmospheric hilltowns in Italy are a dime a dozen. They are all fun, and if you have time aplenty, it is great to just stop in any of them. But if you have limited time, save it for driving slowly and taking a chance on a few wrong turns just to follow your noses. Take a flyer on any town.

What closes in the middle of the day are shops. Some churches and small rural museums also close, so plan accordingly if there is something on your wish list, but otherwise don't worry about it. Go do some scenic driving after lunch.

I think it is a good idea to consider a shorter drive into Tuscany leaving Florence. Montereggioni or Montalcino, but I wouldn't switch locations.

True story: I headed out one morning from Montefalco in Umbria to meet friends for dinner near the coast in southern Tuscany. My plan was to visit Orvieto on the way and have lunch. But driving west, the sight of Todi glistening in the sun after a black-sky rainstorm was so beautiful, that I pulled off the road to take a picture. Unfortunately, the only turnoff available was the unpaved long driveway of a farm, and I was quickly trapped in a sea of mud. It took a couple of hours for two Italian farmers to get my rental car unstuck, and then another hour for me to get the car washed nearby. By the time I reached Orvieto, it was after 4pm, and I still had another 90 minutes of driving to get to my friends' house. I zoomed up the tufa town, found a parking lot, paid the meter for an hour's worth of parking, and literally ran up the steps to the piazza of the Duomo. Unbelievably fabulous facade. After some time staring at the outside, I bought a ticket to see the interior, and spend enough time inside to quickly see everything. Then I ran back to my car and made it to dinner at my friends' house in time.

I do NOT recommend (a) getting stuck in the mud, so do not drive off the paved roads if it has been raining or (b) racing through Orvieto. However, THE reason to go to Orvieto is to see that cathedral facade, and while I am sure the rest of the historic town is special, I would not make the best the enemy of the good, and thus I would drop off the car in Orvieto. I would leave the luggage in the trunk while I did my sightseeing and then drop off the car after, just before taking the train. I think if you will have more time than I did to stroll about, and while you won't see all of Orvieto by a long shot, seeing the cathedral is very worthwhile. If it turns out you only have time to drop off the car before catching the last train, well -- things happen on a trip.

I meant to add:

I personally wouldn't have a problem going to Florence for lunch. I'd probably get off the train, stow my luggage, and walk straight to the central market, buy food, then head out for some choice-gem highlights. Stop in a cafe for coffee, head back to the train station by 3pm. Pick up car by 4pm. Even if you picked up a car in Venice in the morning, you would not get to rural Tuscany much earlier, since you would still have to stop a couple of times and eat lunch. You are "losing" about 2 hours by having lunch in Florence -- but what a way to lose it!

One alternative I could see is to take the train to Florence and immediately go pick up the car and then head into rural Tuscany for lunch. Might be nice.

By the way, although I think the target areas of scenery in Tuscany are small enough to not need to switch locations, I don't find a few nights of one night stands tiring. It just doesn't bother me either.

You don't have to take the slower road (sr222) from Florence through Chianti on your way to Pienza (there are faster roads- sr2 or even autostrada). You don't have to drive through all the small towns in Chianti to reach Pienza.

>>>Cal d'Orcia does sound like my ideal Tuscan area,<<<

Then keep it in. This is the Tuscany you see on postcards. You will arrive Pienza later in the day (I have a list of places to stay in Pienza if you need suggestions) and the next day, you can head to Montalcino. I would pick other towns to visit closer to Montalcino (or the abby to hear the chants which is close), not Montepulciano (opposite direction from Pienza). On your departure day, you could stop in Montepulciano in the morning(it's between Pienza and Chiusi or the route to Orvieto).

You will need to work around the car rental hours (they will close for 2-3 hours in the afternoons). It would be possible to visit Montepulciano for a couple of hours in the morning, drive to Orvieto in time for late lunch. Turn your car in after the rental company reopens around 4 (they are usually open until 7 so you could stay in the old town of Orvieto until around 6 if you wanted). By keeping your rental car until later in the afternoon, it gives you somewhere to store your luggage (no luggage storage at the train station in Orvieto). Free parking behind the train station (or it was free last time I parked there). You catch the funicular up to the old town across the street from the train station. Trains to Rome are pretty much hourly until about 9 pm (takes a little over an hour to reach Rome). Last train to Rome is not until 11:30.

You really don't gain anything by taking the autostrade to Pienza. If you pick up the car near the Arno and take a route to Pienza via Monteriggioni and Montalcino, it is just a bit less than 2 hours and it is incredibly scenic. Taking the autostrade will be a bit over 90 minutes and not very scenic at all.

What really matters is how long you want to stay in Florence and when the sun sets. If you are on the road by 4.30pm, you could take the scenic route through Chianti to Pienza (via Greve/Panzano), which would take you about 3 hours without visiting the towns.

But if you would rather go down through Monteriggioni and Montalcino, if might feel like less pressure.

While I agree that if you want to the val d"Orcia you should go there (and Montalcino is in the val d'Orcia, as well as Pienza), but there are other highly photogenic areas of classic Tuscany that you've seen on postcards and you might want to drive though.

You might want to look on Amazon for a book with a title like "Best Drives in Tuscany" or "Ten Great Drives in Tuscany" just to get some general ideas. Many of the drives will be too far, and it is not a great idea to drive around Tuscany with your nose in book, lockstep behind other tourists. It's more fun to explore. But having some idea of the lay of the land ahead of time will help, I think

>And perhaps I'm missing the implications of things being closed.<

Not if you're planning on spending the hours at the middle of the day driving as sandralist suggests above.

I find that I don't really enjoy a small town as much when all the shops, churches and other things are closed up tight. I like the atmosphere in a town when people are out and about and I can do a little window shopping, tuck into a church,etc.

Even a late lunch doesn't take me all afternoon to eat, so if there's something in a town that I want to see, like the cheese shops in Pienza, I try not to be there between 12 and 4. For churches and small museums, I check the hours.

Oh, such helpful details! Val d'Orcia it is,keeping Orvieto, and incorporating your suggestions for routing. We have a reservation at B&B Camere La Vite, but it is changeable.

While there is a pay parking lot 2 minutes walk from your B&B, I usually find street parking (free) about a 5 minute walk away on Via Sarti Giorgio. The Coop grocery is near there too.