I'm planning to spend a week in Tuscany (solo) as part of a trip to Northern Italy next May. I have been to Florence (briefly) before, a long time ago, seeing the Duomo and Acadamia, but not much else. I want to see some hill towns, and Siena, and probably spend some time seeing things in Florence other than the two aforementioned sites.

Right now, I'm thinking about picking up a rental car at the Florence airport (arriving by train from somewhere else, so no jet lag issue), then heading to San Gimignano, and possibly Monteriggioni on my way to Siena, where I would stay for two nights (will have to find parking, but I think I have that sorted), then head to Montepulciano or somewhere nearby for 3 nights, before returning to Florence to drop the rental car and spend two more nights.

I've also considered staying at one place (like an agriturismo) for a week or five days, and perhaps driving longer distances to do daytrips as an alternative to having 3 separate bases, but I have reservations about doing that much driving.

So, I'm interested from some input from people who have done this, either spending a week in one place or moving around as suggested. I guess I would say that, for me, Siena and hill towns are a priority, but it would seem a bit strange to do Tuscany without spending some time in Florence.

Over multiple trips, we've stayed in lots of towns because Tuscany is big and varied. Unless you're ok with spending hours driving, you'll only be able to see a small part of the region in 4-5 days, so you'll have to be very selective in your sightseeing.

One thing you might consider is continuing to Siena by bus from the Florence train station rather than going to the airport to rent the car. (Or, depending on where you're coming from, train to Siena rather than Florence.) After your time in Siena, rent a car, explore wherever, and then return the car there before heading to Florence.

IMO Siena is both good and not so good as a base for exploring. It's central for reaching very popular parts of Tuscany, but by my definition it's not a "town" but a good-sized city with somewhat typical city traffic patterns on its periphery... heavy in the morning as you're leaving and heavy in the afternoon as you're returning. The Hotel Palazzo Ravizza had easy ingress/egress and worked well for us, and walking from there to main sights in the town is easy.

I hope you can arrange to spend that one full day in Florence on a day other than Sunday or Monday. Lots of things you may want to see could be closed on one of those days. To make the most of your time, get entry reservations wherever possible.

Good to know about Palazzo Ravizza, because that's where I'm hoping to stay in Sena.

My hang up on renting the car in Siena is that I'm going to want an automatic. While Auto Europe says that's possible in Siena, it looks like a place where there might be limited choices. While I can drive a standard shift on flat terrain, the thought of negotiating hills with a stick is frightening (I've never owned a stick shift car, just driven them a few times).

On Florence, I would probably be arriving on a Monday and departing on Wednesday, so Tuesday would be my day for seeing the sights.

I do plan to go back to Tuscany (and Umbria) at some point on another trip. I'm really intrigued by Orvieto, and would probably work my way north from there. But for this trip, I don't think I'll get south of the Val d'Orcia. This trip, I'm flying in and out of Milan (at least, that's the plan as of now). Next trip, I'll fly in and out of Rome, most likely.

Have you decided what you want to see in Florence? Maybe it will be enough for you, but one day is not much, even if you've seen a few things there before. For comparison, I with I'd had more than four full days ... and those were packed from morning to night!

You might not be driving many hills of any steepness because you can't drive INTO most towns. You have to park outside and walk in/out or risk receiving a traffic citation (or two or three) after you get home. If you're not familiar with the ZTL program, learn the signs and keep your eyeballs peeled.

https://mominitaly.com/ztl-in-italy/

I assume the comment about Orvieto relates to a future trip. If you make it to Orvieto in the future, look into visiting Pitigliano and the "sunken roads" in the Sovana/Sorano area. About an hour west of Orvieto and all very interesting.

https://www.maremmaguide.com/via-cava-di-san-rocco.html

kja: I am sure I could spend a week in Florence and find plenty to see, but, for this part of the trip, I am prioritizing smaller towns and landscapes, to a certain degree. I will be including Milan and Bologna, neither of which I have visited before, so I will have a mix of urban and rural.

Jean: Yes, Orvieto is for a future trip, and those do look like good targets for the next one. I am aware of the ZTL, and will try to have those scoped out in some detail before the trip. It’s one of the factors I’ve looked at when considering where to stay if I end up staying in Siena and Montepulciano proper. I take it that you can get to the parking lot for Palazzo Ravizza without having to encounter the ZTL?

Sounds nice! Enjoy.

You can learn about the ZTL in Siena here:

https://www.accessibilitacentristori...any/siena.html

I typically search ZTL maps/hours, etc., when I know which towns I am visiting. Click through to see the Google version and select parking. Zoom in. Find a parking lot outside the restricted area and hoof it in. If I have a lot of time, I do some cross-referencing because, well, you know, things change. (Fingers crossed this method continues to work for me--and you too.)

Unless things have changed in the last couple of years, the parking lot at Palazzo Ravizza is outside the ZTL (while the road on the hotel's entrance side is inside the ZTL) and driving to/from the lot is just a few turns off SS674 which runs north and south on the west side of Siena. You are allowed to drive to the entrance and drop off or pick up luggage. The hotel will report your car license plate to the polizia so that a citation isn't issued.

Here's a ZTL map for Montepulciano which also shows parking outside the zone. If you pick a hotel in the lower areas to the north and south of the historical center, you can avoid driving steep roads but still be within an easy walk of the center. FYI, even a confirmed car rental reservation that indicates auto transmission is not a guarantee there will be one for you, even at Peretola Airport.

https://www.accessibilitacentristori...pulciano/mappa

I hope you're not planning to drive into Bologna.... The ZTL is huge and the boundaries are a bit truncated.

We just got back from a similar trip: Bologna, Cinque Terre, San Gimi (2n), Montepulciano (4n), Florence (1n), Ortisei, Munich. I can share my thoughts on the Tuscany part. We picked up stick shift car at Pisa airport and drive to check in SG, returned car to Florence airport, taxi to Florence hotel. We enjoyed SG a lot and drove by nearby town/winery for scenery. Could have time to make it to Volterra, but DH is sick so that didn't work out. The scenery in the area is breathtaking, but there's not much area to stop or picnic on those routes. From MP, we visited nearby towns like Pienza, Monticello, San Quirico and the Rick Steve drive. Literally drive the loop of sp146 would give you the best scenery. In MP we parked outside the ztl but 5 min walk to lodging. Your host could give you ideas. We did one day trip to Siena and worked at Il Campo, not ztl and 10 min walk to town, very clean underground garage. I would have taken one night out fro MP if I knew the garage is quite safe for our luggage. We have been to Florence and arrived Friday PM. That evening we wandered areas and had Florentine steak. Next morning we booked 8:15 am Uffizi and it worked out great. Then train to Bolzano then bus to Ortisei.

I am not sure if the parking lot of the Palazzo Ravizza is in or out of the ZTL but it is located right in back of the hotel and you do have to go through the ZTL to drive to the hotel. The hotel is a pleasant 3 star quality hotel. GPS does not do a good job guiding you to the hotel but once you have driven in it becomes easy to get in and out. We did not experience bad traffic getting in and out of Siena. It is nice to come back to Siena for the evening and have an easy walk to a restaurant. Siena is a good location from which to explore Chianti, Lucca, San G etc. Agree that it is safer to get a car in Florence at the airport then Siena if you need an automatic

There is a "how to get to our hotel" map on the Palazzo Ravizza website, and they mention that GPS will not provide the right directions.

https://palazzoravizza.it/en/where-we-are/

Jean:

I definitely won't be driving in Bologna. I will drop the car at the airport in Florence, and use trains for the remainder of the trip. I will have the car either 3 to 5 days, depending on whether I decide to pick it up in Siena or elsewhere (probably Florence airport). I'm undecided on lodging for Montepulciano or that area. I've got my eye on a hotel and a couple of rental apartments in Montepulciano (might be a good opportunity to do laundry midway through my trip), but I'm also interested in some of the agriturismos I've seen in the area. Staying out in the country would certainly answer overnight parking questions, but then again, you don't get to enjoy Montepulciano in the morning and evenings before the day-trippers arrive, as I would be one of them.

We loved our stay at Hotel Palazzo Ravizza in Siena, and we had a rental car, too. No problems at all. The views from our hotel room were spectacular! It was easy to find the hotel and their parking lot as long as you follow their directions. They provide you with a map.

We also stopped in Monteriggioni on the way from Siena to Florence, and we absolutely loved visiting here. It was peaceful and serene before the frenzy of Florence.

Also want to add that for bases, we spent 3 nights in Lucca, 3 nights in Siena, and then 4 nights in Florence. I realize that Lucca won’t work for you because of what you want to see. I wish we had 4 or 5 nights in Siena. There is never enough time for Tuscany.

I’ve toyed with Lucca, but I’d have to eliminate or cut back Cinque Terre, most likely. Always difficult to walk that tightrope between seeing as much as possible and going so fast you don’t do anything justice.

FWIW, not everyone here is crazy for Lucca. But it would be easy to reach between the CT and Florence and vice versa.

Tuscany is huge... almost 9000 square miles. There are lots of great things you won't be seeing in the time you have, so prioritize prioritize prioritize.

As another huge fan of Palazzo Rivizza in Siena, yes you must drive into the ZTL to reach their parking. That is no problem, each time you park you then report at the main desk that you drove into the ZTL, and then also when you're driving out. On our day of arrival, we parked at a city lot just outside the ZTL, which is close to Palazzo Rivizza, to make sure that they had parking available in their lot. We probably didn't need to do that.

In terms of driving a stick, there are many rolling hills in Tuscany, but not so many stops where you would have to start a standard transmission. Especially in Chianti, if you drive there, I was shifting up and down a lot, but at normal speeds that's usually pretty easy (caveat, I've had a stick shift car most of my life, so I don't even think about it).

San Gimignano is a total zoo during the day, but tends to be much quieter at night, I think you'll enjoy it. If you like to walk, there's a walk outside of the walls that's particularly nice in the early morning.