I am lost!! Planning an early September Honeymoon that includes 4-5 days in the Tuscany area and I can't figure out where to stay. First I will have a car the entire time. Second we will go to Florence for 1 day (have been before, but going back just because, well, it's Florence!) We will also make a stop at Pisa 'cause I have to be a tourist for a minute. Neither one of us has been to Tuscany before and it is our honeymoon so we want romance and restful and not packed with other travelers. So here is my debate - I first thought I wanted to wake up and be able to stroll out of my hotel and wander in town to get breakfast and see the shops opening in this quaint Italian town. But what I am finding is larger towns with swarms of tourists and nothing quaint and charming. And I realize I want to open my window and see olive trees and rolling hills and be in this rustic villa and not a "modern" or "semi modern" hotel. But then I lose the close to a town thing. Other than my Florence day I thought we would drive around and go to vineyards, stop in a town for lunch, cheese shops, Olive oil etc. Am I stuck in a movie and this is not reality? Do I need to plan every day out or can I just see where the road takes us? Will I stumble upon things just by driving around or should I research specific routes? Google search shows me lots of romantic Tuscany that is south of Sienna - should i be that far south or should i be someplace in between Sienna and Florence? Thanks for your help - I know this is asked a gazillion times,but I'm stuck!

First, understand that a car and Florence, Pisa, or Siena is a toxic mix unless you have thoroughly studied the ZTL impact before approaching any Italian cities. Practically all communities have this ZTL restricted car zone. It is that some cities are especially zealous in their quest to collect fines from those who think they are invincible. They use video cameras to make sure no one escapes paying breathtaking fines if they wonder into these zones.
First, you cannot just drop into a vineyard and expect to be accommodated. Unless you speak Italian, you need to make a appointment at the time English speaking person is available to accommodate you.
Same for lunch. If any place is ok, it does not matter. If you want to go to a well known restaurant and want a table overlooking the “rolling hills,” you need to make a reservation.
Many people come here with either or proposition: plan every day out or where the road takes us. You don’t have to settle for either of these extreme positions. Understand that the opening days/time might not match you vision. Planning day out would make you understand the practicality of connecting venues on open days and hours.

San Quirico d'Orcia is a nice town. I'm not sure why it popped into my mind, but it sounds like a good fit for you. In a completely different direction, Vinci has it's charms and is not overrun by tourists. Wineries are not like those in the US and one can't just stop in. However, many towns (nearly every town) have great tasting rooms, enoteca, food shops, etc. And you can arrange a winery tour with several companies that will set you up and even include lunch or olive oil tastings.

www.chianticortine.it Check this one out. It is an easy drive to both Florence and Siena as well as a number of the hill towns. When you scan the landscape you will feel like you are in the movie. We have stayed there before and are going back in a few weeks.

Thank you all for the insight. Greg you are scaring me a bit - are you saying that I should not have a car to tour this region? Or just that I should take mass transit to the main cities? Seems like i should definitely do some planning to make sure I get at least a few reservations places. It sounds like random driving is great for scenery, but I should research a few towns that interest me and plan to drive to them each day correct? Is it feasible to go to say 2 small towns in one day?

Letsgeaux that hotel looks wonderful - unfortunately all the villas are booked on my dates, but that is totally the feel I want. Have you stayed in the B&B part? Is it the same experience? Do you know of any others in the region that are similar?

Any other pointers you guys can give me would be much appreciated - I've planned trips all throughout Europe, but for some reason this part of Italy is just overwhelming me. Maybe because it's the one I've been waiting to see for about 17 years now. I can't believe I'm actually going

Have you considered Montalcino or Montepulciano?

Or find a wine tour out of Florence so you can drink and not worry about driving.

TDudette those are both south of Siena - do you feel that is a better location than North? That's pat of my struggle given that I want to go to Florence and Pisa does it make sense to position myself further North or does it not really matter? many people seem to comment on romance south of Siena

They aren't that far...a bit over an hour. Montelcino came to mind about wine.

There is no such thing as "mass transit" in that part of the world. I assume that greg was simply trying to warn you that you cannot take a car into Firenze or Siena or Pisa or most other towns (or any city) unless you are a resident and have the required permit. Without one, you will get a hefty fine, which will arrive at your home address some months after your return from vacation and will have doubled or tripled in the interim. So stay out of towns and cities with your car.

No one can say if it's feasible to go to two small towns in a single day without knowing which two towns you are talking about. Get a map of Tuscany and plot distances and that should resolve that issue.

We spent several days in Tuscany in late August for my 70th birthday, so while that occasion is a LONG way from a honeymoon, I shared your wish for that movie version that I'd longed to see. We had some wonderful times, but I never did find the terrain I had envisioned, so I'll just tell you what I found in the areas we saw.

We stayed near Cortona; it's mountainous but looks out over the plains: beautiful in its own way but no rolling hills that I could find. On different days, we drove to Montepulciano, Pienza, Bagno Vignoni and Montisi. I enjoyed seeing them. We did discover that the switchbacks and mountainous terrain ate up your drive time and added a bit of stress. Each driver is different, of course, and we're getting old (!) but despite my planning, I had not taken those two factors into consideration. What looked do-able on the maps (and I bought the very detailed huge one, cut it up and just took the portion I knew we would need) was just too much in 102-degree heat with those driving conditions.

Final thing I hadn't realized was that the end of August meant that all the wheat fields in that area had been harvested and they were tan/brown. I hadn't expected that much bare ground. I couldn't change my birthday, and your honeymoon is set, but knowing all this I hope will help with your decision-making. What we did do that I LOVED was a hot air balloon ride. We took off near Montisi, but I know they're also available in other areas, perhaps over fewer barren fields in early September. And I loved Venice and Milan. I just hope to see other areas of Tuscany in a season when they're green.

Re: La Canonica di Cortine - Yes I have stayed in the B&B part and recommend it highly. We are staying in the Lucia Cottage this time but we stayed in the Torre Vecchio building on a previous occasion. The room was nice and the breakfast was very good. The B&B building is right in the middle of the other buildings that comprise the villa complex. You get the same feel, you just don't have a kitchen. It is a wonderful place. It seems to be out in the middle of nowhere but the town of San Donato in Poggio is a short distance away. There are some excellent restaurants nearby.

1) I suggest choose one of the towns that is not attacked by the hords until at least 10am each morning, so perhaps Buonconvento or San Quirico, both are real and small and pretty.
2) Or chose an agriturismo.it just out of town for some of the others, like Montepulicano or Pienza (most of which is actually flat so out of town does not mean "way down" a hill).
3) go real crazy and look at the agris outside of say St Gim (which is often empty in the evening after the coaches have gone and similarly nice up to about 9)
4) choose one of those towns that no one goes to. For instance Colle di val d'Elsa, which no one really goes to, but the old town is pretty old and has some wonderful old buildings, or Montopoli (old town) "but no one goes there Bilbo!" which has a beautiful green centre and just a couple of nice hotels., or Lucignano (where?) with most of its walls standing. In fact there are so many places to go to get away from everyone else it amazing that so many people ever go to Montepulciano.

oh yes, almost forgot
https://www.discovertuscany.com/tusc...lucignano.html
https://www.discovertuscany.com/coll...val-delsa.html
https://www.visittuscany.com/en/dest...-in-val-darno/

I recommend tripadvisor in europe it has not been completely destroyed by hackers and multiple votes for means something. September is not so hot that you need a pool, but you will want pretty things to wake up to.

I highly recommend San Quirico. It was a lovely little town with a few good restaurants to walk to in the evening. A typical hilltop, walled, one butcher, one baker type of village. It is also a great central location from which to wander to some of the towns and villages in the tuccant region like Montalcino, Montepulciano, Pienza, and Monticchiello. There are some nearby thermal springs and an upscale Spa in nearby Bagno Vignoni. We stayed in an apartment, but there is a very nice hotel in the town, Hotel Villa del Capitano.

I highly recommend San Quirico. It was a lovely little town with a few good restaurants to walk to in the evening. A typical hilltop, walled, one butcher, one baker type of village. It is also a great central location from which to wander to some of the towns and villages in the tuccany region like Montalcino, Montepulciano, Pienza, and Monticchiello. There are some nearby thermal springs and an upscale Spa in nearby Bagno Vignoni. We stayed in an apartment, but there is a very nice hotel in the town, Hotel Villa del Capitano.

Poggio Antico is a winery/vineyard just outside of Montalcino. They have beautiful vineyards, an informative tour, and some highly acclaimed Brunellos to sample or buy. They have an excellent restaurant where you can sit and have a nice meal overlooking their vineyards. I would recommend scheduling a tour there if you are in the area.

It's been a few years now, but my husband and I stayed in southern Tuscany for several days as part of a larger trip. We loved the Val d'Orcia area south of Siena. Absolutely gorgeous, though we were there in the spring when the hills were green; as opposed to the fall when everything will be browner after harvest as another poster mentioned. But we did love driving around, taking a peek at the tiniest hill towns (like Sant Angelo in Colle), and we also had a pre-booked tour and tasting at Poggio Antico that the poster above recommends. I think that if you commit a day to Florence, then pick up a rental car to visit Pisa quickly and then continue south, it won't be bad to drive a little further to get to the more scenice area south of Siena. Or I have never been, but I hear wonderful things about Lucca if you want to stay further north.

We did stay in the old town area of Pienza and enjoyed being right in town, but if I go back, I would also consider the villa stay out in the countryside. They both have their appeal!

If you click on my profile, you will see a link to my trip report where I describe our time in Tuscany (during the second half of our trip), and I tried to include a lot of info on how we came to make our decisions. Maybe it will be helpful to you. Congrats on your wedding and enjoy your honeymoon!

Thank you everyone - I think we have decided to stay south of Siena in Val D'Orcia region ish. You all have made it sound perfect! Just what we are looking for. We also are heading your car advice and headed to Florence by train, then Pisa and picking up a car there and heading south as to avoid any ZTL issues - don't need to start the marriage off with fines Assuming all these smaller towns don't have these types of zones correct? going to definitely book the Poggio Antico tour as well. I'm starting to breath easier and can't thank you all enough. Just have to focus on a hotel now - at least I have narrowed down the area.

Hotel Villa del Capitano is a bit confusing. Is it multiple buildings? It seems as though some rooms are very modern and others more rustic. Without a doubt I want rustic with great views. Any suggestions?

Again - THANK YOU everyone

I don't think you'll find any ZTLs but you will find a car park on the outskirts and very very limited access to some of them, so expect a lot of walking opps and take the right sort of shoes, cobbles ruin ankles in high heels.

We had no problems at all parking just outside the wall near our apartment. Some stairs up but not to much for my 60 year old knees. I don’t know much about Hotel Villa Del Capitano except that it was picturesque and looked like it would be a nice place for a honeymoon stay. There was a wonderful restaurant with terrace seating either there or next door. Our apartment a short walk away (Air BnB- owner Gavin, but too big for what y’all would want) was right across from the bakery and filled our place each morning with wonderful aromas. Be sure to visit Monticchiello and eat at Osteria La Porta, which is very near Montepulciano. If you look up Maitai Tom on Fodor’s, he stayed at Hotel Del Capitano on one of his trips to Italy and spoke highly of it.