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From Florence to Val D'Orcia - "Best" Hill Towns?

Hi all! I'm planning my first trip to Italy in early April with a friend. We're doing a few days in Rome and Florence before renting a car and driving down through Tuscany from Florence to Rome (flying in and out of Rome). I'm super excited and also super combating FOMO, and at this point I'm trying to trim down the itinerary so we don't overextend ourselves. That's not la dolce vita! I wanted to get feedback and opinions from those who have visited Tuscany, especially on what hill towns and Tuscan villages are must-sees and which ones can be missed.

On our first day we're planning on driving from Florence to Siena with a couple of pit stops at wineries on the way, making another pit stop at San Gimignano and ending the day in Volterra (our Airbnb is nearby). I opted to skip Monteriggioni in favor of San Gimignano - is that the right move? Am I trying to pack in too much here? I suspect that I am, but... FOMO.

On the second day we'll drive down to Montalcino, Pienza, Montepulciano, and the thermal baths at Bagno Vignoni before settling into our Airbnb nearby for the night. Of those three towns, how would you rank them from must-see to can-skip? Are there other villages in the area that we should consider instead? What wineries thereabouts are worth visiting? It's only about 3 hours of driving between all points (according to Google maps) as there's not a lot of ground to cover.

We don't plan on visiting any of the museums or anything at the towns, just walking around and sort of getting a feel for the places. I'm aware it's a bit of a whirlwind tour through Tuscany and we won't get a deep dive into any of the places we visit, which is fine by me for this trip. Still, any advice or a hard dose of reality from more seasoned travelers would be greatly appreciated!

Posted by
3078 posts

How much time on the ground (nights) do you have? Just an FYI, driving after an international flight is not recommended.

Are you aware of italys driving rules?

Posted by
4 posts

We'll have three nights in Tuscany, one of which will be spent further south near Rome as we need to return the car on the early side in the morning. We have our Airbnbs booked already so the general direction and pace of the drive is set.

We are aware of the driving rules in Italy; my friend will be behind the wheel for the duration of the trip.

Posted by
4 posts

Jean - your report was so interesting! I've never taken a solo trip as travel is such a social and shared experience for me, and I really enjoy showing my travel companions around. Still, I'm not opposed to the idea of doing it one day! I'm also an insane planner - our itinerary is just about finished and the trip isn't for two more months! But I love it.

I'm glad to see you liked Montepulciano and Pienza. Right now out of the three Montalcino is at the bottom of the pile for me and may need to be sacrificed so we can spend a little more time in the other two towns and not feel rushed. Originally I had us going to Lucca on the first day, but had to cut it. Another time, I'm sure!

Posted by
1021 posts

Our favorites were Montepulciano and Pienza
Did visit Montalcino but could have easily skipped
Enjoyed the drive to Bagno Vignoni
Also did a quick stop in San Quirico

I would stay in just 1 place for all those towns, no need to change hotels each night
Everything is very close

Posted by
124 posts

I've been to all three towns, and I'll discuss them below, but first to your other questions. I can't think of any other villages in that specific area that are worth visiting. I think if you try to do all three towns and Bagno Vignoni, you're going to have quite a full day, so I wouldn't try to add anything else. We actually did a modified version of the RS "heart of tuscany" drive, which I'm assuming you're modeling your own drive off of (at least it seems that way, based on the towns you mention) and then combined/modified the Crete Sensei Drive with some of the Brunello Wine Country drive for a second day. It occupied our time well. The restaurant RS recommends for that drive is a good one.

Pienza was my personal favorite. It was so quaint and sweet with the flower pot decorations everywhere. We had some of the best gelato of a three week Italy trip there as well. We were there relatively late in an afternoon, when a solid amount of tourists had cleared off, which I think played into our love of it, but I really enjoyed walking the main street and window shopping. There are some fascinating stalls on offer.

Montepulciano is very nice as well. They have a little bus tour thing that gets you up the hill (it's a steep hill) that connects basically all the main sites in town (main square, church, ect) that we found worthwhile to pay for. Definitely check out at least one wine cave.

If you're going to skip one, I'd skip Montalcino. It's effectively a home base for going out to the various wineries in the area (or buying wine, if you can't get out to the wineries) and doesn't have the same quaintness of the other two towns. The castle/fort is at least cool to look at, and there is some great overlooks to the countryside but otherwise, it didn't feel like there was that much to the town. However, if you can fit in San Altimo somehow, which is near's so freaking beautiful there. I liked it better than the other Abbey RS mentions in the area, though both are worthwhile stops.

I can't speak to many of the wineries in the area but if you want to go on a tour, I'm sure any of the RS ones are fine. We toured Altesino Winery, which is located between Montalcino and Siena, late afternoon. I really enjoyed the tour and the (slightly overpriced but whatever, we didn't really care) wine tasting and bought some wine there as well.. Just make sure, if you decide to do a winery, that you call/reserve in advance. A decent amount of the wineries in the region aren't super keen on people just showing up.

Posted by
2884 posts

Tealeaves, glad you enjoyed the trip report. I had so much fun on the solo trip but also enjoy traveling with my husband. This year will be the best of both - I’m going to France for two weeks, and he will join me for the third week.

Don’t miss the gelato at Buon Gusto in Pienza! Have a great time in Italy!

Posted by
269 posts

Sounds like you're returning your car in Rome. If so, you'll likely drive past Orvieto on your way there; it's well worth a half-day stop on the road.

Posted by
2716 posts

One red flag jumps out at me ; I.e., wine tasting while on country drives. In general, European legal limits on blood alcohol levels are lower than those in U.S. and rather strictly enforced. I believe this is true of Italy. Roads in Tuscany tend to be narrow and winding, demanding unimpaired driving skill. In addition, the Italian police are known to set up random check points. We’ve been pulled over twice. One time, in the Alto Adige, it seemed they were looking for stolen cars. However, with no English on one side and no Italian on the other, it was hard to tell. The other time was in Tuscany, and they did check my license and my idp.*. You should consider a wine tasting tour so you can taste without worry.

I’ll add my vote for Pienza.

*. Don’t let anyone talk you into not getting this. It takes a few minutes and around $20 at a AAA office. Just because some people have never been asked for it doesn’t mean you won’t be.

Posted by
143 posts

I agree with the posters above: we really enjoyed Pienza and Montepulciano. If you don't have time, you can skip Montalcino. We also enjoyed an afternoon at Bagno Vignoni. But to confuse you more, my mother's favorites were Lucca and Siena.

Posted by
1389 posts

On our first day we're planning on driving from Florence to Siena with a couple of pit stops at wineries on the way, making another pit stop at San Gimignano and ending the day in Volterra (our Airbnb is nearby). I opted to skip Monteriggioni in favor of San Gimignano - is that the right move? Am I trying to pack in too much here?

Yes! I don't see where you are adding the time it will take to rent the car and head out of Florence. We stayed in Greve near Florence and took a day trip to San Gimignano and Volterra. Just those two were a full day I would have wished to have a full day for both.

Trying to see them, Siena and stop at wineries is way, way too much.

It's a shame you are locked in to your accommodations. We spent the entire week at the same agriturismo, taking day trips from that central location. We ranged from Florence in the North and south of Asciano in the south.

Posted by
4 posts

I wanted to stop in and thank everyone for their feedback and input, and give an update on our trip!

Y'all were right, and it was as I suspected - I was trying to pack in far too much during our three days in Tuscany! Despite Google maps telling us that it would only take so long to drive between points of interest, in reality it took us much longer. I'm not sure if the maps didn't take into consideration the speed that had to be considered on the narrow, winding roads, or where the disconnect was, but the time we actively spent on the road was longer than anticipated so we had to forego several stops.

On the first day we picked up our rental car in Florence and drove down towards Siena. We stopped at the Castello di Ama winery for a tasting, which I would highly recommend doing, and also at Barolo Ricasoli, which I didn't enjoy as much. We just stopped in for a tasting, though, so I'm sure a full winery tour would have been much more enjoyable. We ended up having to skip Siena and instead stopped by San Gimignano to walk around for a bit before heading to our agriturismo in Radicondoli.

On the second day we left our agriturismo and headed towards Pienza. We made a pit stop at San Quirico d'Orcia for lunch, unplanned, and had an absolutely stunning meal there. Totally worth going off-book for that. Stopped in Pienza, then Montepulciano, which was my absolute favorite. I would have loved to spend more time there. We visited Enoteca Contucci and bought some wine. Our agriturismo that night was very close to Bagno Vignoni, so we drove out there as the sun was setting. It was so lovely.

On the third day I actually ended up being super ill, so we had to skip most of our planned stops in favor of a trip to the hospital. We did stop at Sant'Antimo abbey, which I adored and wished I had felt well enough to explore more. We also had to skip the Terme di Saturnia thermal baths, which is probably my biggest regret of the trip. We were meant to drop off the car in Rome the following morning, so we just drove through the countryside to our last Airbnb in Trevignano Romano near Rome. It was on a lake and an absolutely gorgeous setting. I would gladly stay there again.

And that was our sojourn to Tuscany! Thanks again to everyone for their help. I'm already dreaming of my next visit.