If I told you to imagine Italy, then tell me about the first image that popped into your head, chances are, it would look like Tuscany. The amazing thing about Tuscany, though, is that it totally lives up to those picture-perfect postcard images. It’s a fantastically beautiful part of Italy, and I love it with all my heart. Ben and I have hopes and dreams of retiring to an Italian villa set in Tuscany someday. That’s how much we love it!
Rental Car Disaster
Our trip to Tuscany in the summer of 2022 did not get off to a great start. We had spent a couple days in Rome enjoying the sites, eating the good food, then planned to pick up our rental car in the late afternoon, and drive two hours north to a tiny hilltop town called Manciano just in time for dinner. We arrived at the rental car office around 4:00, where they gave us the bad news: they didn’t have a car for us.
Technically, I guess, they did have a car. But while I had booked an automatic car online (and not a cheap one either, mind you), they didn’t have any automatic cars left, only manual. Now, if you live anywhere besides America, you are probably thinking, “What’s the big deal?” but neither Ben not I can drive a car with manual transmission. Yeah, yeah, I know it’s not that hard, and I could learn if I put my mind to it. But I’ve never had to before. I just book automatic cars.
So here we are, stranded in Rome with no rental car, two hours away from the Airbnb where we are supposed to spend the night. Our whole itinerary for the next week in Tuscany depended on having a car, and things were not looking good. We called a few other rental agencies, but no one had any automatic cars available. Finally, we found one. We had to race across the city to make it to the rental office before it closed, and the car ended up costing a whopping 100 Euros a day! But hey, what are you going to do? Let this just be a lesson to always book a rental car in Europe way far in advance, and maybe to confirm your car a day or two before.
Thankfully, the rest of our trip to Tuscany was fabulous, and totally worth the stress and extra expense. Our first stop on the road trip was Saturnia.
Saturnia
If you have Instagram (which I’m assuming you probably do), you’ve likely seen pictures of these incredible hot springs.
The most famous thing to do in the Saturnia region is to visit the Cascate del Mulino hot springs. These hot springs have been in use since the Roman times, and are definitely famous for a reason! The water is warm and relaxing, with all those good mineral benefits you expect from hot springs. Based on reviews I’d read online, I anticipated that these hot springs would get really crowded really fast. So we showed up around 6:00 AM for an early morning soak, and had the place all to ourselves for about twenty minutes before other visitors started to trickle in. It was a truly magical way to spend the morning! (Even if it meant we smelled just a little bit like sulfur the rest of the day…)
Val d’Orcia
From Cascated del Mulino, we drove to the area of Tuscany that is often considered the most scenic. And pretty much the entirety of Tuscany looks like a painting, so that’s really saying something! My main goal while driving around this part of Tuscany was taking pictures of cypress trees and rolling hills. Well, mission accomplished! Most of these places are labelled on Google maps as “cypress road” or “cypress circle,” things like that. For the most famous photo spot in Tuscany, search for the viewpoint overlooking Agriturismo Baccoleno (that’s the winding road with the house and the trees).
I also highly recommend walking to Cappella Vitaleta from the “cypress road” viewpoint. I didn’t even know this little walking path existed until we pulled up to the parking area and saw a sign pointing towards the chapel. The walk was not long, but very pretty. When you reach Capella Vitaleta, don’t miss the café next door. We stopped by just for a coffee, but the owner was incredibly nice to us, and the views cannot be beat!
Most of these locations are roughly between the villages of Montalcino and Montepulciano, and if there’s one thing that can rival the Tuscan countryside, it’s Tuscan hilltop towns!
Pienza
If I could go back and change one thing about our trip, it would be to spend an entire day in Pienza. I didn’t think we’d need more than an hour or two to wander around this tiny town, but wow, it is awesome! The beautiful streets, the views, the shops, the church. It was all so picturesque, and this town just had a great vibe about it.
Make sure to stop just outside Pienza at Caseificio Cugusi Silvana, a cheese producer that makes a wide variety of pecorino cheeses. You can put together your own picnic basket of cheeses, cured meats, bread, and jams along with local wine. This is a prime setting for a picnic!
Montepulciano
Montepulciano is known for one thing: wine. This hilltop town is one of the most scenic in the area, and was surprisingly quiet on the day we visited. We weren’t entirely sure our little rental car was going to make it up those steep hills to the city, but the reward was worth the effort! Medieval buildings plus stellar views plus gelato plus wine. What more could we want? Most of the wineries in the area make use of underground cellars, many of which date back all the way to Etruscan times! The famous wine here is Vino Nobile, and we got to try it when we did a tasting and cellar tour at De’Ricci, one of the larger producers in the area. We loved our tasting and only wish we could have stayed longer to do some more!
Siena
Siena is one of the larger cities in Tuscany, but somehow even the cities in Tuscany are bursting with charm and history. The most famous sight in Siena is the Piazza del Campo, where a horse race is held twice a year in the city square. We did not time our trip right for seeing the horses, but the square itself is very beautiful. After exploring the Piazza, we went to the cathedral, which is supposed to be one of the most beautiful in Italy. While it’s hard to compare the churches in Italy, since they’re pretty much universally stunning, this one did stand out for its ornate stonework, and it’s well worth the small entrance fee.
San Gimignano
Our next stop was San Gimignano. Before we actually arrived at this hilltop town, we had an amazing multi-course lunch and wine tasting at Tenuta Torciano, a large vineyard that offers a ton of different packages. Our lunch included a number of local dishes, and we tasted ten different wines! While this is not exactly a quaint, local winery, sometimes bigger can be better, and we loved our experience here!
We stayed in an agriturismo just outside of San Gimignano called Casanova di Pescille, and I highly recommend it! We booked our say on Airbnb and were taken care of from the moment we arrived! I could seriously spend a week here, just lounging by the pool, taking in the views, and eating all the good food. (While it may be impossible to choose a favorite meal we had in Italy, the dinner we had our second night at Casanova di Pescille was definitely a contender!) An agriturismo is a farm or winery that doubles as a hotel, and you can find them all over Tuscany. You should absolutely spend a couple of nights at one of these agriturismos! It’s rural life meets luxury, and I am all here for it.
When we finally managed to pry ourselves away from Casanova di Pescille, we spent a day wandering around San Gimignano. This hilltop town is famous for its many tall towers, and is nicknames “the medieval Manhattan.” After walking along the medieval walls and admiring the views, we explored the town itself. I did a little shopping, and we got what may be the best gelato in Italy. The place is called Gelateria Dondoli. Get the champelmo. Actually, get all the flavors. I’m still dreaming about it!
Florence
The final stop on our road trip through Tuscany was Florence. Florence is its own beast, and after the slow-paced culture of the rest of Tuscany, getting back into city mode can be a shock to the system. I’m going to write a whole separate post about Florence, which you can read here for specific recommendations and suggestions, so for now, I’ll just say that while there are lots of great things about Florence, I suggest spending the bulk of your time in the Tuscan countryside, and just a day or two in the city.
Well, that’s it for our road trip through Tuscany, although I guess I should say first road trip through Tuscany, since we will definitely be back! I love Tuscany dearly, and can’t wait to go back and spend more time in this wonderful part of the world.
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