Walking away from Siena’s gorgeous cathedral, with its black and white marble facade set against a cobalt blue sky, I’m excited to be headed somewhere even more impressive. I turn into a narrow side street and then walk through a nondescript doorway. The rich, deep colours immediately grab my attention and I know the silky smooth texture is what draws the crowds.
Thanks to a tip-off from a local, I find myself in gelato heaven at La Vecchia Latteria; my number one reason to visit Siena. Not really, but kind of.
Aside from a few short trips I’ve mostly avoided Italy’s most famous region. Tuscany is the Italy so many dream of, with its beautiful hilltop towns, gorgeous architecture, rolling hills and of course all that mouthwatering food.
It’s what I think of when I dream of Italy too but my aversion to crowds has always held me back. I have avoided Tuscany in lieu of quieter Italian regions Umbria and Puglia or more often, quieter European destinations like Slovenia and Albania.
But seeing as I happened to be driving through Italy in May, a time of the year when there are fewer tourists yet perfect weather, I figured I’d take advantage of the opportunity and take my first road trip through Tuscany.
Wanting to get the most out of the trip I stopped at as many towns as possible but it’s an exhausting way to travel. I think it’s best to savour three or four towns and then finish up in Florence, an essential stop on any visit to Tuscany. Bagnoregio and Orvieto are just outside of Tuscany but definitely worth including in this trip.
Tuscany Road Trip
If you pay attention, you might notice that not all of these destinations are in Tuscany. I’ve included stops in nearby regions Lazio and Umbria. The reason for this is simply that they’re close and if like me, you start your trip in Rome, then you’ll be starting in Lazio.
Civita di Bagnoregio
Walking along the steep concrete path up to Civita de Bagnoregio I was curious as to how it might have looked in the past, hundreds or even thousands of years ago when it was first settled. It must have been quite a feat to reach the isolated island-like cliff which juts up sharply from the valley below.
But now it’s easy as you can park your car at the base of the bridge and walk directly through the weathered gate and into the village, home to around 12 residents and an adorable tribe of lazy cats.
It takes around five minutes to walk from one end of the town to the other, even when stopping to take in the views over the river valley. The restored old town is quaint but there isn’t much to do as such. But that’s fine, it’s not about that.
The highlight is viewing the town from afar, looking up to the houses teetering on the edge of the cliff, hoping they won’t topple down the valley during the next earthquake. Unfortunately, this is a real risk.
Civita de Bagnoregio to Orvieto takes you from the region of Lazio to Umbria. Orvieto is the birthplace of chicken cacciatore and home to one of the most beautiful cathedrals in the world. The Duomo dates from 1290 and you’ll see a steady stream of people coming in and out over a short period of time.
Orvieto is home to some truly incredible restaurants. I tried a couple of places right in the centre and everything was incredibly delicious but expensive of course.
The reduce car traffic and the resulting noise and air pollution, I suggest leaving your car at the base of the hill and taking the cable car or escalator up to the main town centre.
Unlike Civita de Bagnoregio, once you reach hilltop Pienza you’ll see there is much to explore in every direction, admiring the crowded palaces and squares as you go.
In Pienza, you’re finally in the Tuscany region of Italy.
Pienza’s streets are crammed with restaurants and little shops selling some of the most delicious food in Tuscany, especially the pecorino cheese the city is known for. Most of the shops offer tastings which I suggest you take advantage of as the aged cheeses have a completely different flavour to the less mature varieties.
Other local specialities include wine (of course), dried herbs, porcini mushrooms and pici pasta served with cacio e pepe.
If you don’t want to eat in crowded Pienza, there are several agriturismo just outside of the city where you can lunch in the Tuscan hills. Follow the signs to any you see, you can’t really go wrong.
While one of the best ice creams in Italy is a great reason to visit Siena, it’s not the only one. Siena has long been one of my dream destinations which thankfully lived up to the hype.
Siena is much larger than Pienza so there’s plenty to keep you occupied if you plan on staying a few days, even if those things mostly consist of eating and drinking.
As always when travelling, I think the best thing to do is wander the back streets until you get lost, eat in a quiet restaurant away from the touristy centre, then make your way back to see the main sights.
As you explore you won’t be able to miss the Torre del Mangia on Piazza del Campo, the centre and main attraction in Siena. The Palio de Siena horse race is held here twice a year, in July and August. Thousands of spectators descend upon the square for a 90-second race. Sounds like another reason to visit in May instead of peak summer.
Like most horse races, this is a difficult event for the animals. I suggest avoiding it and supporting sustainable tourism alternatives.
Along with all the usual delicious Tuscan fare and chianti wine, Siena’s signature dish is pappardelle with wild boar. You’ll find it on just about every menu in Siena. Now though, you can easily find vegetarian or vegan pappardelle alternatives if you prefer.
I skipped the meat but did visit the city’s other major attraction, Siena Cathedral. It reminds me in some ways of the Duomo in Florence but also of Orvieto Cathedral in Umbria.
Another day in Tuscany, another hilltop town. San Gimignano was more to my liking as it’s famous for white wine, Vernaccia de San Gimignano, instead of the red chianti typically found in Tuscany.
The hills surrounding San Gimignano are covered with vineyards that produce the delicate, fruity wine, one of my favourite wines in the world.
Some shops offer tastings but I suggest trying a glass or two at one of the wine bars around town so you can sample some local food at the same time.
Be sure to respect Italian law and don’t drink and drive.
Florence is one huge open-air museum. The gorgeous cathedrals, towers, bridges, squares, fountains, statues and atmosphere are free to enjoy as you meander around the city.
You can rush around and see the highlights in one day but for first-time visitors, I think four or five days is the better way to go. Take it slow and savour the experience.
This will give you plenty of time to visit the many, many museums while tasting as much Tuscan cuisine as possible.
If you have more time, here are some other hilltop towns you might want to add to your road trip itinerary:
While driving from Civita di Bagnoregio to Florence is a great way to see central Italy’s highlights, it might be more relaxing to base yourself in one city for a couple of weeks, taking day trips around the countryside.
If that’s you’re preferred way of travel I suggest staying in Siena for its central location and to maximise your foodie options.
I recommend staying at I Merli di Ada as this is one of the more sustainable hotels in Siena. Another option is to find a central agriturismo which is an Italian bed and breakfast style accommodation, often situated on a working farm.
This hilltop road trip would also make a great winter road trip, especially if you like to travel off-season to avoid crowds where possible.