4 Stunning Hill Towns You Should Visit in Tuscany

August 11, 2023

With picturesque landscapes of vineyards and Italian cypress trees peppered over its rolling hills, Tuscany is one of the most beautiful regions in Italy. Driving through the Tuscan countryside, you'll encounter many medieval towns gracing the hilltops. In this post, I'll recommend four beautiful hill towns that I don't think you should miss on your visit to Tuscany. During your visit, admire the architecture, taste the local wine, and soak in the historic feel of these charming towns and you won't regret it!


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Tuscany Highlights

Located in central Italy, Tuscany (Toscana in Italian) is well-known around the world for its beautiful landscapes and rich culture. As the birthplace of the Italian Renaissance, it was home to many influential figures in literature, art, and science.  

Montepulciano architecture

In Tuscany's magnificent capital city, Florence (or Firenze in Italian), you'll see signs of this prominence in Italian history. But driving around the countryside and staying in a Tuscan hill town, you'll find a slower pace of life.

As you walk around Tuscany's medieval hill towns, you'll be charmed by the historic feel and beautiful architecture. From the old city walls and fortresses, admire panoramic views of Tuscany's beautiful valleys. Stop at various wineries and wine shops to try out the local vintages, and perhaps purchase bottles to take back to your accommodations. And relax for a delicious meal and a refreshing gelato along your journey. Tuscany's hill towns have so much to offer that you'll want to return to the region multiple times to visit more of these beautiful villages.

Getting to Tuscany

The best way to reach the hill towns in Tuscany is to either fly or take the train to Florence, then rent a car. Since these towns are not accessible by train, renting a car is really the best way to see them. 

Buses do run to some of the Tuscan hill towns, but I read that they aren't always that reliable. Since I did not try to use them, I can't offer my own thoughts on them.

Renting a Car in Florence

The easiest place to pick up a rental car in Florence is at the airport, which is about 5 km outside of downtown Florence. To get there, just take the tramway from Santa Maria Novella Station. Once you pick up the car, it's easy to hop on the highway towards the countryside. 

Booking a Rental Car: To start searching for rental cars, I used Rental Cars to compare prices. Once I found a deal, I booked online with Avis Rental Cars.

Alternatively, you could pick up the rental car at a downtown office in Florence. This option may be more convenient, but is also riskier for accidentally driving on a restricted street if you take a wrong turn and incurring hefty fines. Also, on Sundays the downtown offices have reduced hours. (You can read more about our drama with this at the end of my Florence post.)

Pro Tip: If you do not have an Italian or EU driver's license, you are required by law to have an International Driver's Permit (IDP) in addition to your driver's license to drive in Italy. If you live in the U.S., it's quick and easy to get an IDP at AAA

Tours to Tuscany

If you do not feel comfortable driving in a foreign country, you could book a group tour. Booking a tour like the ones below, all the details are arranged for you, so you can enjoy the sights. 

Visiting Hill Towns in Tuscany

In our Italy itinerary, we had 2.5 days to spend in Tuscany.  During that time, we visited four beautiful hill towns - Siena, Montalcino, Montepulciano, and Pienza - which I think are worth a visit when you're in Tuscany. In this section, I'll share some of the highlights of these lovely towns.

As with many of the stops on our Italy itinerary, the time we spent in Tuscany was enough to get a taste, but left us wanting more. You could easy spend a week (or longer) exploring the various hill towns. 

Pro Tip: When planning your route through Tuscany, remember to factor in driving time between towns. Especially if you want to plan to head to towns in nearby regions, like Umbria or Lazio.

We stayed for one night in Siena and 2 nights in Montalcino which helped us to get a better feel for each of those beautiful towns. Plus, staying further south in Montalcino cut down on driving time during the day we visited Montepulciano and Pienza.


Siena, one of Italy's most beautiful medieval towns, is known worldwide for the Palio - a horse race which takes place in the Piazza del Campo, aka 'Il Campo', the city's main square.

An important city during medieval times, Siena's historic center was designated a UNESCO World Heritage Site. Wandering around the city, you'll be in awe of the beautiful architecture, charming alleyways, and overall medieval feel to the town. 

Street in Siena

Palio di Siena - Competitions are Fierce

If you love horse racing and plan far in advance, visiting Siena during the Palio would be an exciting time. Each year the Palio takes place on July 2 and August 16 in the Piazza del Campo. During this race, the city's contrade (districts) compete against each other with much fanfare. 

Contrade are a legacy from medieval times in which the city was divided into various districts. Today, Siena has 17 contrade and each contrada has its own emblem and flag. You'll notice these flags and also the mascots as you walk around the town.

Panther contrada statue in Siena

Everyone in the town belongs to a contrada from birth, so you can imagine the rivalries which come out during the Palio. Since the race is such a popular event, I image you need to book far in advance if you'd like to visit the city during this time.

Want to learn more about the Palio? Check out the Discover Tuscany website.

Piazza del Campo

One of Siena's unique features is its main square - the Piazza del Campo - where the Palio takes place. Unlike many other town squares, you can very easily see how this one is used for a horse race. Surrounded by cafes, it's the social hub of Siena and is a great spot to grab an aperitivo and admire the view.

Aperitivo in Piazza del Campo in Siena

Palazzo Pubblico

At the southern end of the Piazza del Campo, the 14th-century Palazzo Pubblico (town hall) sits as a representation of civic life in Siena. Throughout history, the Palazzo Pubblico has been home to the city's administration.

Piazza del Campo Siena

Inside, the rooms of the palace are lined with frescoes commissioned by the government, many of which are secular in nature. You can get taste for the palace's interior by visiting the Museo Civico - Siena's city museum - on the first floor of the Palazzo Pubblico. And, if you are up for a workout, you can climb the Torre del Mangia - to get beautiful views of the city.

Unfortunately, I did not have a chance to visit the Palazzo Pubblico or climb the tower on our visit. Perhaps something for a future visit!

Duomo di Siena

Siena's magnificent cathedral - Cathedral of Santa Maria Assunta - is one of my favorite cathedrals that we saw in Italy and one reason I think you have to visit Siena on your trip to Tuscany.

Duomo di Siena

Constructed primarily over the 13th and 14th centuries, the intricate marble façade is matched by the splendor of the interior. This cannot be said for all of the cathedrals we saw on our trip.

The intricacy of the sculptures, pulpit, and frescos in the Duomo di Siena are stunning. 

Siena Cathedral interior
Duomo di Siena - dome and columns
Marble tiles in Siena Cathedral
Altar in Siena Cathedral

During the peak months, you'll have to pay to enter the cathedral. It's worth arriving early to buy tickets. Since we had limited time, we bought the pass which included the Piccolomini Library, but skipped out on the full pass which also gave access to the crypt and tower.

Piccolomini Library

I highly recommend visiting the Piccolomini Library as the frescos by Pinturicchio were breathtaking. The photo below does not fully capture just how crisp and intricate the frescos are.

Piccolomini Library

Getting to Siena

After picking up our rental car at the Florence Airport, we drove straight to Siena which took ~1 hour to reach. 

Siena Accommodations

As I mentioned, we spent one night in Siena during our trip. Siena is one of the larger hill towns in Tuscany and has many accommodations from which to choose.

We stayed at the Athena Hotel, a 4-star hotel at the edge of town with a convenient parking lot. Our room was comfortable and it was an easy ~10-minute walk to the Piazza del Campo from the hotel.

Athena Hotel room
Athena Hotel view

The Athena also has a parking garage beneath the hotel which was perfect for us. As always in Europe, the garage is a tight squeeze so only rent a car that's as big as you need to make sure you can fit into smaller spaces. 


If you love big, bold red wines, then a stop in Montalcino to taste the delicious Brunello di Montalcino is a must while you're in Tuscany. This small medieval hill town was fairly quiet and is compact and easy to walk around, albeit with a bit of climbing. It's a great place to relax for a few hours or to use as your base to explore Tuscany.

Tuscany featured image Montalcino

Fortress of Montalcino

Perhaps the most impressive and notable sight in Montalcino is the Fortezza di Montalcino or Montalcino Fortress. Built in 1361, it remains mostly intact today and has an impressive view of the Val d'Orcia.

Fortezza di Montalcino

There is also a wine shop inside the fortress where you can taste and purchase some of the exquisite Brunello di Montalcino wines as well as others from the region.

Pro Tip: Head to the western side of the fortress just before sunset to appreciate the magnificent views as the sun sets over the valley and nearby hills.

Sunset in Montalcino

Where to Stay in Montalcino

If you're visiting Tuscany for multiple days, I recommend Montalcino as a peaceful town in which to stay. We stayed in a lovely bed and breakfast on the Montalcino hillside called B&B Porta Castellana.

Our host was friendly and so helpful in recommending places to go and helped us get our rental car to the B&B when we got terribly lost. The property is a short (but steep) walk down from the center of Montalcino so it's easy to go into town for dinner. The garden setting is peaceful and the perfect place to eat breakfast. 

B&B Porta Castellana room
B&B Porta Castellana breakfast

Where to Eat in Montalcino

Since we stayed in Montalcino for 2 nights, we got to try several of the restaurants in the town. I'd recommend the following places for a delicious meal: 

  • Enoteca Di Piazza: We had a late lunch and a couple glasses of delicious Brunello di Montalcino wine here. Highly recommend the truffle pasta.
  • Ristorante Trattoria L’Angolo: Dining on the streets of Montalcino soaking in the history, the food and wine were delicious and the atmosphere couldn't be beat.
  • Vineria Le Potazzine: Another fantastic spot with alfresco dining and a delicious risotto.
Brunello di Montalcino wine
Truffle cream pasta


Perched high on a ridge, Montepulciano is a beautiful medieval town that will potentially involve a workout to reach it depending on where you park. As you drive up to the town, you'll encounter several parking lots. Obviously, the lower you park, the more of a climb up you'll have to reach the town. 

View of Montepulciano hill town in Tuscany

Once you reach the town, wander through the charming alleyways, try the Vino Nobile wine, and admire the spectacular views of the Val di Chiana and Val d'Orcia.

View from Montepulciano

Piazza Grande

The main square of Montepulciano - Piazza Grande - is the highest point in the town. If you've seen the Twilight movies, then this square and in particular the Palazzo Comunale (town hall) should look familiar. The crowd scene from the New Moon film that took place in Volterra in the story was actually filmed in Montepulciano instead.

Piazza Grande in Montepulciano

Duomo di Montepulciano

Montepulciano's cathedral - Santa Maria Assunta - is the main place of Catholic worship in the town. Built in the 16th century, its façade is still unfinished. The interior is stark as well but has several artworks that you can admire.

Duomo di Montepulciano
Montepulciano cathedral interior

Fortress of Montepulciano 

The fortress of Montepulciano is a military fort that was original built in 1261 but has been destroyed and rebuilt several times. Today, it serves as a venue for exhibitions and events and has beautifully-manicured gardens.

Gardens at Fortress in Montepulciano

The fortress is also home to the Consorzio Del Vino Nobile di Montepulciano and its wine shop. At the wine shop, you can taste over 100 labels of the Vino Nobile wine. At the shop, you receive a card which you swipe to pour a taste from the bottle of your choice. While trying to decide which wines to sample, admire the archaeological ruins under your feet through the glass floor.

Wine shop in Montepulciano

The wine shop also serves small bites and has a beautiful terrace with panoramic valley views where you can enjoy your tastings. 


Situated between the Montalcino and Montepulciano, Pienza was the hometown of Pope Pius II. In the mid-15th century, the Pope began transforming his small home village into a beautiful Renaissance town. In 1996, Pienza was declared a UNESCO World Heritage site.

Street in Pienza

Pienza is a lovely town to wander around and admire the beautiful architecture, especially the Piazza Pio II (main square) and the Duomo (Pienza's cathedral). It's fairly flat compared to most of the hill towns but does get crowded, especially on weekends. 

Piazza Pio II in Pienza Italy
Duomo di Pienza

What We Missed - Staying in an Agriturismo

Despite having a delicious taste of Tuscany, we did miss out on one experience in particular that I would have liked to try, which is to stay at an agriturismo.  An agriturismo is typically an independently-owned active farm or agricultural operation which also welcomes guests to stay on the property. You can find these all over Italy, not just in Tuscany.

There is a huge variation in the type of agriturismo you can book - from what type of farm it is, to the level of luxury and what is included in the package. Some stays include farm-to-table meals and wine produced on the farm in their prices. Some have swimming pool and air-conditioning while others are very basic accommodations. 

Book Your Agriturismo Early

Especially during peak tourist season, these agriturismi (plural of agriturismo) book up early. As a result, we were not able to stay in one for our last trip. If you'd like this experience, I'd recommend booking very early or visiting during an off-peak season.

Final Thoughts

Driving through Tuscany's undulating hills and stopping at its medieval hill towns to admire the architecture and sample the delicious local wine was a highlight of our trip to Italy. Although I'd highly recommend seeing these four hill towns on your trip to Tuscany, there are many more to discover as well. 

Let me know what other hill towns in Tuscany, or other regions, you'd recommend visiting on a trip to Italy!

Happy travels!

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4 Stunning Hill Towns You Should Visit in Tuscany
4 Stunning Hill Towns to Visit in Tuscany Italy
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