Tuscany and wine are the perfect pairing. The Tuscany region of Italy, located north of Rome is home to some of the country’s best wines and most beautiful views. Tuscany is known for its rolling hills, its vibrant cultural cities, its picturesque hilltop towns, and for the food and wine that people flock here for. When planning your trip, it can be hard to figure out where to go in Tuscany, but I’ll fill you in on the best Tuscan villages to visit for a day-trip from Rome.
I mean, who doesn’t love sitting in paradise drinking wine and eating delicious food?
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The best Tuscan villages to visit are:
- Montalcino for its charming medieval fortress walls and famous wine
- Pienza for its Renaissance history and stunning views
- Montepulciano for its noble past and medieval city centre
But before we dive into the best places to visit in Tuscany, it’s important to understand the region as a whole.
The Tuscan region is divided into nine provinces and the city of Florence. The province of Siena is the second largest, and that’s where you will find the best towns to dig into Tuscan wine and culture.
With the city of Siena as the province’s capital, the region has 34 other comuni – or towns. The region also produces some of the country’s best wines – Chanti, Vino Nobile di Montepulciano and Brunello di Montalcino.
Cutting through the heart of the region is the UNESCO World Heritage landscape of Val d’Orcia, which according to UNESCO, the reason for its inscription is that the region “is an exceptional reflection of the way the landscape was re-written in Renaissance times to reflect the ideals of good governance and to create an aesthetically pleasing picture.”
Basically, Italy has protected this area because of its importance to the artistic culture of the Renaissance. Who can argue with that?
How much time do you need?
The question of how much time you need to visit Tuscany can be tricky. First, it really depends on your travel style. If you are a go-getter, then spending one day visiting the best Tuscan villages is enough.
But if you want to take your time and visit different wineries and stay in some of these beautiful hilltop towns, then you can spend as much time here are you like. I mean, who doesn’t love to fill up on tasty wine in the most beautiful region of Italy?
The best Tuscan villages to visit, Montalcino, Pienza and Montepulciano, can all be seen in a day trip from Rome.
How to get there?
There are many ways that you could travel to these Tuscan villages.
The first option is through a tour. This tour from City Wonders is the one that I took. I didn’t want to rent a car in Italy, and with my short timeline in the country, I did small day trips from an apartment in Rome. This tour takes you to every stop I mention here, including a lovely lunch and wine tasting just outside of Montalcino.
The second option is to drive. The three towns are within an hour’s drive, and the region is only 2.5 hours from Rome. This can easily be done as a day trip from Rome at your leisure. It also means you are not tied down to a bus with other people.
The third option is to use transit. While it would be significantly cheaper to use the mix of train and bus that is available to get to each Tuscan town, about $50 to $100 CAD, you are faced with longer travel times. This means you either travel for 11 hours, only visiting each town for 1.8975046 milliseconds, or you make it a multi-day trip.
How much will a Tuscan trip cost?
Again, this will depend on how you spend your time in this Tuscan region.
The City Wonders tour costs less than $200 CAD per person, which includes your transportation, food and wine tasting, any entrance fees and a guide. Renting a car for the day in Rome can cost you anywhere from $60 to $180 CAD, depending on your preference for wheels.
You’ll also want to bring some spending money to buy the wine if you like it; each bottle ranges from 10 to 50 Euros. And you can’t miss buying some of the most delicious cheese and meats in Montepulciano and the best gelato IN THE WORLD in Pienza.
First stop: Montalcino
Montalcino is the smallest of the three Tuscan towns I’m going to introduce you to, but it’s likely the most famous. That has to do with the wine produced here, Brunello di Montalcino.
Before I get into what the town is like today, I want to explain some of its history. During the takeover of Siena province by the famous Florentine Medici family, this medieval town held steady for years, refusing to relent. It’s a feisty hilltop village that dates back to the 9th century when the first mention of it was documented.
Montalcino is most known for its prestigious wine, Brunello di Montalcino, or Brunello for short. This wine, according to the lovely family who owns the vineyards I visited, is made with 100% Sangiovese grapes grown in the area.
It was the first wine to be awarded the Denominazione di Origine Controllata e Garantita status, the highest level and most restrictive quality assurance label given to Italian wine. The label denoted that the wine was produced in a specific region using specific methods and meet a specific quality standard. Italians don’t mess around with their wine.
The Brunello must be aged five years before being allowed to be sold. Which, I mean, is supposed to be better? I’m not a wine connoisseur at all. I just swirl it around, give it a good sniff and say, “Smells like a red!” I digress. Those who do love wine will note that a Brunello is “smooth with a medium finish with tasting notes of tobacco, fig and leather.” And that is a direct quote from my parents, who are in fact level 2 wine snobs. (Love you if you’re reading this!)
What to see in Montalcino
Abbey of Sant’Antimo
Of all the churches I stepped foot into in Italy, The Abbey of Sant’Antimo was my favourite. The incredible architecture may seem simple compared to the grandeur of larger churches like St. Peter’s Basilica in Rome and St. Mark’s Basilica in Venice. But it is no less striking.
Set among the hills of the Val d’Orcia and outside the city of Montalcino, the abbey is a popular stop for visitors. The patrons of the abbey sell olive oil and perfumes made right there on the grounds. But the origin story of the church is was is genuinely fascinating.
The earliest mention of the land dates back to the 800s AD, but the church itself was officially opened in 1118 AD. The legend goes that the Roman emperor at the time, Carlo Magno, found refuge here from the plague decimating Rome. To give thanks, he founded the abbey.
The church fell into disrepair over the centuries until the Italian state brought it back to life in the 1870s.
Sagra del Tordo
If you feel like you’re not getting enough medieval culture while travelling to Tuscany, then you have to stay for the Sagra del Tordo. The festival transports you back in time to the Medieval Ages with historical reenactments, traditional food and, of course, Brunello wine.
Usually, the last weekend in October, the whole town of Montalcino gets into it, with flags, costumes, feasts and games.
Fortezza di Montalcino
The fortress walls that surround the hilltop town were built in the 1300s and defended its citizens for hundreds of years. When the Florentine Medici family came a’knockin in the 1500s, the walls helped the town resist the conquest. Today, you can explore the courtyard and climb the walls to look out over the Val d’Orcia. You can even do a wine tasting right there in the fortress.
Wine Tasting in Tuscany
“I detect notes of grape” – me, on a wine tasting.
While I might not be a connoisseur of wine, I know a good experience when I, well, experience it. At Poggio il Castellare, I was – as they say – wined and dined.
The Vineyard is located about 10 minutes south of Montalcino on an acreage right in the heart of the Tuscan hills. The estate and cellars are made of stone in the classic Tuscan style and are surrounded by rows upon rows of grape vines.
During the summer, you can dine al fresco in the covered outdoor dining area. During the cooler months, the wine cellar is transformed into a dining experience.
You might also like: The best all-female Tuscan winery you’ve never heard of.
We were treated to a three-course lunch paired with four wines made right there on the property, including a Brunello. We finished off with a splash of Grappa, a type of grape-based liquor made from all the remnants of wine-making, like skins, pulp, seeds and stems.
If you’re going to drink wine, then it is worth going wine tasting in Tuscany. Experience the bold flavours and sip the history of wine in the region, while taking in the majestic views.
Second stop: Pienza
If you’re looking for the best Tuscan villages to visit, then look no further than Pienza. This hilltop town is one of the most well-known in the area.
Pienza was the summer home of Pope Pius II, where he transformed his hometown into a Renaissance village after he became pope. Then he totally named it after himself, because why not?
The town has remained relatively unchanged since it was recreated in the 1400s, which is why it has been designated a UNESCO World Heritage Site.
I’ll try to express how perfect Pieza is. It indeed was one of the most magical places I visited in Italy. Pienza is everything I imagined about Italy all wrapped up in a cobblestone street, rustic shutters on the window, flower boxes giving of sensual aromas, little mom and pop shops, and the stunning views of Italy’s UNESCO World Heritage landscape Val d’Orcia.
It’s neat because Pope Pius II wanted to transform the town he was born in into the ideal Renaissance town, and now centuries later I was moved to tears over the beauty of it.
Picture standing in the middle of Piazza Pius II, the central square. In front of you is a church, behind you are little shops. In the corner of your eye is a fountain and you momentarily let your mind wander. The soft sound of a violin reaches your ear. You’ve heard the tune before but can’t place it. As you head closer to the source of the music, you wander into the Palazzo Piccolomini di Pienza, the principal residence in Pienza now a museum of sorts.
The song is What is a Youth and is the popular song from the 1968 movie of Romeo and Juliet, which was filmed entirely in Pienza.
Here’s a lovely cover of the song:
I’m not kidding, it was so beautiful I cried. And I’m not a sappy person.
What to see and do in Pienza
The Palazzo Piccolomini was the summer home of Pius II. The building is the perfect example of Renaissance architecture, with its stunning gardens, gorgeous courtyard and tall pillars. It is now a museum.
Pienza’s main cathedral, Cathedral of Santa Maria Assunta, has a traditional Renaissance-style façade and overlooks the main square. I like the more low-key churches of the smaller towns like Pienza, even though the churches themselves are all works of art.
If you want your picture-perfect setting of Tuscany, it can be found here, Belvedere, a street behind the Duomo in Pienza. The pedestrian path leads you along the wall of the town and crosses paths with Via dell’Amore (Love Street), Via del Bacio (Kiss Street) and Via della Fortuna (Good Luck street). It’s a romantic sight and gives you sweeping views of the Val d’Orcia.
While its neighbours Montalcino and Montepulciano are famous for their wines, Pienza is all about its cheese. Pecorino cheese is a creamy sheep’s cheese. It’s used in the best pasta dish in Italy – Cacio e Pepe. Pienza even has a festival devoted to its cheese, Fiera del Cacio, held on the first Sunday of September.
Where to find the best gelato in Pienza
Alright here’s the deal with gelato. It’s not just Italian ice cream. Gelato has less percentage of fat because made with more milk than cream. It’s churned slowly and with less air. In fact, if you see gelato that looks puffy, skip it and go to a shop that has “flat” gelato. It means that less air was used during the churning process, meaning better flavours.
Alright – controversy time – the best place to get gelato in Pienza, the best place to get gelato in Tuscany, no, the BEST PLACE TO GET GELATO IN ITALY is Buon Gusto Gelato in the heart of Pienza.
There I said it. Fight me if you need to because I stand by that statement.
The gelato here is the most flavourful, creamiest dessert made right there in the tiny shop. Go on, get some for yourself and convince me that it’s not the best.
Another tip to finding the best gelato is to find shops that ONLY sell gelato – that way you know you’re getting something that is made with love.
RELATED: Explore Venice from Rome in a day
Third stop: Montepulciano
Situated on a narrow crop of hills in the Val d’Orcia sits the hilltop town of Montepulciano. This is the largest of the three best Tuscan villages to visit and most known for its medieval history and its wine, the Vino Nobile.
Starting from the bottom of the hill, outside the city walls, you’ll realize you’re going to have to climb to get to the city centre. The people who live here must have perfect calves; everything is uphill. Yes – that physically doesn’t make any sense, but it just is.
The founding of the city dates back to the 4th to 3rd century BC, but it was really developed as a medieval town after the first millennium AD. The town is vibrant with old stone buildings, doors that look straight out of a movie and shops selling unique wares.
One draw to the city is the Bravio delle Botti, which happens mid-August every year. Teams of two representing eight districts of the town race along the winding uphill streets of Montepulciano to the town square. Oh, and did I mention that they are rolling 80kg wine barrels too? Not so easy.
You can watch the 2018 race here: (It’s in Italian)
What to see in Montepulciano
Porta delle Farine
One of the unique residences in Montepulciano is the Porta delle Farine. The apartment sits upon one of the Portos – or doors to the walled city centre. Called the Door of Flour, likely because this is where wheat and grain were weighed for tax purposes.
It’s now a B&B, and you can stay there!
Fortezza Di Montepulciano
Dating back to the 8th century, this fortress had undergone many changes over its lifetime. It’s now a cultural centre, where you can explore the exhibits and gardens overlooking the Val d’Orcia.
Here, in the centre of the city, you will find yourself surrounded by very imposing buildings, the central Duomo, the town hall, a museum and more. This is the highest point of the town and the most historic. On most days, it’s a relatively quiet space, but the town still holds important events here.
This is also where you’ll find the end of the Bravio delle Botti race. In the winter the town holds a Christmas market, just like the ones you see in northern Europe.
Did you know that Twilight: New Moon was shot here in Piazza Grande? Where are those sparkly vampires anyway? I didn’t see any.
The Cathedral of St. Maria Assunta
While the start of the construction of this cathedral started back in the 1500s, it’s technically not finished. The stone façade was likely to be covered in marble but never was. The bell tower beside it is much older, dating back to the medieval age.
This castle-like structure is actually the town hall for Montepulciano. Its white travertine façade reminds me of the elegant buildings in Florence, but it has a unique structure that catches the eye.
In the middle is the impressive clock tower where you can climb up to get a stunning 360-degree view of the city and surrounding landscape.
Piazza di San Francesco
While the town hall may get you a bird’s-eye view, the Piazza di San Francesco will get you the most beautiful. Overlooking the town and the Val d’Orcia, this small square, used mostly for parking, is a hidden gem. Take lots of pictures – you’re going to want to remember this view!
Church of San Biagio in Montepulciano
Just outside the city walls is the Church of San Biagio in Montepulciano. It’s a standalone building surrounded by a small park. The Church has an impressive structure, and of course, its history reads like a novel. The fresco of Enthroned Madonna and Child was reported to have healing powers, so it drew quite many people to it in its day.
Montepulciano’s Vino Nobile
Montepulciano really is the postcard-ready, picture-perfect Tuscan town. But it’s also known for the food and wine that are made here.
Like the Vino Nobile.
A Vino Nobile di Montepulciano is a fancy red wine made from a blend of Sangiovese and Canaiolo Nero grapes. The wine variety has been mentioned in text for centuries. It was given the “noble” name in the early 1900s.
Like its counterpart in Montalcino, the Vino Nobile was given the Denominazione di Origine Controllata e Garantita status.
It’s time to visit the best Tuscan villages
Visiting Tuscany can be easy when you know what you’re looking for. If you would to take a day trip from Rome, enjoy historical places and taste some of the best wines in Italy, then you have to visit the best Tuscan villages – Montalcino, Pienza and Montepulciano. You’ll never ask where to go in Tuscany ever again.
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