Quintessential Tuscan countryside
Europe,  Italy,  Travel Bag

A whirlwind tour of Tuscany – Montepulciano, Pienza and Montalcino

Tuscany ! The mere mention of the name conjures up images of gently rolling hills, acres upon acres of vineyards, with tiny beige and yellow settlements clinging to the top of the hills. So it is no surprise at all that out of one of our days spent visiting Florence, we make a day trip to the countryside to visit the Tuscan hill towns of Montepulciano, Pienza and Montalcino.

How to get to the Tuscan countryside

The Tuscan countryside can be a little difficult to get to as there are no major train stations in the region. So the easiest, and the laziest option is to book one of the numerous operators that offer guided day trips to various towns and villages in Tuscany. The options are most often limited to a packed itinerary that involves Siena-San Gimignano-Chianti and sometimes even Pisa. Seasoned travelers usually frown upon such an arrangement but these day trips have a thriving market.

Travelers who have the luxury of time, catch a bus or drive a rented car down to one of the villages and stay there for a couple of days, experiencing the true sun-soaked Tuscan way of life. Bus options, in Italian, can be checked here and here.

We on the other hand, have also opted for a day trip. This one involves a tour of the picturesque Val D’Orcia in Tuscany, which is the sight that you see online most often. Fortunately for us, this is a region that most tourists opting for the Siena leg will never come close to, which is virtually a guarantee of lesser crowds.

Onward to Montepulciano

We have had an early start to the day and Francesco, our B&B host has just bid us “Ciao” after a hearty breakfast. A van picks us up and escorts us to a meeting point near the railway station where tourists on the same itinerary are marked with colored pin-it stickers. Ours is a deep green, but we are not jealous of the packed buses that are departing for Siena and Cinque Terre.

An hour later, our bus heads south of Florence, crossing uncrowded roads, with the Duomo’s red bricked cupola bidding us “buon giorno” for the day. It drizzles and we sleep, hoping for some sunshine up ahead.

Silvia, our Spanish tour guide jolts us out of our reverie when she announces in English that we are nearing Montepulciano and might as well accompany her for a tour of the wine cellar that makes the famous Montepulciano wine. As we gape outside, miles of vineyards laden with big round grapes greet us, the famous and eponymous Montepulciano variety.

Once the claustrophobic wine tour is finished, we strike off on our own to explore the little town.

All of these Tuscan towns are situated on hills, meaning, Montepulciano will have steep upward sloping roads and alleyways.
..with pricey souvenirs in the form of painted ceramic plates and artwork of the Tuscan countryside. But these do look authentic in contrast to the ones we have seen in Florence’s Mercato Centrale.
Santa Maria della Grazia at Montepulciano
Up the top of the hill is a piazza, the Piazza Grande with a medieval looking church and a palace that resembles the Palazzo Vecchio in Florence.
View from Montepulciano
View from the top of Montepulciano


Next on the whirlwind tour, announces Silvia, is the charming little town of Pienza. As the bus speeds towards Pienza, she tells us that the settlement is usually referred to as the ‘ideal city’ here in Tuscany. But it is so small that you can finish sight-seeing within half an hour. Pienza is also famous for it’s pecorino cheese, a hard, salty variety that is made from sheep’s milk.

Personally for us, we are agog with excitement. Pienza also lays claim to courtyards that offer sweeping views of the famous Tuscan landscape. Famous movies like The English Patient, Romeo & Juliet as well as Gladiator were filmed here. And true to it’s fame, Pienza does not disappoint.

Rolling hills of Tuscany in Pienza
Rolling hills of Tuscany in Pienza


Rolling hills of Tuscany in Pienza
Cypress tree lined sinewy roads dot the picturesque landscape of Tuscany

Thankfully, the foreboding clouds have receded and we are blessed to see sunlight baking the Val D’Orcia from balconies in Pienza. The brick and stone structures in Pienza are a mishmash of red, yellow and orange and they seem to bask proudly in the day.

Pienza's alleys - romantic and full of Tuscan character
One of the alleys in Pienza, bursting with typical Tuscan character and so quaint and charming.
The main street in Pienza
We could walk from end of Pienza to the other in about 15-20 minutes. The dreamy ambience of the town makes you feel like it is a lot lesser than that. Along with movies, even a video game called ‘Assassin’s Creed’ had Pienza as a setting.

Soon, it is time to depart Pienza and we move on to our next destination for the trip, the biggest town we’re to see during our day – Montalcino. On the way, our bus passes through the Val D’Orcia.

The scenes are stunning though. The landscape has countless gently sloping hills that have been ploughed through, and are all muddy brown in the shadows, but gleam golden when the sun breaks through. If we were not fully awake, this dreamy landscape would have felt alien, as if Tuscany hid another planet within itself. Bales of hay and patches of shrubs and cypress trees break the monotony of yellow and brown. It is no surprise therefore that UNESCO has chosen this valley as a proud member of it’s world heritage sites.

The landscape is not totally isolated though. In between, we catch big, solitary houses, their entrances guarded by cypress trees planted in perfect alignment with the curvature of the roads.

Quintessential Tuscan countryside
These Italian cypress trees added so much symmetry and beauty to the otherwise austere landscape in summer. One wonders how glorious the landscape would appear in spring.


Montalcino feels surprisingly large after Pienza. We are a little famished as well and hunt around for a pizza. A pizzeria in the town square, the piazza del popolo is just closing down and we ask the lady for a slice of delicious pizza with a bottle of coke and it amounts to just 4 euros ! That is the cheapest lunch we’ll ever have in all of Europe, and it makes for some very happy tummies.

Montalcino is famous for another of Tuscany’s wines, the Brunello di Montalcino. We also sight shops selling exquisite Fedora hats made of felt and leather, along with leather handbags and purses that seem far better in quality to the ones we’ve seen so far in Florence.

The fortress at Montalcino
Montalcino boasts of a 13th century fortress that to my eyes, somehow embodies the term ‘medieval’. The view that you get from it’s ramparts is phenomenal. And if you get tired of climbing and walking, there is even a cafe within it’s walls.

As the church bell rings, it signals the end of our trip to the countryside and we stroll back leisurely through the streets toward our bus. The sun is almost saying goodbye and it manages to color the Tuscan skies a tinge of purple and rich orange, visible through the windows of our bus as we speed back north towards Florence.

This landscape, as I am sure history also agrees, is itself a work of art that doesn’t need museums or closed doors. And today, it continues to astound us as travelers, as it once inspired Renaissance era artists. “Que bella“, as they say here in Tuscany.

Tips on visiting Montepulciano, Pienza and Montalcino.

As always, it is recommended that one plan for Tuscany and let the experience seep in gradually instead of a rushed day trip to the countryside. Siena and it’s adjacent towns of San Gimignano are crowded and the Val D’Orcia route is usually a little less popular. 

It is also a pretty straightforward bet to hire your own car or bike (of a vintage make hopefully), to make for a slow (read leisurely) drive into the hills of Tuscany.

Montalcino is the biggest of the 3 towns however stay options, with some really fantastic agriturismos, can be found in all the 3 towns.

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