Tuscany’s Hill Towns – A Two-Day Itinerary

Tuscany’s Hill Towns – A Two-Day Itinerary

Tuscany was one of the highlights of our trip to Italy. Well, to be honest, it’s hard for something in Italy not to be a highlight, right? Here we share with you an itinerary you can follow to visit some of Tuscany’s most amazing destinations. In the first half of our 4-day itinerary, we’ll cover some charming hill towns where you can indulge all your senses with amazing views, world renowned wines and cheeses, and much more: Let’s get started: 



Montepulciano is one of the biggest hill towns in central Tuscany. It’s surrounded by vineyards where the sangiovese grape is grown – the raw material for making the town’s famous wine: vino nobile di Montepulciano.

Montepulciano seen from the road.

How to get here 

As we mentioned on our post about roadtripping in Tuscany, the easiest way to arrive at Montepulciano, if you are coming from the south (Rome) or from the north (Florence/Venice/Milan) is to first get by train to the town of Chiusi. There, you must rent a car, and Montepulciano is some 40 minutes away. For more details regarding renting the car and driving around Tuscany, check out that blog post, here’s the link: Renting a Car & Driving in Tuscany

What to See and Do

Walk up the steep streets up to the main square 

We have to say this from the start: the streets that lead up to Montepulciano’s main square can be quite steep! But don’t worry, they are so nice and there’s so many thigs to stop for along the way that you won’t feel the effort!

Montepulciano street

Wine bars, gelato shops, artisan’s workshops and terraces with great views will surely make you stop on your way up!

Look out for terraces on the sides of the town for the views

Since it’s located on the top of a hill, you can imagine that there will be some spots on the edges of the town with some sick views of the surrounding countryside.

Keep an eye open for them!

Go into every little church

On your way up you will find various little churches along the way that may not seem like much from the outside, but are so charming inside, so always take a peek inside! It’s free!

Once you get to the main square, you can’t miss the town’s main church located there either!

Visit the Wine Cathedral + wine tasting at Palazzo Ricci

Yes, you read correctly, WINE CATHEDRAL! About one block away from the main square you’ll find the Palazzo Ricci: a palace that was home to one of the town’s wealthiest families. The terrace on the upper level has some of the best views to the surrounding fields, but the real treat begins when you step inside and climb down the stairs.

Deep inside the palace there some huge cellars where wine is still aged in huge oak barrels! It’s know as the Wine Cathedral, and with good reason!

There’s also an ancient Etruscan cave where wine has been aged for more than 2,500 years!. At the end of the tour, on the lowest level of the palace, you’ll find the cantina where you can taste some of their wines for 5 euros. If you buy a bottle, as we did, the tasting is free.

This was definitely one of our favorite things to do in Montepulciano. There are lots and lots of wine cantinas and cellars in the town, but we don’t think that any of them would top the Wine Cathedral! 

Agriturismo – Dinner with a view

A trip to Tuscany will never be complete without staying at a rustic agriturismo. This is, in our opinion, the perfect way to discover the region’s rural way of life and enjoy the Tuscan dolce vita! Great food, great wine, great views, wineyards and olive groves, welcoming Italian hosts…what else could you ask for? We stayed at Agriturismo Il Burellino, located less than one kilometer away from the gates of Montalcino. We headed there immediately after leaving Montepulciano. If you want to read and see more about this agriturismo, check out our blog post: 6 Reasons why you need to stay at Agriturismo Il Burellino.

Whether you stay at Il Burellino or any other of the many available agriturismos around, it’s definitely a recommended thing to do. In our case, we arrived at the agriturismo as the afternoon was fading away, so we ordered a cheese and meat platter with some of the best local delicacies, and a bottle of wine, and simply sat in the little terrace just outside our room and enjoyed the incredible views of the wineyards and hills below as the sun went down.

After this, we had our main course of pasta with a couple of glasses of the world famous Brunello di Montalcino wine.


Wineyard Tour

The second day of the itinerary begins in the agriturismo. Il Burellino, as most (if not all) agriturismos, has its own wineyard. Here they grow fully organic sangiovese grapes, the ones used in the region’s most renowned wines.

There’s hardly ay better way of spending a morning in Tuscany than strolling through a wineyard learning all about the grapes and the wine making process. 


After the wineyard tour and getting a shower and fresh clothes, we set course at midday to Montalcino.

Montalcino seen from the road.
Montalcino seen from the road.

How to get here 

As we said before, in this region of Tuscany the best way to move around is by car. If you stay at Agriturismo Il Burellino, Montalcino is just 5 minutes away, so getting there is a no-brainer. Anyway, it’s just over an hour from Montepulciano, and half an hour from Pienza.

What to see and do

Lunch with views at Alle Logge di Piazza

The first thing we did after parking our car was looking for a restaurant to have lunch. At Agriturismo Il Burellino we got a recommendation that proved to be great: Alle Logge di Piazza, a restaurant located on the main square.

You can sit in the tables in the square itself, or even better, step inside and sit in the table that is just by the window, for amazing views to the Tuscan countryside as you enjoy some delicious pasta and wine.

Wander around its sleepy streets and squares

Montalcino is much smaller and not so steep as Montepulciano, so walking around the town won’t take much more than a couple of hours.

As in Montepulciano, you’ll find souvenir shops, gelaterias and wine bars where you can try the famous local wine: the brunello di Montalcino, nicknamed “the king of wines”.

Go up the Fortezza for breathtaking 360° views

Probably Montalcino’s greatest attraction, the Fortezza or fortress is located in the highest part of town. For 4 euros you can get up on the walls, where you will get amazing 360º views of the world famous Tuscan countryside. It’s such a beautiful combination: the red earthy colors of the houses and rooftops, the green fields and blue sky.

Inside the fortress itself there’s a wine bar where you can enjoy a wine tasting, if you wish. 


After leaving Montalcino, as the sun was beginning to come down and we got into the beautiful golden hours, we headed to an even smaller, but no less charming town: Pienza.

How to get here 

Pienza is located halfway between Montepulciano and Montalcino, no more than 30 minutes away by car from each of these towns.

What to see and do

Get lost in fairy tale-ish alleys

As you walk into Pienza’s old town, you’ll get the feeling of being inside a fairy tale: rustic houses decorated with hanging flower pots and stone streets.

The old town is quite tiny, it doesn’t take more than one hour to walk all around it, but it’s a treat for the eyes to wander these lovely alleys. Just look at these:

Enter the main church and see the views behind it

In Pienza’s main square you’ll find this beautiful church. Be sure to step inside to see its delightful interior.

Once you step outside, walk towards the rear side of the church and we promise the views will make you drop your jaw! We’ll let this image speak for itself:

Pecorino cheese tasting + try pecorino gelato

Pienza is not famous for its wine, like its neighbors Montepulciano and Montalcino, but for the production of pecorino cheese. Btw, did you know that the name “pecorino” comes from the Italian word “pecora”, that means “sheep”? There are lots of cheese shops around Pienza, and you can smell the delicious scent in most parts of the town.  Step inside one of the many shops and enjoy different kinds of pecorino cheeses: aged, infused with pear or with bits of black truffle are amongst the many you can try.

One thing that actually surprised was winding a gelateria that sold pecorino gelato! We had to try it! The shop owner suggested we try it paired with pistachio, and what a great recommendation that was! If you have tried pecorino, don’t imagine the gelato with its strong, salty flavor, but instead try to imagine a cheesecake flavor with an unmistakable scent of pecorino. It was truly delicious!

Pienza is definitely one place where we wished to have stayed for a longer time. Even though it’s so small, there are so many other thigs to do, like visiting a farm or signing up for cheese making lessons!

There are many other things to do in these towns, and plenty of other charming towns to see in this area of Tuscany, but unfortunately we only had a couple of days to see them! We would totally love to stay here for at least one week and explore this gorgeous region in greater detail!

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