Visit Pienza, a lovely hilltop town in Tuscany

Touring Tuscan Towns – Pienza

Are you traveling to Tuscany and wondering what are the best towns to visit? Well, add Pienza to your list. Pienza, a hilltop village, sits in the Val d’Orcia part of southern Tuscany in the Siena region. This UNESCO World Heritage site is famous for its Pecorino di Pienza, a hard sheep’s milk cheese. You will find it prominently displayed in some of the specialty cheese shops in this region. But it is more than just that. Come, let me show you…

Touring Tuscan Towns - Pienza |

I immediately fell in love with this small, quiet, romantic town. Wander the delightful narrow cobbled stone streets, with names of Via dell’Amore (or Love Street) and Via del Bacio (or Kiss Street) and you can’t not help but fall in love with this town. It features small but inviting piazzas with breathtaking countryside views, which are part of its charm. 

Touring Tuscan Towns - Pienza |

Pienza's origins...

So, how did this town come to be? Enea Silvio Piccolomini decided to elect Pope Pius II in 1458. It was he who wanted to transform his birthplace, the anonymous village of Corsignano, into the ideal Renaissance town. He hired Bernardo Rossellino, and it only took 4 short years to rebuild and rename the town to Pienza. It has remained virtually unchanged ever since.  

Touring Tuscan Towns - Pienza |

Around the town...

Let’s start with Piazza Pio II, the main hub of Pienza. Here is you will find all of the town’s main monuments. It is flanked by the cathedral and three palaces: one for the government, one for the bishop and one for Pope Pius II.

Photo Credit: paolo alias opaxir
Visit Pienza, a lovely hilltop town in Tuscany

The Cathedral was built on the remains of the Romanesque church of St. Mary (still visible in the crypt). The façade is typical of the Renaissance and is divided into three parts by arched columns. On the left wing there is an octagonal, cuspidate bell tower that is reminiscent of the ones Pope Pius II saw in Germany.

Touring Tuscan Towns - Pienza |

Next is Palazzo Piccolomini. This was Rossellino’s masterpiece and has a three-arched loggia on the ground floor facing the cathedral with the council chamber above it. 

And then there is Palazzo Borgia (Palazzo Vescovile) which was given by Pius II to Cardinal Rodrigo Borgia (the future Pope Alexander VI). This is home to the Diocesan museum. The collection includes local textile work as well as religious artifacts.

Touring Tuscan Towns - Pienza |
Touring Tuscan Towns - Pienza |

And the last building is Palazzo Comunale, the town hall. The contrasting red brick bell tower was added afterwards. It was purposely built shorter than the cathedral’s bell tower to symbolize the superior power of the church.

While in Pienza...

Like any piazza in Italy, it’s where you will find locals gather, catching up on the latest news (or maybe it’s the town’s gossip) and children playing football (soccer). What is missing is the opportunity to dine al fresco, for that, you will find dining tables and chairs tucked away on tiny side streets. This is what makes Pienza’s piazza a bit different. I for one, rather liked it. It seemed quieter and more intimate. The only real noise you heard was the echoing sounds of the pigeons fluttering about and cooing.

Pienza, a hilltop Tuscan Town featuring the best views, unchanged Renaissance architecture and dining options.

Pienza’s main street, the lovely Corso Rossellino, is lined with little shops. There are an abundant amount of food shops showcasing typical Tuscan products, and yes, cheese. For such a small town, they are bustling with activity with locals stopping in to say hi or picking up their daily products. 

There are many cheese shops, but my favourite was Marusco e Maria Enoteca

One of the best part of being a hilltop town, are of course, the views. And, Pienza definitely has some of the best Tuscan countryside views.

Curiously, as you wander down an alleyway and start to see  glimpses of the pale blue sky and green rolling hills, just like this one…

Touring Tuscan Towns - Pienza |

And, then this is your view…

Touring Tuscan Towns - Pienza |

If you are touring Tuscan towns, Pienza makes a lovely day trip. If rushed, you could combine it with Montepulciano (15kms) and Montalcino (20 kms), allowing you to see three small, yet lovely towns in one day. Maybe one for breakfast, one for lunch and one for dinner.

Speaking of food, Pienza is a destination for its restaurants too. I recommend La Terrazza del Choistro or Osteria Sette di Vino. If you want to make this town your home base, why not stay at some Airbnbs. I recommend Villa il Tiglio or Il Rocchetto.

As a holidaymaker…

Tuscany is definitely one of those destinations that you are sad to leave and you long to return to. There are just so many small towns and villages dotted along the Tuscan hills. Pienza just happens to be one of my favourites. 

Pienza, Italy. This beautiful hilltop Tuscan town needs to go on your list.
Pienza, Italy. This beautiful hilltop Tuscan town needs to go on your list.

Disclosure:  if you click on the Airbnb links contained in this post, at no additional cost to you, I will earn a small commission if you decide to book. 


  • Anisa

    I would love to visit some of the smaller towns in Tuscany and Pienza looks lovely. I would love to taste the cheese and visit the Cathedral

    • The.Holidaymaker

      There are so many lovely towns in Tuscany, hopefully this helps to narrow down the list! The cheese was delicious, and all so very different tasting, dependent upon the aging process. Thanks for commenting.

  • Angela

    What a dreamy little village to visit, it looks like you had it to yourself. I like the idea of doing the 3 centres in a day for breakfast, lunch and dinner!

    • The.Holidaymaker

      I know a lot of people like to squeeze as many places into one day as possible, so it is definitely doable, and something we did to maximize our day. I especially loved Pienza and could have stayed longer. There were far too many fantastic places to dine.

      • Desiree C

        That is the most adorable Italian town!

        I’ve been to Cinque Terre, but I feel like I missed out on something very quaint by not visiting Pienza.

        Great post!

        • The.Holidaymaker

          Thank you Desiree for your comment. Yes, the quaint village of Pienza is pretty special, but so is Cinque Terre.

      • The.Holidaymaker

        Thank you Brooklyn for commenting, and hopefully one day you’ll be able to experience it yourself.

  • Cristina

    I cannot wait to visit Tuscany, it looks such a beautiful place! I love your tips and recommendations and I am definitely saving these 🙂

    • The.Holidaymaker

      Thanks so much for your comment Cristina, I am so glad you found these helpful for when you hopefully get to visit there.

  • Jan

    Tuscany is one of my favorite regions in Italy. We visited this place ages ago but I still remember the narrow cobblestone streets, arches and gentle rolling hills. Your pictures are really beautiful!! I will mark Pienza for my next visit. Thanks for sharing this beautiful blog! 🙂

    • The.Holidaymaker

      Thank you Jan for your comment and such kind remarks. Indeed Tuscany is a special place to visit. I hope to return one day again one day soon.

  • Jamie Italiane

    Although I have traveled around Italy, I have never been to Tuscany and you have definitely inspired me to visit not only this gorgeous town in the hills but the whole region. Those buildings!

    • The.Holidaymaker

      Thank you for stopping by Jamie, and I am so glad I inspired you to check out this beautiful region.

    • The.Holidaymaker

      Thank you Amit, stay tuned there are a lot of places in Italy that I need to write about. 😊

  • Ada

    Looks amazing! Reminds me a lot of Assisi, which was probably my favorite place I visited in Italy. Thanks for a great tour of the town. Now I want some Pecorino . . . .

    • The.Holidaymaker

      I didn’t make it to Assisi, and would love to return to see more. Thanks for your comment Ada!

    • The.Holidaymaker

      I know, it offers all the essentials – I don’t think you need anything more than that!

  • Josy A

    Oh Renee, you do always seem to find the most beautiful small towns to explore. The whole of Tuscany looks beautiful, but Pienza seems perfect. I can totally see why it charmed you so much (especially with those loved-up street names – you might have to go back for valentines day!)

    p.s. those views! <3 <3

    • The.Holidaymaker

      Thank you Josy! That was my feeling exactly – this is a perfect destination for Valentines Day!

    • The.Holidaymaker

      Thank you for your comment. I am so glad you agree that it offers the perfect Tuscan experience.

    • The.Holidaymaker

      Thank you fellow Canadians for your comment! I hope you enjoy your tour to Italy! It is a beautiful country to visit.

  • Desiree C

    Wow! Pienza is such a cute Northern Italian village. I’ve been to Cinque Terre, but I feel like visiting these villages that are less touristy would be such a great experience. Plus that cheese sounds delicious!

    What a great post!

    • The.Holidaymaker

      Thank you Desiree for your comment. Actually the Tuscany region is in central Italy, just an hour or two north of Rome. Not as far as Cinque Terre. I loved visiting the non-touristy areas of Italy.

    • The.Holidaymaker

      It definitely is that Catherine. Thanks for your comment and hope you get to visit it one day!

  • Rudy @ Backpack & Snorkel

    We have been in Italy and toured the big cities, but haven’t made it to Tuscany yet. I have seen those gorgeous old towns on TV and now in your blog. Yes, this is definitely something we need to do when we get back to Europe.

    • The.Holidaymaker

      Oh most definitely Rudy! The Italian countryside is pretty spectacular! Hope you make it back one day!

  • Raquel

    I love your descriptions of these towns! It seems like they’re the kind of places where you could easily strike up a conversation with the locals (:

  • April

    I read a lot about Tuscany and it seems a great place to visit and relax when you are in Italy. To get away the crowded city for a bit. I hope we can visit there someday.

    • The.Holidaymaker

      It most definitely is April. It is relaxing, laid back and oh so beautiful. Thanks for stopping by.

  • Jackie Gately

    I adore these little Tuscan towns, too! I have never been to Pienza, though. It looks lovely from your photos. I can’t wait to go back to Tuscany–and I’ve added Pienza to my list of must-see hilltowns. Your suggestion to combine it with Multepulciano is a great idea, too!

    • The.Holidaymaker

      Thanks Jackie for your comment and so happy to hear you will add it to your itinerary. I am sure you will love it!

  • Lydia

    I absolutely adore Italy and this place seems to beautiful and rich in history, I will definitely make a stop there on my tour around the country

  • Jeremy

    I see you love visiting small villages, and especially taking photos of the back alleys ! I love them too ! Did you get to eat any good pizza ? =p

    • The.Holidaymaker

      Thanks Jeremy for your comment! Lots of great pizza, just not in this town. It was all about the cheese and wine for me.

  • Anshul

    This place looks like it popped out of Game of Thrones. Since I have a special affect towards medieval towns, I would love spending my time here.

    • The.Holidaymaker

      Thank you Anshul for your comment. Yes this is one medieval town that has not changed since it was first built all those centuries ago. Glad you like it.

  • Dani

    Such a romantic little town! I absolutely love Tuscany (I mean, who doesn’t), because of storybook little towns like this. I love that the piazza is not full of al fresco dining – different from most places in Italy, but I bet the quiet is nice!

  • Kevin | Caffeinated Excursions

    Pienza looks so lovely with such a rich and long history. I think I’m most intrigued by how cohesive all the architecture seems to be. I wonder if that’s just because everything has had the chance to age or because it was all designed by Bernardo Rossellino. Maybe a bit of both?

    • The.Holidaymaker

      Kevin you are so right, I think it might be a bit of both. It has been so well preserved and unchanged since the original redesign of it by Rossellino. Thanks for your comment.

  • Alice Ford

    What a charming town. I would certainly combine it with Montepulciano as that’s one of my favorite wines. Nothing better than some great cheese and some great wine, while touring the Italian countryside.

  • Jas

    Ooo you had me at cheese! Love wandering through local streets and little shops. Plus, I can never say no to stunning views. I’ve honestly been dying to visit Tuscany and Pienza looks like such a beautiful spot that I definitely need to add to my bucket list. Can totally see why you’d fall in love immediately!

    • The.Holidaymaker

      Ooo I am so glad you liked it Jas and that it inspired you to add it to your future travel list!

  • Federica

    The balcony over the sweet hills of Tuscany is still one of my best memories about Pienza along with the beautiful square with the chi=urch. I hope that from there you had time to visit the enchanting village of San Gimignano and to clomb on one of his numerous towers.

    • The.Holidaymaker

      Thank you Federico for your comment. You are so right the views along the back side of Pienza are simply incredible.

  • Riana Ang-Canning

    Oh I am craving a trip to Italy so badly right now! This instantly brought me back to our time in Tuscany last September. We didn’t make it to Pienza but I felt similar vibes with the views, architecture and shops in San Gimignano. Adding this one to my list for my next Tuscany visit!

    • The.Holidaymaker

      Definitely do Riana, it was one of my favourites. Such a great town for foodies too.

  • Gus Feliciano

    This looks amazing, I am a sucker for small country towns and then you added cheese so I am in heaven!

    Italy always looked like a fun place to visit but I am so more intrigued now on small town Italy rather than big city Milan, Rome, etc.

    Looks great!

    • The.Holidaymaker

      Thank you Gus! My recommendation is to do a bit of both – big cities and small towns.

  • Emma

    What a gorgeous little town, I’m in love with the small streets and the history of the town and definitely want to add this to my list. Plus an entire town that revolves around cheese is my kinda place

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