Are you travelling to Tuscany and wondering what are the best Tuscan towns to visit? Add the hilltop village of Pienza to your list. 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. Let this be your guide to touring this Tuscan Town.

How to Get to Pienza Tuscany

Pienza is a hilltop village that sits in the region of Val d’Orcia in the province of Siena. Although this area of southern Tuscany is known for its other principal towns of Siena, Poggibonsi, Montepulciano, San Gimignano and Chiusi – Pienza is truly a hidden gem. This Tuscan town is located right between Montepulciano and Montalcino, making it easy to see all three in one day.

Pienza is a hilltop Tuscan town located in the region of Val d’Orcia of the province of Siena. This romantic town offers visitors panoramic views of the beautiful countryside in Tuscany, Italy.

Here is a guide to driving distances from other popular destination points:

  • Montepulciano to Pienza is 20-minute drive
  • Siena to Pienza is a 60-minute drive
  • Florence to Pienza is a 90-minute drive
  • Rome to Pienza is just under 2 hours by car or 2.5 hours by train

History of Pienza

So, how did this Italian town come to be? Enea Silvio Piccolomini elected Pope Pius II in 1458, and 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 of Pienza.

Pienza is a hilltop Tuscan town located in the region of Val d’Orcia of the province of Siena. This romantic town offers visitors panoramic views of the beautiful countryside in Tuscany, Italy.

Pienza has remained virtually unchanged since the 15th century making it a top reason to come and visit this Tuscan town. 

Best Things to do in Pienza

Tour the historic centre of the city of Pienza

Let’s start with the historic centre of Piazza Pio II, the main hub of Pienza. Here 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

The Cathedral or Duomo was built on the remains of the Romanesque church of St. Mary which is still visible in the crypt. The façade is typical of the Renaissance and is divided into three parts by arched columns. 

Pienza is a hilltop Tuscan town located in the region of Val d’Orcia of the province of Siena. This romantic town offers visitors panoramic views of the beautiful countryside in Tuscany, Italy.

On the left wing of the Cathedral, there is an octagonal, cuspidate bell tower that is reminiscent of the ones Pope Pius II saw in Germany.

Pienza is a hilltop Tuscan town located in the region of Val d’Orcia of the province of Siena. This romantic town offers visitors panoramic views of the beautiful countryside in Tuscany, Italy.

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. Interestingly, Palazzo Piccolomini was the film location for Shakespeare’s “Romeo and Juliet” in 1968. 

Pienza is a hilltop Tuscan town located in the region of Val d’Orcia of the province of Siena. This romantic town offers visitors panoramic views of the beautiful countryside of Tuscany, Italy and many top things to do in Pienza

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.

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.

Pienza is a hilltop Tuscan town located in the region of Val d’Orcia of the province of Siena. This romantic town offers visitors panoramic views of the beautiful countryside of Tuscany, Italy and many top things to do in Pienza

Wander aimlessly through Pienza’s small alleys streets and shops

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

People watch in the piazza

Like any piazza in Italy, it’s where you will find locals gathering, 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.

Try some Pecorino di Pienza cheese

The main street in Pienza is Corso il Rossellino. This lovely street 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, it is always bustling with activity with locals stopping in to say ciao or picking up their daily products. During your visit to Pienza, you have to try the delicious Pecorino cheese they are so famous for. 

Gaze upon the panoramic views

One of the best parts of being in a hilltop town is of course the views. And, Pienza definitely has some of the best Tuscan countryside views. Find your way to Camminata Panoramica, along the path of the city wall. Gaze upon the hilly landscape of the Val d’Orcia behind the cathedral. This picturesque viewpoint should not be missed!

Go to Gladiator Point

Sitting below the city wall is the 11th century church of Pieve di Corsignano. This church is known as one of the most important Romanesque monuments of the region. From here take the 5-minute walk to De Cypresses or Gladiator point. This pathway is from the opening scene of the Gladiator movie and is incredibly beautiful.  

Where to Stay in 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 km), allowing you to see three small, yet lovely towns in one day. Maybe one for breakfast, one for lunch and one for dinner. Pienza is a destination for its restaurants. I recommend La Terrazza del Choistro or Osteria Sette di Vino.  

But if you would like to make Pienza your home base, this romantic town offers a wide range of accommodations, both in the old town and close to it. From agritourism to apartments to vineyard estates to wineries, agritourism, everything is represented here. Here are some of the best accommodations in Pienza.

  • Hotel in a 15th century convent: Relais II Chiostro di Pienza is located along the panoramic path on the city wall. This luxury hotel offers panoramic views, beautiful gardens, and a pool.
  • B&B in the old town: La Bellavita B&B delights with nice rooms and a very nice roof terrace with a fantastic view over the old town of Pienza.
  • Hotel in the historic center: Residence San Gregorio is a small, beautiful hotel at the gates of the historical center.
  • Agriturismo in a great location: Agriturismo Il Casalino is a 19th century farmhouse with individual apartments.
  • Agriturismo with swimming pool: Agriturismo Marinello is a beautiful farmhouse in a quiet setting overlooking Pienza. 
  • Or, explore other properties using Booking.com

Touring Other Tuscan Towns

While in this area of Tuscany, check out some of my featured guides for other beautiful destinations:

Experience | Discover Brunello wine in Montalcino with a ticket to the Brunello Temple, including optional wine tastings, click here to book in advance.

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, quiet towns and villages dotted along the Tuscan hills. Pienza just happens to be one of my favourites. I immediately fell in love with this romantic hilltop town with its incredible views and I know you will too. 

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104 Comments

  1. I loved the villages and architecture in Tuscany. I haven’t been to Pienza but it looks full of charm and reminds me a bit of Lucca and San Gimignano. Italy is so rich it needs a lifetime to see all it has to offer.

  2. The charm of Tuscany never disappoints. Incredibly, even though I’ve been to Italy many times, I have not explored much of Tuscany. Seeing these photos makes one want to wander through the alleys of these villages with such peculiar architecture.

  3. Very charming and romantic indeed. I wouldn’t want to squeeze in three towns in a day, I’d rather follow your advice and flanere around the small, narrow streets enjoy the hilltop views, and eat cheese. The restaurant scene in Pienza sounds ideal to me and I like that the place retains its charm. Let’s hope it won’t be discovered and overrun by tourists in the coming years.

  4. The Duomo is absolutely stunning. Simple in design, but gorgeous. The Italian countryside is beautiful so any place with a hilltop view is on my list! The Camminata Panoramica looks like a great place to stroll with gelato in hand 😉

  5. A road trip through Tuscany sounds amazing. This little town is so cute! I love the idea of a quieter and more intimate piazza, like you described here. Beautiful scenery!

  6. Montepulcian wine, as you say this town is near it, has been my favourite wine for years. I’ve always wanted to go there for this reason.
    A town with 3 places, all next to each – that was some work done in the past but how convenient for sightseeing! One even has a cinematographic reference and further along another gladiatiroial scene setting. Fame indeed.
    With names like Love Street and kiss Street this sounds one truly romantic location.
    Beautiful pictures and great info on local accomodation.,

    1. It really is the best place for foodies and wine lovers and to hop from one Tuscan town to the other. Pienza is a bit extra special as it offers some of the best views and it is incredibly romantic.

  7. What a gorgeous city! I showed your post to my friend who is obsessed with Italy. That city has so much to offer tourists, from history to architecture to nature. Those are the kind of places I love visiting. I feel at peace and mentally and spiritually recharged. I appreciate you adding so many photos. I am a visual person. I need to see pictures to appreciate text even more.

  8. This is the first I have heard of Pienza and am surprised it is well known for cheese. I don’t think of cheese when I think of Tuscany. The streets and views are enchanting for sure. Thanks for highlighting this off the beaten path gem

  9. Nothing is more attractive than quiet and intimate towns. The palazzo and cathedral are architectural masterpieces! A great reminder of the Medieval and Renaissance periods, like a place frozen in time.

  10. Oh how i’ve been dreaming of Italy! I went as kid and have always wanted to go back with husband. I’m less interested in places like Florence and Venice and sooooooo into towns like Pienza. You make it look and sound so dreamy. I could wander those cobblestone streets and hills for weeks!

  11. Pienza looks like the picturesque Italian town one could spent hours exploring. The churches and alleys are so charming. The countryside around must be wonderful too!

  12. Wasn’t Pienza just a little slice of magic?! Also, full of slices of cheese – I think I nearly turned into a wheel of Pecorino when I was there. A lovely revisit to a beautiful town, thank you so much!

  13. Reading this really makes me want to visit Italy. I have only been to Venice and Rome, but would love to do a roadtrip, or bike trip, across the entire country!

  14. A cheese shop!? A shop full of CHEESE!?? That’s so cutee I wish I could walk down the streets of Pienza and stumble upon little gems like that right now! Thanks for sharing 🙂

  15. You have put Pienza right on my wanderlist. I love the quiet yet interesting vibes about this place. I can definitely spend a few days just walking around and discovering the history around the place.. And those panoramic views – they are just stunning.

  16. There’s something about these photos that feel like they really capture the everyday magic and life that exists there, I adore it. I’ve never been to Italy but Tuscany is a dream destination for sure.

  17. 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

  18. 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!

  19. 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!

  20. 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.

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

  21. 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!

  22. 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.

  23. 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?

    1. 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.

  24. 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!

  25. 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.

    1. 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.

  26. 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

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

  27. 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

      1. Tuscany is definitely a place I’d love to visit one day and pienza sounds like a dream. I love the idea of the restaurants being tucked away in alleyways. So quaint and romantic. And I can NEVER bypass cheese! That alone makes me want to go.

  28. 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!

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

  29. 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.

  30. 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 (:

  31. 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.

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

  32. 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!

    1. 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.

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

  33. 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

  34. 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 . . . .

    1. Pienza, Tuscan town is couch a pleasant place to visit with the verdant vineyards and heritage homes. And all those variety of cheese is mouth watering 😋.

  35. 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!

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

  36. 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! 🙂

    1. 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.

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

  37. 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!

    1. 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.

      1. 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!

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

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

  38. 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

    1. 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.

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