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 Tuscan countryside in Italy.
Italy

Touring Tuscan Towns – Pienza

Are you traveling 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 of touring this Tuscan Town.

Where is Pienza located?

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

Here is a guide of 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

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.

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

Top Things to do in Pienza

TOUR THE HISTORIC CENTRE

Photo Credit: paolo alias opaxir

Let’s start with the historic centre of 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.

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.

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 of Tuscany, Italy and many top things to do in 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. Interesting fact, 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
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.

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 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.

STROLL THE STREETS

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
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 the delightful narrow cobbled stone streets in the historic centre. 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 Renaissance town. It features small but inviting piazzas with breathtaking countryside views, which are part of its charm. 

PEOPLE WATCH IN THE PIAZZA

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

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.

VISIT A CHEESE SHOP

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

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

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
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

One of the best parts of being a hilltop town are 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.  

Best Places 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 kms), 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 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

Pienza, a hilltop Tuscan town in Italy

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

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. 

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
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

Disclosure:  As an Affiliate Associate of Booking.com if you click on the link contained in this post, at no additional cost to you, I will earn a small commission if you decide to book. Thank you.

92 Comments

  • 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 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

  • Alice Mola

    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.

  • Ami Bhat

    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.

    • The.Holidaymaker

      Pienza doesn’t take long to wander, it’s that small. But it is a great village where the mood changes from morning to day to evening. Hopefully you get there one day.

  • Jill

    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 🙂

  • Bea

    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!

  • Cat @ Cat's Nine Lives

    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!

  • Natascha

    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!

  • Anne Howard

    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!

  • Trisha Velarmino

    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.

  • Sherianne

    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

  • Francia Henriquez Benson

    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.

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