One Day in Pienza (Tuscany) – The Best Things to See & Do

Pienza makes an excellent stop on any Southern Tuscany itinerary – but I know that it’s not always possible to spend a few days (or even one night).

If you’re anywhere nearby, it would be a mistake to miss out on Pienza. Where else can you find a post-card perfect hilltop town that’s a UNESCO World Heritage Site, is home to divine pecorino cheese and was created to be the Pope’s utopian city?

And did I mention you can recreate Russell Crowe scenes from the Gladiator or walk down streets named after love and kisses?

If that hasn’t sold you, you don’t deserve dear Pienza. But if you want to know more, let’s go!

Note: Since you’ve just got one day, I’m choosing my favorite way to spend a day in Pienza, based on my visits since 2003 as a guide, a traveler with my three children, and on dates with my husband to buy cheese (yes, it’s a thing). I can’t cover everything – just my top things to see and do in Pienza in a day.

Table of Contents

Pienza: A Hilltop Town in the Val d’Orcia

Pienza is in the southern part of Tuscany in the Val d’Orcia (Orcia Valley). It’s not far from other well-known Tuscan hill towns like Montepulciano and Montalcino, as well as lesser-known gems like Bagno Vignoni, Monticchiello, and San Quirico d’Orcia.

If you draw a line on a map between Florence and Rome, you’ll hit Pienza (although it’s closer to Florence).

Blue road signs point to signs for village in the Val d'Orcia in Italy. In the background is bright green grass and blue sky and rolling hills.

Driving Times and Distances to Pienza

Florence – 1 hr 30 min (115km)
Rome – 2 hr 20 min (190km)
Siena – 1 hr (55km)

When to Visit Pienza

Boy about to jump off stone steps onto brick ground. Large wooden door and stone building next to the step he's on. — We had Pienza to ourselves on this chilly winter day

Lovely any time of year but really quiet in the winter (besides around Christmas). Shops are shut but cheese places still open and some restaurants. We really love it in winter and early spring when it’s quiet.

Learn more about visiting Tuscany in the Spring – Summer – Fall – Winter

How to Spend One Day in Pienza

Park Just Outside Town

Arrive and park your car near the Coop grocery store.

Helpful Tip: Be extra careful not to park illegally here – I swear the vigili are hiding behind the bushes waiting for you to park in a spot you’re not supposed to.

Walk Through the Porta al Murello

Enter Pienza through the main porta (door), Porta al Murello. Walk into town through the arch and check out the main drag, Corso il Rossellino (named after the town’s architect, Bernardo Rossellino).

As you stroll, keep in mind that Pienza was built to be the Italian Renaissance ‘Ideal City.’ It was envisioned by Pope Pius II who was born in Corsignano (which was later named Pienza, after himself). You’ll notice the regal stone buildings here are quite different from the more casual ‘countryside’ buildings you see in neighboring towns like Montepulciano or Montalcino.

Fun Fact: Pope Pius II was previously called Enea Silvio Piccolomini – you’ll see his last name all over the area.

Stop in the Main Piazza

An empty Piazza Pio II in Pienza, Italy on a sunny day. Church ahead and palazzi on either side.

You’ll see Piazza Pio II (Pope Pius II Square) on your right. The main buildings are the Duomo (cathedral), Palazzo Comunale (town hall), Palazzo Vescovile / Palazzo Borgia (the Bishop’s Palace) and Palazzo Piccolomini (the Pope’s palace).

Fun Fact: Does the Palazzo Comunale look familiar? Its design was based on Florence’s Palazzo Vecchio.

Good To Know: If you have time, take the tour of Palazzo Piccolomini. You’ll see some of the Pope’s original furnishings and get an idea of how he lived. Plus, the views from the Palazzo’s garden are gorgeous.

Wander the Side Streets and Piazzas

Empty Piazza Spagna in Pienza, Italy. Orange and yellow buildings frame the small piazza. There is a stone well in the middle. Sign for Macelleria on building on left. — Piazza Spagna

I love the tiny Piazza di Spagna (just behind you when you’re facing Piazza Pio II) – it’s a nice spot for an outdoor meal or aperitivo. Explore the little side streets and make your way to the other end of town, Porta al Ciglio.

Just before the porta, turn right onto via del Casello.

Check out the Panoramic Pathway and the Love Streets

Sign for Via dell'Amore on a stone wall. On left is brick road with benches that leads to church bell tower. Above stone wall is large bush.

As you make your way down the pedestrian walkway of via del Casello, check out the fabulous views below of the UNESCO World Heritage Val d’Orcia. And, keep an eye out for small alleyways tucked in on the right:

Via del Bacio – ‘Way of the Kiss’
Via dell’Amore – ‘Way of Love’
Via della Fortuna – ‘Way of Fortune’

The path will lead you back to the main piazza. You can continue the path by walking around to the other side of the church. It finishes back at the main entrance, Porta al Murello.

Have Something to Eat!

Inside a small restaurant in Italy. Wine bottles hang by strings from the ceiling. Man looks at orders at the counter. Chalkboard menu in back. — Inside Baccano…

Child's hand reaches for salame on a wooden platter with cured meats and pecorino cheese. Bread basket in upper right. — Inside Baccano…

You can do this whenever you’re hungry! Some of our family’s favorite dining options in Pienza include:

Have a tagliere of local meats and of course, pecorino cheeses. We like the small Baccanoat via Rossellino, 9 (and you can also get panini made).
Have a leisurely meal at Il Rossellinoin the charming Piazza Spagna. It used to be run by an older local couple, and the management has changed hands (I’ve been visiting since the early 2000s so I was nervous to see a big change) but still makes delicious local pastas like pici. You can sit indoors or on the piazza.
Gather supplies for a small meal or aperitivo with a view of the Orcia Valley. I like this spot with a couple of benches and a chest-level stone wall that’s wide enough to spread snacks out on. You’ll find an excellent selection of pecorino di Pienza at shops in town. My favorites are Marusco e Mariaon via Rossellino (excellent selection plus tons of food treats and souvenirs) and Ernello’s shop just outside the town walls (via Mangiavacchi, 42). You can also shop at the little Coop by the parking lot.
Classic restaurants include Sette di Vino, La Buca di Enea, and Ristorante dal Falco (often overlooked because it’s outside the town center, but it’s consistently delicious).
In the mood for carne (meat)? Try Pio Burger in town or BBQ Chianina Station just outside (on the other side of the main road, SP18).
Don’t forget gelato! Three words -> Buon Gusto Gelateria.

Walk Down to the Pieve di Corsignano

View of grassy area with cypress trees and a stone church with a round bell tower.

Close up of stone church facade with sirens. and monster-like creatures.

The Pieve di Corsignano (aka Pieve di Santi Vito e Modesto a Corsignano) is a Romanesque church below town that was the site of Pope Pio II’s baptism. Even though I don’t really consider myself a ‘church person’ (I prefer to see other monuments and sites), I try to walk down here whenever we’re in Pienza.

It’s in a quiet spot and it’s an interesting small church – even if it’s locked, you can check out the (possibly) pagan symbols on the façade (sirens, Mother Earth) and the unique round bell tower.

You walk a little further and see where Russell Crowe filmed scenes from the Gladiator. To reach it – with your back to the Pieve di Corsignano, walk forward to the gravel road directly in front of you. You’ll turn LEFT toward the sign for ‘Agriturismo TERRAPILLE.’ Depending on the time of year, there may not be wheat growing, but you’ll still get fantastic views. And, if you like the walk, you can keep going and then turn back around whenever you like.

Good To Know: You’ll be walking downhill (so make sure your shoes have good tread) and on some dirt/gravel if you decide to walk to the Gladiator set (so make sure you’re not wearing fancy shoes that can’t get a little dusty or muddy, depending on the road’s condition).

Go Pecorino Shopping

This is the place to pick up pecorino cheese to take home with you or use for picnics on the rest of your trip. I even come here on dates with my husband – to buy cheese. I mentioned my two favorite shops above – Marusco e Maria on the main drag and Ernello’s Shop (Il Cacio di Ernello) just outside the town walls.

At this point, you’ll either head back to your car and toward your accommodation for dinner closer to ‘home’ or have aperitivo and dinner in Pienza.

Helpful Tip: Don’t rush through Pienza. It’s tiny, so you could ‘see’ Pienza in five minutes, but the beauty of the village lies in the moments – stopping in at the little cheese shops, listening to the nonne chat in their apartments, lingering on the town walls to watch sunset over the Val d’Orcia.

Things to Do Near Pienza

Group of cypress trees in an empty field. It's nearing sunset time. Grass is bright green and there is a ring of dirt around the base of the trees. — The San Quirico cypress trees

Looking to add to your Southern Tuscany itinerary? There are so many things to see and do within an hour’s drive, including:

Podere il Casale – visit the farm and try the cheese, or join a cooking class
Cypress Trees of San Quirico – stop by some of the Val d’Orcia’s famous trees (you can find them here)
Bagni San Filippo – hot springs!
Montalcino – home to Brunello wine, compact and charming village center
Sant’Antimo Abbey – incredible abbey just south of Montalcino
Bagno Vignoni – small thermal bath village with small hot springs just below town; the main piazza is a thermal bath (but no swimming allowed)
Cortona – yes, the one from Under the Tuscan Sun; lively, artsy hill town
Buonconvento – tiny center with excellent restaurants; close to the incredible Monte Oliveto Maggiore Abbey (jaw-dropping frescos and you can buy honey from the monks to eat with your pecorino cheese)
Siena – home to the Palio horse race; it’s Piazza del Campo is one of Italy’s loveliest piazzas
Perugia – university town; home of Perugina chocolate factory (you can take a baci-making class at the factory in San Sisto
Deruta – some of Italy’s loveliest ceramics

If you’re willing to travel further (1.5 to 2 hours), you could also reach:

Boy pointing to colorful sculptures at the Tarot Garden in Tuscany, Italy. — The Giardino dei Tarocchi

Saturnia – Tuscany’s most famous hot springs
Capalbio – on my list of the most beautiful small villages in Italy; near the Giardino dei Tarocchi
Pitigliano – a tufa town with a dramatic hilltop setting
Monte Argentario – charming port towns, lovely beaches
Maremma beaches – some of Tuscany’s best – both wild and with beach clubs
Monteriggioni – a tiny, medieval, walled hilltop town

I hope you enjoy your day in the ideal Renaissance town of Pope Pius II and the home of pecorino di Pienza!