Pienza: Tours, Tips and Awesome Things To See and Do

Pienza is the ultimate getaway city for those looking to spend time from the urban hustle of modern life. Pienza is a quiet town, set against an idyllic Tuscan countryside, and with an atmosphere, architecture, history, and vibe to match.

Pienza is a lovely small town in Val d’Orcia, famous for being a great producer of a special type of cheese made from sheep’s milk: Pecorino di Pienza! Val d’Orcia is a beautiful valley in the heart of Tuscany with some of the most beautiful hilltop villages in Italy, like Montepulciano, Montalcino, Bagno San Filippo e.t.c.

Pienza’s carrugio/streets are narrow and homey; balconies and terraces hanging over the streets simply invite you for a stay in this quiet commune that is a home away from home. An evening walk here is like an endless night’s venture amongst town made for lovers. With the green of the countryside, the floral pots and flowers set against every doorway and window and balcony, Pienza was just the thing I needed after a week of rushing here and there in preparation for the new year.

My hope today is to offer you a glimpse of Pienza. Her history and culture, the things tourists see and do, the little secrets hosts keep to themselves, and my own take on Pienza.

How to Get to Pienza from:

1. Rome to Pienza:

2. Florence to Pienza:

3. Siena to Pienza:

4. Milan to Pienza:

A Utopian History of Pienza

Pienza’s history is tied to the village of Corsignano, surrounding the 8^th century AD Castello di Corsignano. Till then, it was little known save for the fact that it was a Tuscan village, replete with all the beauty that Val d’Orcia has to offer.

Then her fortunes turned in 1458.

Eneo Silvio de Piccolomini, aka Aeneas Silvius Piccolomini, became Pope Pius II. Born from the region and influenced by the progressiveness and beauty of the Renaissance, Pius II wanted to renovate Corsignano into a utopia capable of matching the wonders of other Renaissance towns popping up all over Italy and the world.

Turning to Bernardo Rossellini – a Florentine Renaissance man himself – tons of travertine were brought in to transform the central square – Piazza Pio II – via new advances in math, humanist ideals, and architecture. With the foursome of Palazzo Piccolomini, the Duomo, Palazzo Vescovile, and Palazzo Comunale, Corsignano would now be a new urban wonder.

Since then, Corsignano inherited its new name, Pienza, literally meaning, “The City of Pius.”

Things To See & Do in Pienza

1. Piazza Pio II: The Center…of the Center

Piazza Pio II is the heart of Pienza. From this square, you will find a galore of dining tables and chairs in one of many side streets from the square, all with welcoming hosts ready to serve you a bite of Pienza’s local cuisines and tastes.

It is also a place for moments and photo albums. Palazzo Piccolomini, the Duomo, Palazzo Vescovile, and Palazzo Comunale form a square ring here and grace you with a good visual of what urban architectural reformation looked like in the Renaissance. Add the stone fountain and the tiny flower garden in the center and you are left with a square filled with beautiful architecture, sand and cream-colored columns, and an outgoing community.

2. Palazzo Piccolomini’s Panoramic Views

Palazzo Piccolomini was also built by Bernardo Rossellino and while I am not sure when the small botanical garden was added, the view of the Val d’Orcia beyond is almost certainly the best thing about the palace.

It was built to be a palace, but to my eyes, it felt more like one of those monasteries set aside for quiet contemplation.

I found that the Pienza Pass grants you access to several others of Pienza’s offerings; I’ll let you find out which! August being the busiest time of the year, I would advise avoiding this season since Val d’Orcia then is bustling with visitors.

3. Duomo di Pienza’s Mysteries

The Cathedral is a Romanesque structure whose outward façade was modeled after the Renaissance style in the 15^th century.

How can you tell?

The outside tricks you into thinking the large, window-like recesses are windows when in reality they are walled off. In fact, the octagonal, cuspidate bell tower has that squatness I feel is familiar among Gothic and mostly Romanesque structures.

From the inside, however, it is like an architectural puzzle and a marvel; perhaps the very idea of mysteriousness that was intended with its remodeling? It is all thick columns, no windows, vaulted ceilings, and august majesty.

An interesting note: when writing this, I found that the Bell Tower was an inspiration from Germany brought over by Pope Pius II, not a Gothic structure. And the crypt has several tapestries from Fleming, with the labyrinth a loopy 30-minute walk around the Cathedral’s drainage tunnels. Be sure to book a guided tour to get the most accurate info!

4. Pienza’s City Walls

The walls of Pienza were the prettiest part of Pienza, not for their beauty or grace – of which I am sure they have – but for their view of Val d’Orcia beyond. East of the town between Pienza Cathedral and Porta al Ciglio has this view of the valley you will want to carry away with you on a photo reel or memory card, and the benches around will be sure to give you a rest if you want to take the entire valley in quietly.

Interestingly, the walls also have a Via Dell’Amore! There is a spot where you can see the Cathedral’s spire before the path begins winding around. I think it is because of its secretiveness that lovers were encouraged to frolic around this spot on the wall.

All in all, my tour guide told me stories about the valley’s history and culture, and with how beautiful the valley is, I found myself being taken in by the rolling tapestry he wove.

5. Pienza’s Corso il Rossellino and Other Lovely Streets

The streets of Pienza are a beauty to walk and the next thing you should do coming from the walls.

Via Dogali, Via del Giglio, and Via della Volpe are really lovely; either the residents or city managers have encouraged the streets to be covered in flowers and vines crawling all over doorways. Some double as commercial shops, with lamps on ornate hooks hanging over the doors, and a ware or two out on display. La Vecchia Bortega and Lorto di Silvia were some of them, but more on this later.

On the side street leading off onto the Via Dell’Amore is a wine shop. I spent some time wondering whether there was a wine window in place – having had an adventure seeking them out in Florence – and I think it could be a fun time trying to find them in Pienza.

6. Cheese, Cheese Tasting and Pecorino di Pienza Cheese!

It should be right about lunchtime and whether you are on a guided tour of Pienza’s Dairy Farm Tour with Pecorino Cheese Tasting, a day trip from Florence, or staying in the town, trying out the local food recipes should be one of the most awesome things to do in Pienza.

The cheese is from sheep’s milk, sometimes seasoned with tomato juice and taken with Tuscan wine and cured meat.

La Bottega del Naturista on Corso il Rossellino, 16 felt like the cheese factory of the world despite their small operation. They season their cheese with pignoli, basil and chilli, honey, hay and ash, pasta, truffles and porcini!

PS: I learnt from the Cheese and Wine Tasting Tour that different cheese goes well with different honey and wine!

Via Condotti 1 has the La Taverna del Pecorino that allows cheese tasting and sampling at a very low cost too.

Pienza’s food scene and culture is deep and varied and if it were not for my shoestring budget, I would have taken them all down!

7. Of Gladiators and the Fields of Elysium

Remember that scene in Gladiator (2000) when Maximus (Russell Crowe), wounded and bleeding, starts to imagine his family receiving him after a long time away from home? Then Hans Zimmer and Lisa Gerard begin “Now We Are Free”?

Yes, this is where it was shot.

The locals call it the “Gladiator Viewpoint” and that long walkway with the Tuscan hills in the background really does create that sensation of fading into the distance.

8. Graceful Chapel of the Madonna di Vitaleta

Another site reminiscent of Gladiator is the location of the Chapel of the Madonna di Vitaleta. It is located on a hill just outside Pienza, complete with rows of cypress trees flanking her, blooming flowers on the grassy knoll, and a backdrop of Tuscan hills to the rear.

Inside is a statue of the Virgin, sculpted by Andrea Robbia from the 16^th century – now in a different Church in the same valley -, and the church itself a remodeled effort by Giuseppe Partini. I meant to ask who sponsored the small chapel, but got distracted and only remembered I missed the detail while writing this.

I found most of the small crowds here interesting; couples!

Anyways, the trail up to the church can be a little something Mother Nature has left for her most ardent followers. There are olive groves on the SP 146 to keep you company if you are alone or with a tour group. Or if you are coming from Pienza you can head to the Parish and take the back road.

9. Church of San Francesco’s Creaky Wooden Beams

Fear not; they may look old and creaky, but word is they are really sturdy and fresh.

This is like the oldest church in the town, a Gothic monastery as magnificent as the valley. History has not been kind to the church however; historically filled with frescoes by Cristoforo di Bindoccio, time has worn most of them away, leaving pitifully small vestiges behind. What remains are paintings from Matteo Balducci and Bartolomeo Bulgarini, both of the Virgin Mary and an altarpiece.

And the gorgeous mosaics of the vaulted ceilings and walls of the apse, and the wooden beams up ahead! I think it used to be a stone vault, but the weight of older Romanesque and Gothic vaults used to collapse under their own weight back in the day. In any case, a wonderful lesson in architecture and history if with a tour guide.

10. An Even Older Church in the Pieve di Corsignano

Supposedly built over a different 7^th-century church, the Pieve di Corsignano is where Pope Pius II was baptized. I think this is the reason they left much of its old foundations and structure in place; an honor reserved for the Pope.

The structure is Romanesque, with someone telling me it was Lombard in influence because of the mullioned windows, the double-tailed siren at the main door, and the cylindrical bell tower. Inside are the same wooden beams supporting the roof, and the columns are a very uncharacteristic square shape; sturdy and low. The church is a window into how old Churches were built before influences from the French and Lowlands intruded, and just studying the embossed sculptures is a marked difference from what you will see elsewhere.

11. Artisans and Crafts from Pienza

The ceramics in Pienza are lovely gifts and souvenirs to remind you of your trip. Dining sets, coffee cups, and even daring tea sets can be found here.

What you will find unique about these little gift packs is the paintings of the Tuscan countryside on the ceramics. Many look like the monasteries and chapels on hills in the surrounding countryside. They show the chapel with towering cypresses, blooming red flowers on their grassy knolls, and a gorgeous creamy sky.

There are quite several ceramic shops and stores and I found it an interesting adventure just trying to see whether I could note the distinctive styles of their creators. Try shopping around Ceramiche Bai Linda on Via Gozzante, 33, Ceramiche D’arte Barbieri Silvia on Piazza Martiri della Liberta, 5, and the doll-like statues of Terrecotte Artistiche Pientine on Strada statale 146.

Artemisia Gallery on Via Elisa 5 is an interesting art gallery that lets you buy local paintings of the Val d’Orcia countryside.

12. Cooking Classes in Pienza

There are also a number of cooking classes competing with the artisan scene in Pienza. Preparing dough, pasta, and traditional recipes are offered all with panoramic seasonings of the valley outside. I love that the chefs insist on local, organic produce from the farms around them. Then they share the traditional recipes from their own families. All in all, good experience of things to do in Pienza.

13. Romantic Hot air balloon flight

Quite costly, but for half a day, you and the rest of your traveling companions will enjoy an hour of Val d’Orcia from the sky above.

They let you carry wine on board, and you should be there in the early morning hours because the winds then are not so fearsome. I felt the experience was best when with a private tour group simply because of the shared joy of gazing at the country below.

14. Hiking, Driving, and Riding across Tuscany

Another unique experience you usually get with the advice of tour companies is experiencing the Tuscan countryside on a Vespa, a mountain bicycle rented out, or a vintage Fiat 500!

If you opted for a walking tour, you should try the pilgrim route around La Verna. The driving distance to La Verna is good for a day tour of Florence, Siena, or Pienza itself. Then the 8 km walk around the Franciscan Sanctuary along a route filled with beech trees and mountain air.

These experiences are meant to let you take in the Tuscan air and fragrances from olive groves around you.

Where to Stay in Pienza

1. Hotel San Gregorio is where I stayed for the private parking, pool, and wonderful service. They also accommodate disabled persons pretty well, a group I have regrettably ignored in my blogs.
2. Agriturismo Il Macchione is on my list because of its gorgeous pool overlooking the natural park and is some 2 km from Pienza, making her quite quiet and peaceful at night.
3. A440 in Tuscany is a modern setup complete with a small lake-like pool, shared lounge, and garden.
4. Borgo Sant’Ambrogio – Resort has a sun terrace and garden fitting for an evening away from the crowds outside.
5. Relais Il Chiostro Di Pienza is a convent right in the heart of Pienza, coming with a beautiful pool and commanding view of the valley.

F.A.Q.s about Pienza

1. How much time should I spend in Pienza?

If on a day trip from Rome, Florence, Siena, or Milan, just half a day. With 2 days though, you can take your time and even join a cooking class here or there.

2. How is the weather in Pienza in general?

3b Meteo generally gives the best information for daily weather in Italy. April to May is perfect, or September to October. November – March sees lesser crowds so if you like solo missions this is the time.

3. Do I have to make Dinner reservations?

Reserve in advance during the peak summer season.

4. How do I get around Pienza?

Pienza has no train stations. The trains from Florence, Rome, Milan, Siena, etc stop at places like Torrita di Siena in Siena where you then transfer by taxi, etc

5. Is there parking in Pienza?

Yes. Pienza is private and car-friendly, letting you approach the town. Punto Sosta Comunale (Parcheggio Pienza) on Via Mario Mencatelli, 40 just 5 minutes from the Piazza was our parking spot. There are many other parking spots though, like Via del Cassello parking at Viale di Circonvallazione, 25.

6. Are there Tours of Pienza?

Most people I came across went for this option. Save for blogs like my own where we try to get as much out there as we can, tour groups will offer you an in-depth view of Pienza.

7. Which is better, Pienza or Montepulciano?

Montepulciano is better known for its wines, while Pienza’s cheese takes the cake. Pienza is also smaller, so less to see, but quieter, prettier and also better to stay in.

8. Which is better, Pienza or Montalcino?

Montalcino has better wine, while Pienza’s cheese is better. Both have great views of Val d’Orcia though, so it’s a coin toss.

9. Are the shops, restaurants, and sites open on weekends?

Yes.

10. Is Tuscany safe for solo female travelers?

Absolutely Yes! I live in Italy with my family and 90% of the time I tour not just Tuscany but Italy in general solo. I’m a young black (if this helps emphasize) & ”hot” female.

11. Can I book a tour of the area?

Yes. Summers can be crowded, but manageable. Booking in advance around this time can be restrictive because then your itinerary is locked and you cannot do side missions.

I’ve traveled to many regions in Italy, and I can safely say that Tuscany comes in at 2^nd place after Lazio of course, why, because Rome is in Lazio, Rome, the Eternal City is a city of dreams! Rome is justified to take 1^st place, I mean, there’s the 2000-year-old COLOSSEUM! being the largest Amphitheatre in the world and still standing!

Then there’s the majestic all-gods PANTHEON! For the love birds, there’s the TREVI FOUNTAIN (I live in Italy because of the “Trevi legend” 🤤)! For the ancient ruin lovers, there are the ROMAN FORUMS! As for the lovers of arts and sculptures, Rome has the FOUNTAIN OF FOUR RIVERS, the beautiful PIAZZA’S ( Squares) to just chill, Rome’s got you covered ….. guys, I could really go on and on shamelessly without tire, but we are here about Pienza in Tuscany. If you feel me, check my YouTube Channel on everything Italian, and then you’ll feel exactly what I feel.