Finding Good Fortune, a Kiss, and (A)More in Pienza!

September 19, 2012 / Places
Pienza, Tuscany
The lovely hilltop village of Pienza is a short (approx. 60 kms.) and worthwhile side trip from Siena. As the birthplace of Pope Pius II, this tiny town received many favors (including renaming it after himself!). His intention was to make it a model Renaissance town and today it has the distinction of being a UNESCO World Heritage Site.

Although you could “see” Pienza in an hour or so (made all the easier since it’s strictly pedestrian), it deserves more than a quick visit. Take time to visit and enjoy the friendly artisan shops and trattorie (put tasting pecorino cheese on your list of things to do here!). It’s impossible to get lost, so accept the invitation to just meander and stroll along the gently winding alleyways. Welcoming and well tended window boxes and flowerpots bursting with color greet you everywhere.

Be sure to find the walkway along the city walls where you will delight in a breathtaking view of the patch worked Val D’Orcia below. Doubtless you will notice some of the intriguing street names: Via Bella Fortuna, Via del Bacio, Via dell’Amore. Not only are they fun photo opportunities, but one can’t help but wonder about their origin. Is there a local story or legend? Is there a traditional ritual to do? Should we make a wish? You’ll have to decide for yourself!

Victoria De Maio

by Victoria De Maio

Victoria is a lover of all things Italian! A travel advisor, blogger, writer, tour leader, and published author, she is passionate about traveling to and writing about Italy.

Her book, Victoria’s Travel Tipz Italian Style, is available on Amazon.

Join Victoria for her fabulous unique, boutique tours of Puglia,, and the Italian Riviera.

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27 Responses to “Finding Good Fortune, a Kiss, and (A)More in Pienza!”

  1. Marilyn Gentile

    One of many reasons to fall completely and utterly in love with Italy-so beautiful!

  2. Joseph Mattei

    My wife Susan and I were there a couple of years ago. We loved it. Also it is located within easy driving to many places for exploring Italy!

  3. john o'connor

    Visited this beautiful town while a celbration was taking place in which magnificant floral displays were created on the walkways. Don’t recall what the occasion was. Also, wasn’t this the town featured in the movie “The English Patient.” Forgive me if I have the title of the movie wrong.

    Welcome Victoria and Ciao Tutti!

  4. Kathryn Piersanti

    Thank you Victoria for doing a story on Pienza….my favorite hill town in all of Tuscany. I have had many dinners at Latte di Luna! My nephew was baptized in Montepulciano so you have brought back many years of wonderful experiences we have endured in Pienza!

  5. Giuseppe Spano
    Giuseppe Spano

    Thank you Vittoria, this is Italy or what one would wish all towns to be,peaceful,beautiful. A beauty of times past…

  6. Mickie Proud

    Welcome. Already, you are a wonderful contributor. I look forward to many more of your notes.

  7. Marianne Bevilacqua

    Thank you for writing about this beautiful town in the Val d’Orcia. My husband and I visit Italy every year and stay at an Agriturismo close by. We can literally “See Pienza” from our window. We too have had many a delicous meal at Latte di Luna in the center of town. We can’t wait to return!

  8. I’m thrilled to have my first submission printed and thrilled to share memories of Pienza with all of’s one of those places that never ceases to delight!

  9. What a beautiful town!! Aaaah. Tuscany. These gems seems endless. Thanks for the morning coffee and photo walk around Pienza. :)

  10. Laura LaGris

    Congratulations. This is wonderful and such a joy for you to share this beautiful place with so many.

  11. Rita Mantone

    We will be here in a couple of weeks!!! The owners of Agriturismo Cretaiole live in Pienza. They are wonderful people with an amazing farm stay in Tuscany!!!

    I am so glad this article came out now, it is making me very excited!!!

  12. Arden Fowler

    My favorite trattoria in Pienza is La Buca della Fate. Love their peperoncini arrosta and pici con salsa cinghiale. Don’t forget to buy dried herbs, fragrant soaps and sachets in this delightful town, or go to a concert in the courtyard of the Palazzo Piccolomini.

  13. Barbara G

    I had the pleasure of visiting this absolutely lovely village this past May. It is by far the most perfectly idyllic of all the villages that I have thus far visited. It’s history is as charming as it’s many buildings and quaint shops. I cannot wait to go back and spend more time there.

  14. Domemic Piccolomini


    Thank you so very much for posting this note. My wife and I Spend 5 to 7 days here each year in late May early June. Over the past 10 years we have taken many of our dearest friends, relatives and family with us, they all love this village. We also meet our Italian cousins here and they all love coming to Pienza as well. It is truly our favorate place in the world. Peaceful, tranquil, the most beautiful view anywhere. We stay at the Piccolo Hotel which has a beautiful view from our balcony. We dine at Dal Falco and Latte de Luna. Pienza is also a great location for a home base as it is located with in 1 hr. drive time to many other hill towns in Tuscany and Umbia.

  15. Amici! I love all of your notes…obviously Pienza is a favorite with many of us. I also love all of the insights on where to stay and where to eat…I’m ready to go back!

  16. Gloria Kawiecki

    How beautiful and quaint. My parents were born in the Province of Lucca, Tuscany. I’ve been to Italy twice and plan to go next May 2013. I LOVE all Italy. Wish I could live there>

  17. For those of you who will be visiting Pienza, I would also like to recommend another wonderful osteria, Sette di Vino…Luciano is your charming host..I can’t wait to return and sample all of the other wonderful suggestions!

  18. Cheryl Bradbury

    Oh, Pienza! I have stayed at Agriturisimo Cretaiole twice in the last years and have enjoyed all of those eateries aforementioned. La Buca has the best chickpea soup ever! There is much history here and the sweeping views of the valley of the Val d’orcia are unsurpassed. I have traveled much of Tuscany and Pienza is my favorite but perhaps because of the warmth of the family that own Cretaiole where we stay.
    Thank you for showcasing this delightful part of paradise.

  19. Bob Reardon

    Thanks for sharing the place and the feelings ! My favorite is the picture of the ladies sitting and visiting with each other. AAAHH Relaxation !

  20. Beth Patterson

    We were there this past Sunday and there was a 5k race involving three little geese. Any idea the symbolism of the geese? We guessed it had something to do with Pope Pio, but cannot find anything. They were placed in a pen where runners were signing up.

  21. I’m so pleased that so many of you are still enjoying my “premiere” article. As for the symbolism of the geese, Beth, I have no idea but will definitely report back if I come across any revelations.
    Gloria, my mother’s mother was born near Lucca as well and although I have been to Lucca, the visit was never long enough so I look forward to exploring more of the region soon as well.


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