Pienza town center

Pienza — we have a long-standing love affair with this lovely medieval hill town in the province of Siena in Tuscany.

Pienza is often called the “touchstone of Renaissance urbanism,” is situated between Montepulciano and Montalcino. It offers a fantastic view over the beautiful Val d’Orcia and is smaller and more intimate than its 2 more well-known neighbors.

The town owes its beauty to the fact that in 1459 Pope Pius II had the entire village, his birthplace, rebuilt as an ideal Renaissance town. In 1996, Pienza was declared a UNESCO World Heritage Site and in 2004 the entire valley (Val d’Orcia) was included on the list of Unesco’s World Cultural Landscapes — it’s that beautiful!

Not only is the town itself a wonderful photographic subject matter but within 30 minutes by car, you will find some of the most iconic images in all of Tuscany.


View of Pienza from a field below the medieval walls

View of Pienza from a field below the medieval walls

Yes, this grove of cypresses has been photographed a million times and has been used so often in ads and commercials worldwide that it is now copyrighted (!) but the fact remains that this location is simply stunning and inspiring. It looks different each year, each season, each day and hour and is so photogenic that we’ll keep returning to this “old friend” year after year.

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The “copyrighted” cypresses just outside of Pienza

Pienza is the town we base our Tuscany Photography Tour out of but we also love just hanging out there for a week or so every year.

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Charming doors, windows, squares, and churches to photograph

There are so many great places to stay  — from elegant hotels to cozy B&Bs. Many of these places offer incredible breakfast buffets and in some cases, you can fill a whole book just photographing the view of the magical Val D’Orcia right out of your hotel window.

Our favorite is a charming small medieval B&B  that’s surrounded by beautiful flowers and hidden behind a tall stone wall. We have also greatly enjoyed staying at Benedetto’s simple but cozy B&B where he treated us to the best bruschetta ever — and it’s so simple.

Benedetto’s Bruschetta

Benedetto toasts thick slices of white crusty bread, rubbs them generously with peeled garlic cloves, then soaks them in his father’s thick bright green and deliciously bitter olive oil (use the thickest and best olive oil you can get your hands on) and sprinkles it with coarse salt — HEAVENLY!


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And since we’re on the subject of food: Pienza’s most famous product is the delicious Pecorino sheep cheese. Walking along Pienza’s main street, you’ll experience the spicy scent of Pecorino in its many stages of ripening wafting out of beautiful specialty food stores stacked to the ceiling with rounds of pecorino, salamis, prosciutto, wine, and noodles in every imaginable shape. In this photo you see Larry, one of our Tuscany Photography Tour participants, having fun with cheese.

There are also so many great places to eat — you’ll discover your favorites — but here are some of ours: Trattoria Fiorella (run by 2 charming brothers), Trattoria Latte di Luna with lovely outdoor seating, Trattoria La Buca delle Fate with its beautiful vaulted ceilings, the Piccolomini Caffe for great coffee and lunch, the fairly new La Bandita Townhouse Caffe which offers modern Italian with wonderfully fresh local products and, best of all, the Osteria La Porta in Monticchiello, a tiny town just minutes from Pienza where Daria has definitely earned her Micheline stars.

Stay tuned for more on the stunning Val D’orcia and its iconic photo locations.

Happy shooting,

Jim + Magrit