Curator’s statement
Tuscany is a region of Italy with so many discoveries to fall upon — small hill towns like Monteriggioni and Pitigliano, stunning vistas and local specialties. It's a place to take your time, enjoy picnics overlooking the rolling hills and treat yourself to vin santo at the end of a fabulous dinner. I studied in Siena decades ago and continue to return year after year. I've curated a short list of my favorite Tuscan specialties and where to find them.
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Where to stay in the Tuscan Hill Towns
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Things to do in the Tuscan Hill Towns
I’ll start by sharing that, while I appreciate the talent, commitment and training inherent in achieving a Michelin star, my preferences tend to be more casual in nature — a picnic lunch hosted by cheese farm in the rolling hills of Tuscany; a family-run, bustling restaurant in the shadows of Siena’s Palazzo Pubblico or mouth-watering pizza in Montepulciano.
Places to eat & drink in the Tuscan Hill Towns
Pecorino di Pienza
First, let’s talk pecorino, which rivals Parmigiano Reggiano — produced in the provinces of Parma and Modena — in flavor and tradition.
Pecorino cheese from Pienza — often referred to as "Pecorino di Pienza" — is renowned for its high quality and distinctive flavor. It hails from the picturesque village of Pienza, located in the Val d’Orcia region of Tuscany. The town has lush, aromatic pastures and rolling hills providing ideal conditions for raising sheep and producing high-quality milk. Pecorino is often produced by small, artisanal dairies that follow age-old methods, ensuring the preservation of its unique qualities. In fact, to ensure its quality and authenticity, Pecorino di Pienza has received recognition and protection under European Union regulations, often enjoying Protected Designation of Origin (PDO) status.
Where to enjoy Pecorino di Pienza:
Latte di Luna, Pienza: Located in the historic center of this sublime hill town, Latte di Luna will keep you coming back for more. Order the pici cacio e pepe, made with fresh pasta and cheese sourced from the hills just a few kilometers from its kitchen. Another unforgettable dish? The pappa al pomodoro.
Cugusi Dairy, Pienza & Montepulciano stores: With over 60 years of family-run production, Cugusi Silvana Caseficio is an icon in the region, responsible for award-winning cheeses that have gained international notoriety. You can purchase any type of pecorino — from fresh to aged — as well as fresh daily options including ricotta and yogurt from their shops.
Cugusi, Montepulciano Farm tastings: Beneath the Tempio of San Biagio in Montepulciano, you can enjoy tastings at Cugusi’s dairy farm tasting room in the most beautiful setting. You’ll taste the various varieties of pecorino di Pienza — accompanied by a glass of Rosso di Montepulciano.
Cugusi, Montepulciano Farm picnic: Don’t miss the opportunity to enjoy watching sheep graze under the shade of a pergola with a picnic basket of Cugusi’s finest selections of cheese. They’ll give you a cutting board and cutlery to use and you’ll also get your pick of locally cured meats, fresh bread, fruit compotes and wines from the best cellars of Montepulciano. You pay as as go — this could be one of your favorite food experiences in the hill towns.
Pappa al pomodoro
Pappa al pomodoro is another quintessential Tuscan dish that exemplifies the region's culinary philosophy: making the most of simple, high-quality ingredients — and some leftovers, like stale bread — to create dishes that are both delicious and comforting. This dish is a prime example of the Tuscan tradition of "cucina povera" or "poor cuisine,” but it is nothing short of rich in flavor and taste. In addition to day-old bread, the ingredient list is basic: tomatoes, olive oil, garlic and basil.
Where to enjoy pappa al pomodoro:
Ristorante La Finestra, Siena: I’ve been close friends with the proprietor, Carla, and her family for over three decades, yet every visit to La Finestra is more delightful than the last. Don’t miss this iconic Sienese restaurant — a few paces from Il Campo. It’s Classic Tuscan cuisine at its finest. The specialty board changes daily, but nearly always includes pappa al pomodoro, an incredible assortment of crostini, grilled meats, fresh pasta and truffle dishes, another specialty of the region. In short, La Finestra is a "don’t miss” for a leisurely lunch or fantastic dinner. The outdoor covered patio is so lovely and the inside rooms are beautifully decorated with Sienese ceramics and historic photos.
Truffles
Both black and white truffle (tartufo) varieties are very rare, only turning up in a few areas of the world. Luckily for visitors to the region, Tuscany has both growing in its hills. Whether tagliatelle al tartufo, risotto al tartufo or meat adorned with this incredible sauce, you’ll find this culinary treasure incorporated into so many “order seconds” dishes. Tuscany has several areas renowned for truffle hunting, including San Miniato, Volterra and the Crete Senesi near Siena. San Miniato is famous for its white truffles and hosts an annual festival in November that attracts foodies from around the world.
Where to enjoy truffle dishes:
La Taverna di Cecco, Siena: This spot serves veal carpaccio with truffle, risotto with truffle and a single crouton al tartufo — order one for yourself because you won’t want to share. Located on a narrow side street in Siena, this small restaurant is a great place for a casual meal.
Le Terrazze del Palagetto, Volterra: Located inside Il Palagetto — a bed & breakfast — and treats diner with panoramic views over the hills of Volterra. The restaurant’s menu includes a creamy pici pasta topped with fresh truffles and cuts of beef with a creamed truffle sauce. Don’t miss the Tuscan pecorino infused with truffle. Tip: Make sure to have your GPS in check as there are a few twists & turns.
Pizza
While Tuscany is not necessarily known for pizza, there are a few pizzerias in the hill towns that keep me coming back for more.
Where to enjoy pizza in the hill towns:
Lie Viti, Montepulciano: This spot serves incredible Neapolitan-style pizza. Don’t miss the classic Margherita with Buffalo mozzarella.
'O Scugnizzo, Arezzo: This ranks among one of the best pizzerias in Tuscany. Founded by Caserta-born pizzaiolo Pierluigi Police and his family. So many exciting options including friend pizza, but don’t miss the Pizza Presidio with ingredients from Campania including Castelpoto red sausage, papaccelle (sweet peppers), provolone and Roman tanned cheese.
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Rebecca Hanson
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This guide is part of our ongoing series on travel to Italy. Looking for more travel inspiration? Check out my guide, Slow Travel through the Tuscan Hill Towns.