Update: While the crowds are currently elbowing each other for a glimpse of the David in Florence, a city that requires some savvy when it comes to parking, or fighting for a table in Siena, I’ve been drifting further south into the rugged heart of the Maremma, an area that has led me to discover other hidden gems, such as the wild secret heart of the Mediterranean.
Since I wrote this piece, I’ve been letting you in on a secret: the real Tuscany isn’t found in a brochure. It’s found in a place that looks like it was sculpted by giants and then forgotten by time. I’m talking about Pitigliano, a town that embodies the essence of Italy’s hidden gems. If you’re looking for more off-the-beaten-path adventures, my colleague Marco has a wonderful guide to exploring a thrilling road trip through Italy’s Lucanian Dolomites, that will take you through some of the country’s most breathtaking landscapes. Update: I just checked in with Marco, and he’s been working on some new routes and tips – be sure to check out the latest updates in his post.
The Fortress of Tuff#
The first time you see Pitigliano, it takes your breath away. I’m not exaggerating. As you wind around the curves of the SR74 highway, the trees suddenly part, and there it is—a town seemingly erupting directly out of a massive volcanic tufa cliff. The houses are built from the same stone they sit upon, making it impossible to tell where nature ends and the city begins. This unique blend of natural and man-made structures reminds me of other dramatic locations, such as the fortress I’ve explored in detail in my previous travels, where the interplay between architecture and landscape is just as breathtaking.
Update: I’ve since written a guide to Rasiglia, a village that has captured the hearts of so many travelers, which can be found in my newer article about the village of streams – a place that has become one of my favorite discoveries.
My Secret Tip: The Vie Cave (Etruscan Sunken Roads)#
If you want to feel like an explorer rather than a tourist, you have to leave the city gates and head into the ancient pathways carved deep into the rock by the Etruscans, which my colleague Alessandro has beautifully described as a testament to the ingenuity of the Etruscans, over 2,500 years ago.
We’re talking about massive corridors with walls up to 20 meters high, draped in moss and ferns. It feels like stepping into a fantasy novel.
- The Hidden Path: Look for the Via Cava di San Giuseppe. It’s a hauntingly beautiful trek that leads you through the belly of the earth.
- Luca’s Insider Advice: Go at golden hour. The way the light filters through the canopy and hits the yellow stone is pure magic. You won’t find any tour buses here—just the sound of your own boots and the whispers of ancient history.
Little Jerusalem and Authentic Flavors#
Pitigliano is known as La Piccola Gerusalemme (Little Jerusalem) because of its historic Jewish community that found refuge here in the 16th century.
If you want something different than the standard pasta dishes, wander into the old Jewish Ghetto. You can visit the ancient synagogue, but my secret tip is to find a local bakery and ask for a Sfratto. It’s a baton-shaped cookie filled with honey, walnuts, and orange peel. Its name means “eviction,” and it has a rebellious history that I absolutely love—it was shaped like the stick used by authorities to knock on doors during the era of the ghettos, turned into a symbol of sweetness and resilience by the locals.
How to Experience Pitigliano Like a Local#
- Drink the Volcano: Order a glass of Bianco di Pitigliano. The vines grow in volcanic soil, giving the wine a mineral kick you won’t find in a Chianti.
- The Best View: For the ultimate photo (without the crowds), head to the Santuario della Madonna delle Grazie. It’s just outside the town and offers the most dramatic panorama of the skyline.
- Stay Late: When the day-trippers leave, the town turns into a labyrinth of shadows and golden lanterns. That’s when the real soul of the place comes out.
Forget the postcards you’ve seen a thousand times. Pitigliano is for the ones who want to see Italy’s untamed side. It’s raw, it’s rocky, and it’s waiting for you to discover it before everyone else does.
As I’m sipping on a glass of Chianti from the rolling hills of Tuscany, I’m reminded of the incredible wine experiences that await travelers in Italy. My colleague Alessandro has a wonderful guide to exploring Italy’s historic regions, including the birthplace of some of the world’s most renowned wines, which he recently explored in his article about a 2025 wine lover’s grand tour through historic regions - Uncorking Italy’s Soul: A 2025 Wine Lover’s Grand Tour Through Historic Regions.