Spending a full weekend in Pitigliano means diving deep into the beauty and unique charm of this “city of tuff” and experiencing its three main souls: historical, natural, and gastronomic. A great way to organize your stay is to dedicate one day to the historic center and its museums, and the other to exploring nature and local trails.
Assuming you arrive in the late afternoon, once you’ve settled into your accommodation, you can enjoy a breathtaking sunset, sip an aperitivo, and have dinner in one of the many local spots, each with its own character and story.

Day one

The next morning, after a good breakfast, there’s nothing better than a long, pleasant stroll through the old town. Wander through charming piazzas, narrow alleys, and discover monuments at every turn. Starting from Piazza Petruccioli, right at the entrance to the center, you’ll naturally follow a route that takes you past all the main sights: Via Cavour with its Medici aqueduct, Piazza della Repubblica with Palazzo Orsini, and Via Roma (the main street), which leads to Piazza San Gregorio VII, where the Cathedral stands. From there, head down to the oldest part of town known as Capisotto.
To return, you can take Via Vignoli (also known as La Fratta) or Via Zuccarelli, which passes through the Jewish quarter. Here, you’ll find important remnants of the historic Jewish community, such as the Synagogue, the matzah oven, the Kosher butcher, and wine cellar.

Throughout the oldest part of the village, you can also discover glimpses of Pitigliano’s underground world—an impressive network of monumental cellars and tunnels carved into the tuff rock. For a deeper dive, we recommend joining a tour with one of our certified guides.
By this point, it’ll be time for lunch. Choose one of the many restaurants and try some local specialties—there’s plenty to tempt your palate.

In the afternoon, explore the town’s exhibitions and museums. Three are located in the old center, two within Palazzo Orsini and one in the Jewish quarter. Each museum highlights an important era in Pitigliano’s long history. At Palazzo Orsini, you’ll find the Civic Archaeological Museum of Etruscan Civilization “Enrico Pellegrini” and the Palazzo Orsini Museum. The building also houses the Town Library, which is worth a visit. In the Jewish quarter, explore the Permanent Exhibition of Jewish Culture. Each museum takes about an hour to visit, and again, we suggest a guided tour for a more enriching experience. Afterward, enjoy some shopping in the local boutiques and artisan shops.

As evening falls, Pitigliano’s lively spots come to life: cafés, wine bars, and lounges where you can enjoy an aperitivo with local wines or sip a well-crafted cocktail. For dinner, you’ll be spoilt for choice with restaurants, trattorias, and pizzerias to suit all tastes.
Before calling it a night, make sure to see Pitigliano lit up after dark—it’s magical. You can admire the view from two main panoramic points outside the center: the garden terrace on Via San Michele (within walking distance), or the square in front of the Madonna delle Grazie church, about a kilometer from town. Don’t forget to snap a photo!

Day two

La seconda giornata si può dedicare alle bellezze naturalistiche e storiche presenti fuori dal centro. Se siete appassionati di trekking potete provare il Tour delle Vie Cave che vi farà visitare, in un’unica passeggiata, tutti questi luoghi fantastici che caratterizzano Pitigliano e dintorni, accompagnandola magari a un picnic. Per maggiori informazioni consultare la sezione dedicata al Tour delle Vie Cave che, se svolto per intero, vi occuperà circa metà giornata; potete anche scegliere di visitare una o più Vie Cave a seconda del tempo a disposizione.

In the afternoon, head to Pitigliano’s open-air museum—the “Alberto Manzi” Archaeological Park. Here, you’ll discover another fascinating Via Cava, the Gradone, not included in the earlier tour.
Alternatively, for those who love local flavors, spend a couple of hours in one of the many wineries or farms scattered across the Pitigliano countryside. Enjoy a glass of wine and taste the best local produce in an authentic setting.

Before you leave, don’t miss out on a few culinary gems you’ll find in town: pici (handmade thick spaghetti), acquacotta (a rustic vegetable soup), and sfratto, the traditional Pitiglianese dessert made with walnuts and honey. And of course, everything tastes better with a drizzle of local extra virgin olive oil—another Maremma treasure.