Pitigliano rises dramatically from a tufa ridge as if carved from it, surrounded on all sides by a deep ravine sliced by Etruscan "ways" they call Via Cave. Pitligliano is located in the Upper Maremma of Tuscany. The town is known as "Piccola Gerusalemme", or "Little Jerusalem" after the large Jewish population settling here in the middle of the 16th century from the south to avoid the Vatican's Counterreformation persecution. You can take an interesting trip underground and see the remains of the older Jewish quarter.
The area is loaded with very interesting and unique Etruscan remains carved out of the soft tufa, besides the via cave there are interesting tombs and carved churches. Put on your walking shoes and explore.
Pitigliano's Jewish Quarter is a must-see. It was a haven for Jews who didn't like the confinement of ghettos in the big cities like Florence and Siena and couldn't move further south into the anti-Semitic Papal States in Lazio. They were eventually driven out by 1938 when the Fascist racial laws were applied. There is a restored synagogue and food processing areas, including a winery, as well as a museum to visit.
To the southwest along the SR74 is a view spot where you might get a picture of Pitigliano like the one above.
Pitigliano, in the Grosseto province of Tuscany, is surrounded by some very nice Italian countryside. While the city is very nice to stroll inside the walls, the real Kodak picture moment comes from outside the city, when you see that volcanic plateau rising from the plains, covered with little stone houses built right to the edge of certain calamity.
Pitigliano is between Rome (140km) and Florence (175km), about 48 km southeast of Grosseto and 25 km west of Lake Bolsena in the Northern Lazio region.
There's no train station in town but buses serve Pitigliano from other cities and towns in Tuscany, including Siena, Florence, and Grosseto (served by train). The town itself is small enough to walk around easily.
A car is recommended for touring the countryside, Etruscan sites, hot springs, and other small towns of the Maremma.
There are many historic walks to take around Pitigliano as well. All this leads me to think that spending some time in a country house, even a week or more, in Pitigliano would be a very good thing to do. VRBO lists 35 vacation rental properties in and around Pitigiano: Pitigiano Vacation Rentals.
Stay in a Palace? Set in Pitigliano’s historic Orsini Fortress, Locanda Il Tufo Rosa is at the entrance to the town’s historic center.
We like the food at Hosteria del Ceccottino very much. Less expensive, but very good is Trattoria La Chiave del Paradiso. Both are in the center of the old town and marked on the map with comments.
Another very interesting option in Pitigliano is a relatively new restaurant called Enoteca La Corte, run by a couple who are art historians. The experience is expertly described in Lambrettas, Lorenzo Lotto and Lunch in Pitigliano.
The Secrets of Pitigliano from sweet pork crackling bread to butterflies.
Eytan Kahn's Pitigliano: the Little Jerusalem