Discover Tuscany's towns and villages across three distinctive landscapes: the tufa country of the Maremma, the Renaissance heart of the Val d'Orcia, and the upper Tiber valley near Arezzo. Compare their character below and choose which area to explore.

| Place | Area | Terrain | Known for |
|---|---|---|---|
| Pitigliano | Maremma | Hilltop, tufa cliff | Built into the rock face; the "Little Jerusalem" synagogue quarter |
| Sovana | Maremma | Hilltop, tufa cliff | A quiet frazione of Sorano above an Etruscan necropolis |
| Pienza | Val d'Orcia | Hilltop | Planned Renaissance town centre, UNESCO-listed since 1996 |
| Anghiari | Valtiberina | Hillside | Medieval streets above the plain of the 1440 battle associated with Leonardo da Vinci |
Pitigliano — Pitigliano rises straight out of a tufa cliff above the Lente river, its houses continuous with the rock they stand on. The town's old Jewish quarter earned it the nickname "Little Jerusalem."
Sovana — Sovana is a small frazione of Sorano in the Maremma's tufa landscape, with an Etruscan necropolis carved into the surrounding rock.
Pienza — Pienza was transformed from the village of Corsignano starting in 1459, when Pope Pius II commissioned Bernardo Rossellino to reshape his birthplace. Its Renaissance centre, including Piazza Pio II, has been a UNESCO World Heritage Site since 1996.
Anghiari — Anghiari overlooks the upper Tiber valley near the Umbrian border and the plain where the Battle of Anghiari was fought in 1440. Leonardo da Vinci was later commissioned to depict the battle.
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Pitigliano and Sovana are about 3 km (straight line) apart in the Maremma's tufa landscape. This is a straight-line distance, not a road distance.
Pienza is about 50 km (straight line) from Pitigliano. This straight-line distance is not a road distance. Pienza belongs to the Val d'Orcia, a different area from the Maremma tufa towns.
Anghiari is about 60 km (straight line) from Pienza. This straight-line distance is not a road distance. It belongs to the Valtiberina near Arezzo and Sansepolcro; plan this area separately from the Val d'Orcia and Maremma.
Explore each village page for its location, sources, nearby places and accommodation options.