Perched atop Tuscany’s highest points, these ancient stone settlements command breathtaking views across Italy’s most celebrated landscape.
Once built for defense, these dramatic Tuscan hilltop towns now reward travelers with winding cobblestone streets and historic architecture.
Here are 8 spectacular hilltop towns in Tuscany that deserve a place on your Italian adventure.
The 8 Most Dramatically Positioned Tuscan Hilltop Towns
Here are 8 of the most spectacularly positioned Tuscan towns that deserve a place on your Italian journey.
1. Pitigliano
Located in southern Tuscany, Pitigliano rises vertically from massive tufa cliffs, creating one of the most striking silhouettes in Italy.
Explore the historic Jewish quarter, known as “Little Jerusalem,” with its restored synagogue and museum.
Don’t miss the network of underground passages carved into the tufa rock of this hidden gem in Tuscany.
2. Montepulciano
Set along a limestone ridge in southeastern Tuscany, Montepulciano offers views of both the Val d’Orcia and Val di Chiana.
Visit historic wine cellars tunneling beneath Renaissance palaces to taste the famous Vino Nobile.
The town’s main street climbs steadily, revealing impressive architecture including the Palazzo Comunale and Cathedral of Santa Maria Assunta.
3. Sorano
Rising from tufa cliffs in southern Tuscany, Sorano is often called Pitigliano’s “wild sister.”
Hike the ancient cave-carved pathways called “Vie Cave” and stay in accommodations built directly into the cliff face.
Nearby natural hot springs offer relaxation after exploring.
4. San Gimignano
Located between Florence and Siena, San Gimignano is famous for its medieval towers that create a distinctive skyline. Of the original 72 towers, 14 remain standing.
Climb the Torre Grossa for panoramic views and visit the Collegiate Church with its remarkable frescoes.
The central Piazza della Cisterna is perfect for sampling the local Vernaccia white wine.
5. Volterra
Perched on a high plateau in western Tuscany, Volterra is surrounded by Etruscan walls with views extending to the coast on clear days.
Visit the archaeological museum and watch alabaster craftsmen in their workshops.
The well-preserved Roman theater just outside the medieval walls ranks among Italy’s best ancient sites.
6. Cortona
Positioned on a hillside in eastern Tuscany near the Umbrian border, Cortona overlooks the Val di Chiana valley and Lake Trasimeno.
Made famous by “Under the Tuscan Sun,” the town features the excellent Etruscan Academy Museum and Renaissance Santa Maria Nuova church.
Its steep streets lead to restaurants serving local specialties and distinctive Syrah wines.
7. Pienza
Perched on a ridge overlooking the Val d’Orcia, Pienza was transformed from a village into an ideal Renaissance city by Pope Pius II.
This UNESCO World Heritage site features perfectly preserved Renaissance architecture, including Palazzo Piccolomini with its hanging gardens.
The town is renowned for its pecorino cheese and offers iconic Tuscan landscape views.
8. Anghiari
This walled town on a slope in eastern Tuscany overlooks the Upper Tiber Valley where a famous 1440 battle took place.
Explore steep medieval streets leading to panoramic terraces and visit artisan workshops specializing in furniture restoration.
The Palazzo Pretorio provides historical context, while the surrounding area offers excellent cycling and hiking opportunities.
Final Thoughts on the Best Hilltop Towns in Tuscany
Tuscany’s hilltop towns aren’t just places to visit—they’re experiences to collect.
Each town’s unique character and stunning views will leave you planning your return before you’ve even left.
Pack comfortable shoes, bring your camera, and prepare to fall in love with Italy from above.
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