GemmaItaly is famous for its history, food, and breathtaking landscapes, but there’s something truly magical about its hill towns. Nestled among rolling hills, vineyards, and olive groves, these towns are not just picturesque—they are living snapshots of centuries past. From my own personal experience, exploring Italy’s hill towns feels like stepping into a painting, complete with cobbled streets, charming piazzas, and panoramic views you’ll never forget.
If you’re planning a trip to Central Italy, these ten hill towns are must-visits. Each town has its own personality, unique attractions, and hidden gems. Whether you want to wander through medieval streets, taste incredible local cuisine, or simply breathe in some of the best views in Europe, these towns have it all. Let’s dive in.
1. Orvieto, Umbria
Perched atop a volcanic tuff cliff, Orvieto is a jewel in the heart of Umbria. Its cathedral is a masterpiece of Gothic architecture, with an intricate façade that will make your jaw drop. Stroll through the narrow streets, and you’ll discover cozy cafes and artisan shops.
Don’t miss the Orvieto Underground tour—this labyrinth of tunnels and caves carved into the volcanic rock tells the town’s ancient history in a way that’s both fascinating and slightly eerie. From my own personal experience, sipping a cappuccino while overlooking the valley is one of the most peaceful moments you can have in Italy.
2. Civita di Bagnoregio, Lazio
Civita di Bagnoregio is known as “the dying town” because erosion threatens its existence. However, this doesn’t make it any less charming. The town sits dramatically on a hill, accessible only by a pedestrian bridge, which gives it an almost fairytale quality.
Once you step inside, you’ll find quaint streets, tiny squares, and views that seem almost surreal. It’s small, but it packs a punch in terms of beauty. You’ll also find local restaurants serving traditional dishes—try the pasta with truffle sauce, it’s unforgettable.
3. Montepulciano, Tuscany
Montepulciano is a Tuscan gem famous for its wine. The town itself is a labyrinth of Renaissance palaces, medieval towers, and elegant piazzas. Take your time walking through Via del Corso, lined with shops selling handmade goods and local delicacies.
Wine lovers will feel like kids in a candy store here. From my overall experience, booking a wine tasting in one of the historic cellars is a must—you’ll learn about Vino Nobile di Montepulciano and, more importantly, taste it. The sunsets from the town’s walls are also stunning, casting a golden hue over the rolling hills.
4. Assisi, Umbria
Assisi is more than just a religious center; it’s a town full of charm, history, and stunning views. Known as the birthplace of St. Francis, it attracts pilgrims, but it also appeals to anyone who loves medieval architecture.
The Basilica of San Francesco is breathtaking, with frescoes that depict the life of St. Francis in vibrant detail. Wander the cobbled streets, and you’ll find artisan shops and local trattorias serving Umbrian specialties. Based on my overall experience, walking the paths at sunset, when the crowds thin and the light softens, is a moment you’ll never forget.
5. San Gimignano, Tuscany
San Gimignano is famous for its medieval towers, earning it the nickname “Medieval Manhattan.” Walking through its streets is like stepping back in time. You’ll encounter artisanal shops, gelaterias with award-winning flavors, and squares that seem to invite you to linger.
Climb one of the towers for a panoramic view of the surrounding Tuscan countryside—it’s absolutely worth the effort. Let yourself wander without a plan; the charm of San Gimignano is in discovering its little corners. And yes, the gelato here really is as good as everyone says.
6. Spello, Umbria
Spello is one of those towns that feels untouched by time. Its walls are lined with flowers in spring, and the streets are narrow and inviting. Every corner seems to hold a piece of history, from Roman ruins to medieval churches.
Walking here is like wandering through an open-air museum. You can also taste some of Umbria’s best olive oils in local shops. From my own personal experience, the quiet morning walks in Spello, with sunlight filtering through ancient stone walls, are magical.
7. Pienza, Tuscany
Pienza is a Renaissance masterpiece. Designed as an ideal city by Pope Pius II, it’s small but incredibly photogenic. The town is famous for its pecorino cheese, so sampling it in local shops is a must.
The streets are peaceful, and every viewpoint offers sweeping views of the Val d’Orcia. You’ll find that the town itself encourages slow travel—sit in a square, sip a glass of wine, and just watch life unfold. Pienza feels like Tuscany distilled into its purest form.
8. Cortona, Tuscany
Cortona may have gained fame from “Under the Tuscan Sun,” but it deserves its reputation. The town is perched high above the Val di Chiana and offers stunning views of the surrounding landscape.
Its streets are a mix of Etruscan history, Renaissance architecture, and modern boutiques. From my overall experience, the best way to enjoy Cortona is without a schedule—wander, stop for lunch at a local trattoria, and soak in the atmosphere. Every turn feels like a postcard waiting to happen.
9. Gubbio, Umbria
Gubbio is a medieval town with an almost storybook charm. It’s known for its Gothic architecture, historic festivals, and the beautiful Piazza Grande. The town is built on a hillside, so be prepared for some uphill walking—but the views are worth every step.
You can ride the funicular to the top of Mount Ingino for a panoramic view of the town and surrounding valleys. Gubbio also has a rich culinary scene, with hearty Umbrian dishes that feel like a warm hug on a plate. From my own personal experience, trying the local truffle dishes here is a highlight you’ll never forget.
10. Trevi, Umbria
Trevi is smaller than some of the other towns on this list, but it packs a lot of charm. Known for its olive oil, the town has narrow streets, stone houses, and beautiful views of the Umbrian hills.
Take a stroll through the old town, visit the local churches, and don’t miss a tasting at one of the olive oil mills. Trevi is peaceful and less crowded than other hill towns, making it perfect for those who want to escape the tourist trails. Based on my overall experience, sitting in the main square with a gelato and watching life go by is an experience you’ll truly savor.
Final Thoughts
Central Italy’s hill towns offer something for everyone. Whether you’re an art lover, foodie, history buff, or just someone who wants to soak in breathtaking views, these towns deliver. From wandering medieval streets to tasting local delicacies, each town provides a unique window into Italy’s past and present.
If there’s one thing I’ve learned from my own personal experience, it’s that exploring these hill towns isn’t just sightseeing—it’s slowing down, savoring every moment, and letting Italy’s charm seep into you. These towns are waiting for you, and each one promises memories that will last a lifetime.
I’m Gemma, a passionate lifestyle blogger sharing my creative world with you. Gemitaliano.com is my little corner of the internet, glad you’re here.