15 Picturesque Medieval Towns in Italy That Will Capture Your Heart

Stepping into Italy’s medieval towns is like walking straight into the pages of a storybook. These picturesque locations are brimming with ancient history, stunning architecture, and enchanting landscapes.

For travel photographers, these towns offer unparalleled opportunities. You can capture narrow cobblestone streets and centuries-old castles to sweeping views of rolling hills and hidden courtyards.

Beautiful Medieval Italian Towns

1. Civita di Bagnoregio, Viterbo

Perched atop a dramatic hill, Civita di Bagnoregio is known as “the dying town” because of its eroding foundation. Accessible only by a pedestrian bridge, this tiny village in the Lazio region feels suspended in time. Picturesque narrow streets wind between centuries-old stone houses.

The best view of the village is from the base of the pedestrian bridge—especially at sunrise or sunset when the warm light accentuates the town’s ethereal beauty.

2. Montagnana, Padova

Surrounded by some of the best-preserved medieval walls in Europe, Montagnana is a fortress of untouched charm. This gem boasts 24 imposing towers and four gates that date back to the 14th century. Its streets are a wonder of traditional Italian architecture, with lively piazzas and charming trattorias.

Montagnana’s walls are a must-see. Capture wide shots of the formidable walls or zoom in on the intricate brickwork. The town also hosts the annual Palio di Montagnana, a medieval horse race packed with color and pageantry that’s perfect for action photography.

3. San Gimignano, Siena

San Gimignano, often called the “Town of Fine Towers,” is the pinnacle of medieval architecture in Tuscany. Out of the original 72 towers, 14 remain, creating a stunning skyline that dominates the rolling Tuscan countryside. Piazza della Cisterna, with its central well and surrounding medieval buildings, is a fantastic spot to capture the town’s character.

Photographers will fall in love with sweeping panoramas from Torre Grossa, the tallest tower in town. Don’t miss the opportunity to wander San Gimignano’s vineyards for scenic compositions of the countryside and the town in the background.

4. Bologna, Bologna

Known as the “Red City” for its terracotta-colored buildings and porticoes, Bologna seamlessly blends medieval charm with modern sophistication. The highlight is Piazza Maggiore, featuring historic structures like Basilica di San Petronio. The two towering symbols of the city, Le Due Torri (The Two Towers), dominate the skyline and make for dramatic subjects.

For photographers, Bologna’s endless porticoes are a dream. Whether it’s the warm tones of the morning light spilling through or the picturesque arches creating natural leading lines, the opportunities are endless. Urban photographers will love capturing daily life here—Bologna bustles with vibrant energy.

5. Pitigliano, Grosseto

Pitigliano, carved into the volcanic tuff of southern Tuscany, is often called the “Little Jerusalem” for its rich Jewish heritage. This unique town appears to be growing out of the rugged cliffs, with its rooftops blending seamlessly into their natural surroundings.

The aqueduct and the Collegiate Church of San Pietro are key spots for framed shots. A stroll along the pathways surrounding the town’s base offers jaw-dropping angles of Pitigliano towering dramatically above.

6. Montepulciano, Siena

Famed for its world-class wine, Montepulciano pairs rolling vineyard views with a medieval urban aesthetic. The Piazza Grande, lined with dignified Renaissance-era buildings and crowned by the Palazzo Comunale, serves as the heart of this hilltop town.

Photographers will appreciate the balance of nature and history here. Shots of the Tuscan countryside framed by Montepulciano’s rustic streets are postcard-perfect. Don’t forget to venture up the Palazzo Comunale’s bell tower—it offers extraordinary panoramic views.

7. Urbino, Pesaro

In the Marche region, Urbino’s Renaissance character makes it a standout location. Its star feature is the majestic Palazzo Ducale, a UNESCO World Heritage Site with twin turrets that rise above the landscape.

Urbino offers endless photographic possibilities. Golden light makes the well-preserved bricks glow, and the town’s hilly streets provide interesting perspectives. You can also frame the town’s façade against the surrounding green hills.

8. Matera, Matera

Once abandoned but now celebrated, Matera is one of the most evocative towns in southern Italy. Its ancient cave dwellings, known as Sassi, make this a cultural treasure. Wandering Matera’s maze-like alleys feels like stepping back thousands of years.

Evening and night offer magical moments for photographers. The cave houses lit against the darkening sky create a mesmerizing glow perfect for low-light and long-exposure shots.

9. Atrani, Salerno

Tucked into a sheer cliffside on the Amalfi Coast, Atrani is a tiny town but brims with Mediterranean allure. The Church of San Salvatore and the picturesque piazzas are excellent focal points for photographers.

The stunning coastal setting sets Atrani apart, especially during sunset hours. Capture the town’s charming architecture with the sea as a backdrop, and experiment with perspective by shooting from above along the walking trails.

10. Ostuni, Brindisi

Dubbed the “White City,” Ostuni’s dazzling whitewashed buildings sparkle under the sun. This hilltop town boasts mesmerizing alleys, vibrant doorways, and terraces with views of olive groves stretching to the sea.

Photographers will appreciate the striking contrast of Ostuni’s bright white walls against the clear blue sky. Every corner of the labyrinthine old town is a picture-perfect scene.

11. Assisi, Perugia

Assisi, renowned for its spiritual heritage, is nestled in the green heart of Umbria. The town is famously associated with St. Francis of Assisi and features historic religious landmarks such as the grand Basilica of San Francesco.

Photographers flock here to capture its dramatic hilltop setting and spiritual ambiance. Sunrise casts a serene light over the Basilica and the surrounding valley, making for ethereal photos. The peaceful cobblestone streets, adorned with flowers and ancient stone structures, offer endless opportunities to explore intimate compositions that highlight Assisi’s timeless charm.

12. Orvieto, Terni

Perched atop a dramatic cliff, Orvieto commands breathtaking views of the Umbrian countryside. The town is best known for its magnificent Duomo, a masterpiece of Italian Gothic architecture with its intricate façade adorned with bas-reliefs and golden mosaics.

Orvieto’s streets are home to historic architecture and vibrant local life. Narrow cobblestone alleys wind through the town, leading to charming piazzas bustling with cafes and artisan shops. Hilltop vantage points deliver sweeping vistas of rolling vineyards and olive groves, punctuated by the silhouette of the town’s majestic towers and the imposing bulk of the cathedral.

13. Stilo, Reggio Calabria

In the foothills of Mount Consolino, Stilo captures the imagination with its blend of Byzantine and medieval architecture. This small town, often overlooked by tourists, is home to the Cattolica di Stilo, a stunning 10th-century Byzantine church that boasts a unique, cross-in-square plan.

Stilo’s narrow, winding streets lead to beautifully preserved palazzi and charming homes that reflect centuries of craftsmanship. The town’s elevated position provides panoramic views of the surrounding landscape, which stretches towards the Ionian Sea.

14. Verona, Veneto

Verona, famously known as the setting of Shakespeare’s “Romeo and Juliet,” marries romantic history with vibrant culture. The city’s Roman amphitheater, the Arena di Verona, is a remarkable 1st-century construction still in use today for grand opera performances.

The Piazza delle Erbe, once a Roman forum, stands today as a lively square lined with colorful frescoed buildings and topped by the striking Torre dei Lamberti. The adjacent Piazza dei Signori offers a slightly more subdued charm with its central monument and surrounding palaces providing a quiet dignity amidst the urban hustle.

15. Civitella del Tronto, Teramo

On a hilltop overlooking the Gran Sasso massif, Civitella del Tronto is a captivating fortress town bathed in the rich history of its storied past. The centerpiece is the Bourbon Fortress, one of the largest in Europe, spreading majestically across the hill and offering panoramic vistas of the surrounding landscape.

The narrow alleys and cobblestone streets meander between elegant façades and quaint courtyards. Architectural beauty is especially evident in structures like the Church of San Francesco, with its impressive Renaissance portal and intricately designed interior.