Italy’s history is unmatched, leaving behind examples of its vast legacy, such as the Colosseum in Rome, a symbol of the Roman Empire’s engineering brilliance, and Florence’s Palazzo Pitti, a hallmark of Renaissance grandeur. Medieval heritage thrives in landmarks like Castel del Monte in Puglia, which showcases centuries of architectural and cultural milestones.
Also, the hills of Italy, stretching across regions like Tuscany, Umbria, and Lazio, have shaped the country’s identity. These rolling landscapes are blanketed with vineyards, olive groves, and dense forests. They provide the perfect backdrop for centuries-old settlements. Many of these hills are crowned with fortified towns, originally built for protection but now celebrated for their beauty and history.
For those who appreciate both scenic vistas and historic sites, Italy’s hill towns are captivating destinations. Their ancient streets, preserved traditions, and iconic landmarks offer visitors a chance to connect with Italy’s storied past. Here are ten must-visit historic hill towns in Italy.
1. San Gimignano, Tuscany
San Gimignano, a captivating hill town in Tuscany, Italy, stands proudly atop a 324-meter hill overlooking the picturesque Elsa Valley. Its history dates back to the 3rd century BC when it began as an Etruscan settlement. Named after Saint Geminianus, who is believed to have saved the town from invaders in the 10th century AD, San Gimignano flourished during the Middle Ages as an essential stop along the Via Francigena, the pilgrimage route to Rome.
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Known as the “Town of Fine Towers,” its skyline was once dotted with 72 soaring structures built by noble families vying for prestige. Today, 14 of these towers remain, preserving the town’s distinctive medieval character. You will be drawn to its cobbled streets and landmarks, including the Romanesque Collegiate Church adorned with frescoes and the Torre Grossa, the tallest tower offering sweeping views of the countryside.
2. Civita di Bagnoregio, Lazio
Often referred to as “La città che muore” or “The Dying City,” Civita di Bagnoregio is a remarkable hilltop village in Italy’s Lazio region. Founded by the Etruscans over 2,500 years ago, it has endured centuries of natural erosion and seismic activity, which have gradually isolated it from neighboring areas.
Perched atop a fragile tuff hill, Civita di Bagnoregio is accessible only via a pedestrian bridge. The village’s medieval architecture, narrow alleys, and flower-adorned balconies exude a timeless charm. Notable sites include the Church of San Donato, dating back to the 5th century, and the Porta Santa Maria, an ancient gateway carved by the Etruscans.
Despite its precarious position, efforts have been made to preserve Civita’s unique heritage. In 2013, a toll was introduced for visitors crossing the footbridge, with proceeds dedicated to conservation.
3. Volterra, Tuscany
Established by the Etruscans as Velathri, Volterra was among the twelve cities of the Etruscan League. Today, you can explore remnants of its storied past, including the well-preserved Porta all’Arco, a monumental gate from the 4th century BC.
The town’s rich heritage is showcased in the Guarnacci Etruscan Museum, one of Europe’s oldest public museums, housing an extensive collection of Etruscan artifacts. Among its treasures is the “Shadow of the Evening,” a slender bronze figure that captivates with its elongated form.
Volterra’s medieval charm is evident in landmarks like the Palazzo dei Priori, Tuscany’s oldest town hall, and the imposing Medici Fortress, which, intriguingly, now functions as a prison.
The town is also renowned for its alabaster craftsmanship, with artisans creating exquisite pieces from this translucent stone, a tradition that has earned Volterra the nickname “City of Alabaster.”
Cultural events enliven Volterra throughout the year. Notably, the Volterra AD 1398 festival in August transports visitors back to medieval times with reenactments, markets, and performances. Additionally, the town’s picturesque streets and panoramic vistas have made it a favored location for filmmakers.
4. Montepulciano, Tuscany
Montepulciano, a medieval and Renaissance hill town in southern Tuscany, is perched atop a 605-meter limestone ridge, where it offers commanding views of the surrounding Val d’Orcia and Val di Chiana valleys. According to tradition, Montepulciano was founded by the Etruscan King Porsenna in the 6th century BC.
The town’s strategic location made it a coveted prize during the medieval power struggles between Florence and Siena.
The town is also famous for its wine, particularly Vino Nobile di Montepulciano, a red wine made primarily from Sangiovese grapes. You will be happy to see the town’s historic center, which is full of elegant Renaissance palaces, ancient churches, charming squares, and hidden corners.
5. Assisi, Umbria
Nestled on the western slopes of Monte Subasio in Umbria, Assisi is renowned as the birthplace of St. Francis, the founder of the Franciscan Order in 1208.
A visit to Assisi is incomplete without exploring the Basilica of San Francesco d’Assisi, a UNESCO World Heritage Site. This awe-inspiring structure consists of two churches, the Upper and Lower Basilicas, both adorned with frescoes by masters like Giotto and Cimabue. Beneath the Lower Basilica lies the crypt where St. Francis is interred.
Another significant site is the Basilica of Santa Chiara, dedicated to St. Clare, a follower of St. Francis and founder of the Poor Clares. This Gothic church houses her remains and the famous Cross of San Damiano. The Romanesque Cathedral of San Rufino, where both St. Francis and St. Clare were baptized, stands as a testament to Assisi’s deep spiritual roots.
For a glimpse into the town’s ancient past, the Temple of Minerva, now the Church of Santa Maria sopra Minerva, reveals its Roman origins.
Meanwhile, the medieval Rocca Maggiore fortress offers breathtaking views of the Umbrian valley and insights into Assisi’s strategic importance during the Middle Ages.
Assisi’s cultural heritage is further highlighted by the annual Calendimaggio Festival, a vibrant celebration held in early May that reenacts medieval and Renaissance life through processions, theatrical presentations, and traditional contests.
6. Orvieto, Umbria
Orvieto, perched atop a volcanic tuff cliff in Umbria, is a town rich in history and architectural marvels. Its origins trace back to the Etruscans, with remnants like the Crocifisso del Tufo necropolis, a testament to its ancient past.
The town’s skyline is dominated by the Orvieto Cathedral, a masterpiece of Italian Gothic architecture. Initiated in 1290, the cathedral boasts a façade adorned with intricate bas-reliefs and golden mosaics, while its interior houses frescoes by Luca Signorelli.
Beneath the surface, Orvieto reveals a labyrinth of underground tunnels and caves carved from the soft volcanic rock over millennia. These subterranean passages, once used for various purposes, including as bomb shelters during World War II, offer a fascinating glimpse into the town’s multifaceted history.
A remarkable feat of engineering is the Pozzo di San Patrizio or St. Patrick’s Well. Constructed between 1527 and 1537, this 53-meter-deep well features a double helix staircase, allowing for efficient access to water during times of siege.
The medieval Torre del Moro stands as a sentinel in the town’s center. Climbing its 47 meters rewards visitors with panoramic views of Orvieto and the surrounding Umbrian countryside.
7. Cortona, Tuscany
Cortona’s origins trace back to the Etruscan civilization, evident from the ancient city walls dating to the 5th century BC and the renowned Tabula Cortonensis, one of the longest Etruscan inscriptions ever discovered.
Art and history lovers will be thrilled by the Museo dell’Accademia Etrusca, which houses extraordinary relics, including an ornate bronze Etruscan chandelier and the famous Tabula Cortonensis, an inscription that unlocks pieces of Italy’s ancient past. Just a few steps away, the Diocesan Museum dazzles with Fra Angelico’s ethereal Annunciation, a painting so luminous it feels as if it were blessed by Tuscany’s golden light.
Spiritual seekers find solace in the Basilica of Santa Margherita, standing proud at the town’s highest point. Its serene interior, dedicated to Cortona’s patron saint, rewards both pilgrims and curious wanderers. The Church of San Francesco, modest yet magnetic, quietly guards relics of St. Francis of Assisi, offering a soulful pause.
Winding cobbled streets, lined with rustic trattorias and artisan boutiques, lead to views that will stop you in your tracks: a sweeping vista of olive groves, vineyards, and the shimmering blue of Lake Trasimeno in the distance. Every turn feels like a reward, every step an invitation to linger.
For those lucky enough to visit during the “Cortona On The Move” festival, the town buzzes with creativity as photography transforms ancient piazzas into vibrant canvases.
8. Montalcino, Tuscany
Montalcino, a picturesque hilltop town in Tuscany, is renowned for its medieval charm and exceptional wine production. Dominating the town’s skyline is the 14th-century fortress, La Fortezza di Montalcino, which offers panoramic views of the surrounding Val d’Orcia countryside. Visitors can explore its ancient walls and even enjoy wine tastings within its historic enoteca.
You will enjoy visiting historic landmarks such as the Palazzo dei Priori, located in the central Piazza del Popolo. Dating back to the late 13th century, this building showcases the coats of arms of past rulers and features a medieval tower with battlements and a clock.
Montalcino is perhaps best known for its production of Brunello di Montalcino, one of Italy’s most prestigious wines. Wine enthusiasts can visit numerous local wineries to sample this renowned red wine, made exclusively from Sangiovese grapes.
Just outside the town lies the Abbey of Sant’Antimo, a stunning Romanesque church believed to date back to the 8th century. Surrounded by olive groves and vineyards, the abbey provides a serene retreat and a glimpse into the region’s spiritual heritage.
9. Todi, Umbria
This Italian hill town’s origins date back to the Etruscan era, with the town’s layout reflecting its ancient roots. The central Piazza del Popolo, one of Italy’s most picturesque squares, is surrounded by medieval and Renaissance architecture, including the Palazzo del Popolo and the Palazzo del Capitano. These historic buildings stand as testaments to Todi’s rich past.
If you want to explore the religious heritage of Todi, you’ll be happy to visit the Cathedral of Santa Maria Annunziata, a Romanesque Gothic structure that houses impressive artwork.
The town is also renowned for its vibrant cultural scene, hosting events such as the Todi Festival, which celebrates performing arts and attracts visitors from around the world. Additionally, the surrounding Umbrian countryside, with its rolling hills and vineyards, provides a serene backdrop for those seeking a tranquil escape.
Exploring Todi’s narrow streets, you can discover artisan shops, traditional trattorias, and panoramic viewpoints that offer breathtaking vistas of the Tiber Valley.
10. Pitigliano, Tuscany
Pitigliano, often referred to as “Little Jerusalem,” is a captivating town in southern Tuscany. Perched atop a dramatic tuff cliff, the town’s origins trace back to the Etruscan era, with ancient cave dwellings and necropolises carved into the volcanic rock.
If you want to explore the town’s medieval and Renaissance architecture, then you need to head to the Orsini Fortress. Additionally, the 16th-century aqueduct, with its series of arches, showcases the engineering prowess of the era.
Pitigliano’s rich Jewish heritage is a significant aspect of its identity. In the 16th century, it became a refuge for Jews fleeing persecution, leading to the establishment of a thriving Jewish community. The Synagogue, built in 1598, stands as a symbol of this enduring legacy. Visitors can explore the Jewish Quarter, which includes the Synagogue, a ritual bath (mikveh), and the kosher butcher.
The town is also known for its distinctive white wine, Bianco di Pitigliano, which has been produced in the region for centuries. This crisp and refreshing wine is made primarily from Trebbiano Toscano grapes, reflecting the area’s viticultural traditions.
While exploring Pitigliano’s narrow alleys, you’ll discover artisan workshops, traditional trattorias, and panoramic viewpoints offering breathtaking vistas of the surrounding Tuscan landscape.
