Nestled among the rolling hills of Tuscany’s Val D’Orcia, Montalcino feels more like something out of a fairy tale or movie set than a real city. From its dreamy cobbled streets and terracotta roofs to the world-famous wineries beneath them, a visit to Montalcino is a must for any Tuscan traveler. Montalcino’s name is derived from the Latin mons ilcinus or “mountain of holm-oak,” a reference to both the city’s hilltop location and to the holm-oak, a tall and vibrant tree species found in the rolling landscapes north of the Mediterranean. 

History

Montalcino’s hilltop was first inhabited by monks and small religious settlements more than a millennium ago, but it owes its true beginnings as a city to a stroke of good luck. When a 10th-century invasion by the Saracens left neighboring cities in ruins, Montalcino was spared, leaving the city intact and ready to welcome refugees. Most of this influx came from the nearby Rusellae, a formerly prosperous city that was never rebuilt (the small, similarly-named village of Roselle now exists near its ruins). Rusellae’s contribution to Montalcino's sudden boom in population had a transformational effect on the city, sparking its development into a bastion of Tuscan culture and history.

Montalcino’s economy thrived on the export of fine leather goods along the Via Francigena, a primary trading road between France and Rome. Though Montalcino did succumb to a 12th-century takeover by the powerful Sienese Republic (the namesake of modern-day Siena), the Republic’s resources allowed the city to build walls and fortresses that remain virtually unchanged today. Even when the Sienese Republic later fell to invaders from Florence, Montalcino was able to hold out for four years in the face of aggression and repeated sieges. Ultimately absorbed by Florence after years of war in the region, Montalcino entered a period of peace and stability. Despite this turbulent history, the people of Montalcino herald their city’s history of resistance as a cornerstone of their cultural identity.

The Rise of Brunello di Montalcino

Even in a time of peace, not all was perfect in Montalcino. Its economy entered a lengthy period of decline and stagnation until a sudden turnaround in the 1860s with the unification of modern-day Italy. The reason for the city’s new trajectory? 

Montalcino’s most famous export—wine.  

Montalcino had produced wine for centuries, but periods of warfare hindered growth and innovation. In this period of newfound stability, local farmers began to experiment with the Sangiovese grape, locally known as the Brunello. One result of this experimentation was the now world-renowned wine, the Brunello di Montalcino.

However, the city was once again devastated by World War I and II as farmers were sent to war and their lands were subsequently neglected. As a primarily agricultural city, Montalcino faced more hardship from the wars than did other cities. It took until the 1980s for the economy to recover and resume large-scale wine production. This growth was only boosted when Brunello di Montalcino was awarded DOCG status, the highest classification of Italian wines. With Brunello di Montalcino’s place solidified among the upper echelons of fine red wines, it almost singlehandedly transformed Montalcino from one of Italy’s poorest towns into a prosperous one, having repeatedly pulled the local economy from near ruin. Today, Montalcino is a can’t-miss destination for travelers hoping to try these famed wines for themselves and experience the city’s rich history. 

Experiencing Montalcino 

To visit Montalcino is to experience living history. The city’s architecture has remained virtually unchanged since the 16th century, and numerous historic buildings, works of art, and artifacts can be found around every corner. On our Tuscany Wellness Tours, we have the opportunity to take in Montalcino’s history and culture firsthand with the help of local guides. From walking the city’s ancient stone footpaths to gazing out at the lush vistas of the surrounding Val D’orcia, this city’s vibrant culture and landscape are sure to leave guests captivated. And since our travel philosophy encourages guests to slow down, enjoy the present moment, and embrace the natural beauty of our surroundings, Montalcino makes the perfect destination. 

Our Tuscany Wellness Retreats provide ample opportunity to appreciate the historical landmarks and natural splendor of Montalcino, but we also dive into the town’s famous wine culture. At Argiano—one of Montalcino’s most notable wineries—tastings are accompanied by an exclusive private tour of its historic estate. Argiano is a living testament to the region’s dramatic history, located on a gorgeous property that has been home to countless noble families, changing hands as each rose and fell from power. We discover the estate at the side of the current proprietors, and our wine tasting is complemented with a freshly prepared meal specially arranged for our groups.

Interested in exploring Tuscany the right way? Join us on our Tuscany Wellness Adventure! Our itineraries seamlessly blend cultural immersion, active exploration, and daily wellness opportunities to provide you with an authentic, rich travel experience.

For more information, download our trip details or email us at info@terraandtu.com