The beautiful village of Montalcino, located on the western slope of Val d'Orcia, is the perfect medieval destination for wine lovers. You’ve likely heard of Brunello di Montalcino, the Tuscan red wine with a woody and intense flavor that is beloved in Italy and abroad. In this guide, we’ll present an itinerary to help you explore the flavors and colors of magnificent Montalcino, offering historic sights and breathtaking views.



Wandering Through the Historic Center

Start your visit in the historic center, where you can stroll along streets and tunnels dating back to the 16th century. Here, the village has remained almost unchanged, allowing your imagination to travel back in time while the smell of wine and the charm of local shops lead you to the fortified walls of the Fortress of Montalcino. This medieval fortress, once Etruscan and later Roman, was surrounded by strong walls that made it impenetrable despite numerous sieges. Today, the Fortress of Montalcino hosts jazz or dance performances and serves as a wine-tasting venue. For a stunning view of Val d'Orcia, climb the towers of the fortress and admire the hills dotted with vineyards.

Montalcino Cathedral

After visiting the fortress and enjoying wine at Enoteca la Fortezza, continue to the Cathedral of the Holy Savior, or Montalcino Cathedral. Built on the site of a Romanesque parish church and elevated to cathedral status by Pius II in 1462, it features a simple and clean exterior typical of the neoclassical period, giving it a luminous and elegant appearance. Inside, you’ll find artistic treasures from various eras, including The Immaculate Conception with Jesus and God the Father (1588) and Saint John the Baptist in the Desert, both by Francesco Vanni. The neoclassical architecture, with its clean lines, directs visitors' attention to the altar, welcoming them with soft curves and subdued colors.

Streets of Montalcino's Historic Center

Pieri Palace and the Civic and Diocesan Museum

Pieri Palace is another must-see destination in Val D'Orcia. This magical and tranquil site will transport you to the period of French occupation in Montalcino, when soldiers were sheltered here before battles. Its shaded courtyard provides a perfect resting spot during your journey through Montalcino, offering a charming view of a medieval well at its center.

After refreshing both body and mind, proceed to the Civic and Diocesan Museum, an essential stop for art lovers. Here, you’ll admire masterpieces from the Middle Ages to the 20th century, including paintings by renowned artists of the Sienese school of the 1400s and 1500s, as well as sculptures that evoke deep emotions and fill your eyes with beauty. If you have more time in Montalcino, don’t miss the Theater of the Astrusi, a true architectural gem with romantic charm.

Before leaving, be sure to visit one of the many wineries scattered throughout the town. Treat your palate to the fantastic Brunello di Montalcino, perhaps paired with some local specialties. Our article includes a selection of the best wineries where you can enjoy an unforgettable experience amidst Tuscan vineyards! Visit the Enjoy Montalcino website to learn more about this invaluable gem of a village.