Begin your journey along Via di Gracciano nel Corso, a lively and elegant street lined with medieval buildings, like Palazzo Bucelli and the ancient Porta al Prato. With boutique shops, artisanal stores, and historic façades, it’s the perfect place for window shopping, people-watching, and soaking in the village’s timeless charm.

Continue to the Marzocco Monument, a majestic lion sculpture once symbolizing Florence’s power. Snap iconic souvenir photos here and learn about Montepulciano’s historic ties with the Florentine Republic during the Renaissance.

Then, pass by Avignonesi Palace, a true architectural gem by Giacomo da Vignola. Its elegant proportions and refined late-Renaissance style stand as a testament to the artistic grandeur of the 16th century.

Make your way to Belvedere di Voltaia, a scenic viewpoint offering sweeping vistas of Montepulciano’s rooftops and the rolling Tuscan countryside beyond. It’s one of the best spots to take in the romantic skyline and the serenity of the hills.

Next, step into Piazza Grande, the beating heart of Montepulciano. With vibrant events like the Bruscello Poliziano during Italy’s traditional holiday of Ferragosto, bustling open-air markets, and inviting cafes, the square is always full of life. Pause to admire the stone sculptures of griffins and lions—a nod to the town’s rich iconography.

From there, explore the iconic landmarks flanking the square. Visit the 16th-century Cathedral of Saint Mary of the Assumption, built in the Florentine tradition with its austere plaster surfaces and balanced forms. Then, admire the Town Hall, dating back to the 14th century, whose battlemented tower echoes Florence’s Palazzo Vecchio and has silently witnessed centuries of civic life and historic events.

End your tour at the remarkable Cantine Storiche De’ Ricci, often called the “Cathedral of Wine.” Descend into vast underground cellars carved from volcanic tufa stone, supported by soaring Gothic-Renaissance vaults and sturdy pillars. Here, you can taste Montepulciano’s finest wines and local specialties while exploring one of the most atmospheric and storied wine cellars in all of Tuscany at your own pace.