Montepulciano - Private Historic Walking Tour

Wander through the storybook charm of Montepulciano, where cobbled lanes echo with history and every corner hides a gem. Stroll along Gracciano Street lined with artisan boutiques, soak up sweeping views from Voltaia Belvedere, and feel the heartbeat of the city in lively Piazza Grande. Admire Renaissance masterpieces, uncover tales of civic pride at the Town Hall, and wrap up your journey deep underground in the majestic De’ Ricci wine cellars, where the region’s winemaking heritage comes alive. This walking tour is your gateway to the spirit, scenery, and flavor of Tuscany—one timeless step at a time.

1. 1

   Via di Gracciano nel Corso

   15 min

   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.

2. 2

   Colonna Del Marzocca

   15 min

   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.

3. 3

   Avignonesi

   15 min

   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.

4. 4

   Stop 4

   15 min

   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.

5. 5

   Piazza Grande

   15 min

   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.

6. 6

   Stop 6

   15 min

   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.

7. 7

   Stop 7

   20 min

   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.

• Infants and small children can ride in a pram or stroller
• Service animals allowed
• Public transportation options are available nearby
• Not recommended for travelers with spinal injuries
• Not recommended for travelers with poor cardiovascular health
• Travelers should have at least a moderate level of physical fitness

All sales are final. No refund is available for cancellations.