Top 5 Small Towns in Toscana, Italy with Big Character

Discover Toscana’s Hidden Gems: Top 5 Small Towns with Big Character

Top 5 Small Towns in Toscana, Italy with Big Character

Montalcino

Nestled on a hilltop, Montalcino offers sweeping views and is famously known for producing the world-renowned Brunello wine. Wander through its medieval streets, sample the local vintages, and feel the charm that fills every corner. Accommodation options are abundant, explore them on Search and Stay.

Montepulciano

Montepulciano delights visitors with its Renaissance architecture and vibrant piazzas. Dive into the rich wine culture by visiting the underground cellars or enjoy a pasta-making class. For a perfect stay, check accommodations at Accessibility Stays or Stays with Pools.

San Gimignano

Famed for its medieval towers, San Gimignano is a step back in time. Wander through cobbled streets lined with artisanal shops and relax with a gelato in Piazza della Cisterna. For a memorable stay, consider booking with Bike, Hike and Ski.

Pienza

Known as the “Ideal City” of the Renaissance, Pienza offers picture-perfect streets and unbeatable Pecorino cheese. It’s the ideal place to learn about history and enjoy local flavors. Find ideal accommodation at On the Farm Stays.

Cortona

With its famous views and artistic history, Cortona is a lively town filled with wonderful experiences and memories to be made. From hillside hikes to street-side cafes, you’ll leave enchanted. Accommodations are available on Pack your Pet or Stays By Me.