With scenic towns like Radda, Castellina and Castelnuovo Berardenga within its borders, it makes a perfect destination for those looking to enjoy countryside views, exceptional food and wine, and a traditional way of life. These are our top 10 small towns in the Chianti to help you organise your trip.

Chianti remains one of the most rewarding regions to visit in Italy in 2026, especially for those who appreciate "slow travel." Located between Florence and Siena, this region offers the quintessential Tuscan landscape: rolling hills, cypress-lined driveways, and endless vineyards. It is a "good" place to visit because it successfully balances world-class tourism with authentic agricultural life. In 2026, the region has leaned heavily into "Agriturismo", allowing guests to stay on working wine estates and participate in olive harvests. Towns like Greve, Castellina, and Radda in Chianti provide charming bases for exploring medieval castles and hidden wine cellars. It is ideally visited by car, as the "Chiantigiana" (SR222) road is one of the most beautiful drives in the world. Whether you are a wine connoisseur looking for the "Black Rooster" (Gallo Nero) seal of quality or simply looking for a peaceful retreat from the museum-heavy crowds of Florence, Chianti offers a sensory-rich experience that defines the heart of the Italian countryside.