Radda in Chianti is one of the most iconic villages in the Chianti region, serving as an excellent starting point for exploring the area on foot with your dog. There are numerous trails in the area surrounding the historic center that lead you to discover woods, vineyards and dirt roads.
Among these is the Vallimaggio Trail, starting at the Convent of Santa Maria al Prato then meandering through the valley of the Rigo Stream, passing poplars, alders and vineyards. The walk alternates between scenic stretches and shaded areas, allowing you to proceed at a leisurely pace.
In Pievasciata, in the municipality of Castelnuovo Berardenga, the Chianti Sculpture Park offers a unique outdoor experience combining contemporary art and nature. The works, created by artists from around the world, are harmoniously integrated into a forest of oak and holm oak trees, reachable via a ring route surrounded by greenery.
This exploration follows an easy and pleasant route, particularly well-suited for those who want to take a walk with their dog. Pets are allowed so long as they are kept on a leash, accompanying visitors as they explore the many installations that interact with the surrounding landscape. The area includes shaded spots that are ideal for taking a break, making the Chianti Sculpture Park a perfect stop for those who want to enjoy a mix of nature, art and outdoor activities with their pets.
Near Badia a Passignano, in the municipality of Barberino Tavarnelle, the Passignano Loop offers the chance to be immersed in the most authentic Chianti landscape with your pooch. The route winds through dirt roads, woods and vineyards, partly following the ancient Strada del Guardingo di Passignano, which once connected the Val di Greve with the Val di Pesa.
The route winds through a landscape rich in scenic views and historical landmarks, alternating between shaded stretches—ideal for a brief rest—and picturesque vistas of the Chianti countryside. Along the way, you can visit the Cappella dei Pesci, a small chapel linked to the tradition of Saint Giovanni Gualberto, and pass by Casa Pugliano, the birthplace of painter Domenico Cresti, known as “Il Passignano”. An ideal walk for those who want to explore the area at a leisurely pace, surrounded by nature, history and timeless landscapes.