From Pienza to Volterra, from Pitigliano to San Gimignano, here are tips for
visiting some of Tuscany’s most iconic
places, alternating walks through the historic centers with stops in the green
spaces that often surround these ancient towns.
Overlooking the landscapes of the Val d’Orcia, Pienza is one of Tuscany’s most famous villages. Its elegant Renaissance streets and picturesque squares can be easily explored on foot with your dog, as you stroll past iconic landmarks such as Piazza Pio II, the Duomo and the charming alleys of the historic center, including Via del Bacio and Via dell’Amore.
With every step, stunning views of the surrounding hills unfold. Particularly enjoyable is the route along the walkway that runs along the outside of the historic walls, from which you can admire some of the most iconic views of the Val d’Orcia. With its many scenic views and open spaces, Pienza is an ideal destination to explore at a leisurely pace, letting yourself be guided by the beauty of the area.
Volterra preserves a heritage that spans centuries of history, from Etruscan artifacts to the Middle Ages. As you stroll with your pet along the streets of the historic center, you’ll come across iconic landmarks such as Piazza dei Priori, the heart of the city, the picturesque Porta all’Arco and sections of the ancient Etruscan walls, which still tell the story of the town’s millennia-old history. There is no shortage of stunning views of the rolling hills surrounding Volterra, among the most picturesque in Tuscany.
At the foot of the Medici Fortress—which is currently closed to visitors—the Enrico Fiumi Archaeological Park offers a pleasant green space where you can stroll and relax in the shade. For those who wish to continue exploring nature, the trails winding through the city’s surrounds and the natural areas of the region, such as the Berignone Forest Nature Reserve, offer the chance to alternate village visits with scenic strolls through the hills, woods and landscapes typical of the Tuscan hinterland.
Perched on a spectacular tuff outcrop, Pitigliano offers one of the most breathtaking views in Tuscany. The historic center is a maze of narrow streets, quaint piazzas and remnants of a history stretching back 1000 years. Among the town’s most iconic landmarks are the imposing Medici Aqueduct that defines the town’s skyline and the ancient Jewish Ghetto, a testament to a community that helped make Pitigliano an important cultural center of the Maremma.
The area surrounding the village is also home to the famous Vie Cave, ancient paths carved into the tuff by the Etruscans that today allow you to explore the area with your dog, immersed in a cool, shaded natural setting.
With its unmistakable profile emerging among the hills, San Gimignano is one of the most iconic places in Tuscany. While walking with your pet through the streets of the historic center, you can visit iconic sites such as Piazza della Cisterna, the heart of city life, and Piazza del Duomo, dominated by historic buildings that tell the story of the town’s long history.
Among the attractions open to visitors accompanied by their dogs is the Museum of Torture, one of the city’s most unique cultural sites. For a break in the great outdoors, you can visit the Rocca di Montestaffoli, a large, scenic green space offering stunning views of the Val d’Elsa hills and serving as an ideal destination for a walk or some relaxation with your pet.
In the area surrounding the historic center, trails and side roads dip into vineyards, olive groves and rolling hills, offering further opportunities to explore the landscape surrounding one of Tuscany’s most famous villages.