Tuscany Walking and Wine

This eight-day tour by Explore Worldwide traces a route from Pisa to Florence, focusing on gentle walks along the famous 'strade bianchi'—the white gravel roads of Tuscany. Starting outside San Gimignano, the hike follows part of the ancient Via Francigena past vineyards and rural homes, with views of the town’s medieval towers before a wine tasting at a family-run cellar.

Further on, the itinerary calls for walks through the Chianti Hills, exploring Castellina and its local wineries, before heading south to Siena’s grand Gothic architecture. After a stop in Pienza with its Renaissance feel and a cheese tasting, the walk continues through the Val d’Orcia to Montalcino and its celebrated Brunello wine. The tour finishes with time to wander Florence’s Renaissance streets, including the Ponte Vecchio and the Piazzale Michelangelo viewpoint.

Along the way, the pace allows for plenty of pauses to enjoy local flavours and soak up daily life; returning to hotels with gardens or historic settings rather than rushing on. This isn’t about miles covered but about a measured passage through a region shaped by history, agriculture and hills.

New to Italy? Our Italy guide has the practical essentials: money, plugs, visas and when to go.

These are the places the trip visits, in order. Explore Worldwide publishes the day-by-day itinerary on its own site.