What’s the best part of hiking in Tuscany? Lilly is certain: it’s on foot that you truly uncover the hidden trails and charming, authentic Italian towns. Along quiet paths winding through gentle hills, vineyards, and ancient olive groves, you discover the real Italy.
Even Florence, the starting point, is reason enough to choose a hiking journey through picturesque Tuscany. In its magnificent buildings, narrow streets, and lively squares of the old town, the spirit of the Medici family is still palpable today. From the vibrant city, Lilly and her partner venture into the countryside, where the full charm of the region reveals itself from the very first stage.
With the scent of pine in the air, storybook-perfect trails carry them through the world-famous Chianti wine region to Castellina in Chianti. Over the next few days, they hike from one enchanting Etruscan town to the next: Siena, San Gimignano, and Volterra. They stroll through romantic streets, explore historic sites, stay in traditional country houses, and savor a glass of Chianti at sunset overlooking the rolling vineyards—perhaps at Lilly’s personal favorite spot. The Tenuta Casenuove vineyard is just one of many places that perfectly embody the journey’s title: Picturesque Tuscany.