Between Florence and Siena, this is not a short transfer; it is Chianti work. The route climbs out of the Arno basin south of the city, past villas, walls and olive slopes. After San Casciano, the riding turns rural: vineyards, cypress trees, short descents and the next ramp waiting immediately. Around Badia a Passignano and Castellina in Chianti, the day collects most of its elevation, with open views across vines and woodland. The final kilometres roll over the hills into Siena, where red brick and narrow streets make the finish unmistakable.