Five minutes above the Oltrarno the city simply stops, and this climb from the southern gate up to Galileo's last house is the cleanest way to feel it happen — pavement to cypress, traffic to birdsong, in a single steady rise. Do it in the morning, before the sun sits on the unshaded lane.
Start at Porta Romana, the brick gate of 1328 that survived when the walls came down, and look back at the worn fresco in the arch. Then up Via di Annalena, named for the widow who made her house a convent, where the gradient is still kind. The Bobolino below Boboli's edge gives the first view back — the dome floating over the roofs — before Via di San Leonardo turns properly rural, all walled olive terraces and the cypresses Tchaikovsky once lodged among.
The lane lifts you to Pian dei Giullari, the ridge hamlet of stone-walled villas, and to Villa Il Gioiello — where Galileo lived out his house arrest after 1633, going blind under a sky he was forbidden to name. The house is usually shut; the view and the cypress lane are the point. Turn here; the descent is easy.
