The Chiantigiana — Greve + Panzano

Depart villa via SS73 east then SR222 north. Take the Chiantigiana slowly — the drive is part of the experience.

Arrive Panzano in Chianti. Park on the approach road or in the small village car park (free). Walk to Via XX Luglio.

Macelleria Cecchini (free to browse): the most famous butcher shop in Italy. Browse the counter — entire Chianina cuts, lardo, finocchiona, house-made salumi, and the legendary bistecca. Cecchini himself is usually present. The atmosphere (food, music, Cecchini's recitations from Dante) is unlike any other retail experience in Italy. Allow 45 minutes minimum.

Drive north 8 km to Greve in Chianti (15 minutes).

Piazza Matteotti: the distinctive asymmetric triangular piazza enclosed by porticoed buildings, with a bronze statue of Giovanni da Verrazzano (the Florentine navigator who explored New York harbour in 1524). Saturday market fills the piazza 09:00–13:00.

Enoteca del Chianti Classico (inside Palazzo del Gallo, Piazza Matteotti): the definitive cellar of Chianti Classico DOCG production — 200+ producers, wines by the glass and bottle. The best single introduction to Chianti Classico available anywhere. Allow 45–60 minutes.

Drive south 20 km on SR222 from Greve to Castellina in Chianti (25 minutes). The road south of Greve is the most photographed section of the Chiantigiana.

Via delle Volte (free): a remarkable roofed medieval tunnel that runs beneath Castellina's town walls for 130 metres, with arched windows looking directly over the Chianti valley. Then walk the medieval main street (Via della Rocca / Via Ferruccio).

Enoteca Antiquaria Toscana (Via della Rocca) or any of several enoteca on the main street for a second Chianti Classico tasting. Optional extension: Radda in Chianti (10 km east via SP429) — a third hill town with medieval Palazzo del Podestà and good enoteca.

Depart Castellina for Cortona via SS73 south. Estimated return: 5:15 PM direct or 6:45 PM with Radda detour.