Monteriggioni + San Gimignano

Arrive Monteriggioni. Park roadside just outside Porta Franca on the south side (free). Begin with the exterior circuit: walk the perimeter of the walls (~20–30 minutes, flat grass and gravel path). 14 towers and four gates largely intact.

Enter through Porta Franca into the village. Piazza Roma with the Romanesque parish church. Optional: Monteriggioni in Arme museum (~€5) — medieval armour, weapons, and siege machinery. 30–45 minutes.

Depart Monteriggioni for San Gimignano via SP1 (~30 minutes).

Arrive San Gimignano. Park at Parcheggio Giubileo (near Porta San Giovanni, outside ZTL, ~€2/hr). Walk up through Porta San Giovanni into the town.

Piazza della Cisterna: the triangular medieval square with the 13th-century cistern well at its centre. One of Italy's most photogenic squares. Free. 15 minutes.

Collegiate Church of Santa Maria Assunta (~€4): 14th-century Old Testament cycle, New Testament cycle, Last Judgment, and Ghirlandaio's Santa Fina Chapel (1475) — a small masterpiece of Early Renaissance fresco painting. Allow 45 minutes. CLOSED MONDAYS.

Torre Grossa and Museo Civico (~€9 combined pass): climb the 54-metre tower for the finest vantage point in the town (views over the tower skyline, Val d'Elsa, Chianti hills). Lippo Memmi's Maestà (1317) in the Museo Civico below. 45 minutes.

Vernaccia di San Gimignano tasting: Enoteca Gustavo (Via San Matteo 29) for the best wine selection, or the Rocca di Montestaffoli wine museum (~€4, includes tasting). Italy's first DOCG white wine. 30 minutes.

Optional: San Gimignano 1300 museum (~€8): remarkable scale model showing all 72 original towers in the medieval town as it appeared in 1300. 25 minutes.

Gelateria Dondoli (Piazza della Cisterna 4): multi-time world gelato champion. Crema di Santa Fina (saffron, pine nuts, sweet cream) and Champelmo (grapefruit-Champagne sorbet). Non-negotiable.

Depart San Gimignano. Return to Cortona ~6:30 PM.