I always recommend seeing Siena first, in the morning there are usually fewer people, so you can see it easily. If you arrive early you can also find a place in the Santa Caterina car park, the one closest to the Duomo and the city center.
Lose yourself in the narrow streets that tell you the history of the city and admire Piazza del Campo, a quick lunch if you feel like it in a restaurant in the city or stop in Monteriggioni, a medieval jewel halfway between Siena and San Gimignano, 20 minutes by car and reach San Gimignano, with its towers that remain from the past when each palace had one … this was how the lords of the time indicated wealth, the richer one was, the higher the tower was. It is mandatory to eat ice cream in the best ice cream parlor in Italy, you can find it in the main square. Another obligatory stop in a cellar, to bring home a case of “Vernaccia”, a white wine that is produced only in that area. Siena is 1 hour and 30 minutes by car from our structure.