Siena is a real city with a medieval soul. San Gimignano is a medieval village with a tourist problem.
Plan your trip →52,000 people, university, contrade neighborhoods, Palio. Piazza del Campo. The Duomo. Hours of content. Stay overnight: the town transforms after 4pm when day-trippers leave.
7,700 people. 14 towers. World-champion gelato. Beautiful but overwhelmed 10am–4pm in summer. 2–3 hours is enough.
Siena: overnight stay, deeper exploration. San Gimignano: half-day trip from Siena or Florence.