For most travelers in 2026, a stay of 4 to 6 hours is sufficient to see the highlights of San Gimignano, making it a perfect day-trip destination from Florence or Siena. Within this timeframe, you can walk the medieval cobblestone streets, climb the Torre Grossa (the tallest of the remaining 14 towers) for breathtaking views of the Tuscan countryside, and visit the stunning frescoes inside the Collegiata. You will also have ample time to wait in the (inevitable) line for world-award-winning gelato at Gelateria Dondoli in Piazza della Cisterna. However, if you are a lover of photography or want to experience the town without the heavy tour-bus crowds, staying overnight is highly recommended. Once the day-trippers depart after 5:00 PM, the "Manhattan of the Middle Ages" transforms into a serene, romantic village where you can enjoy a quiet glass of local Vernaccia wine. A full 24-hour stay allows you to explore the perimeter walls and the fortress of Montestaffoli at a more relaxed, authentic pace.