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- Torre Grossa — The tallest tower you can climb in town; the stairs are worth it for the 360° views over towers, vineyards and the Tuscan hillscape, and for feeling what a medieval lookout felt like.
- Palazzo Comunale (Civic Museum) — Right next to the Duomo, the palace holds civic frescoes, a small pinacoteca and period rooms that tell the city’s political and artistic story; tickets often include access to Torre Grossa.
- Collegiata (Duomo di Santa Maria Assunta) — A compact cathedral whose interior is packed with well-preserved 14th-century fresco cycles (think Giotto-era storytelling), giving a real sense of medieval devotional life.
- Piazza della Cisterna — The photogenic, triangular well-square surrounded by medieval houses and towers; it’s the social heart of the town and an ideal place
- Torre Grossa — The tallest tower you can climb in town; the stairs are worth it for the 360° views over towers, vineyards and the Tuscan hillscape, and for feeling what a medieval lookout felt like.
- Palazzo Comunale (Civic Museum) — Right next to the Duomo, the palace holds civic frescoes, a small pinacoteca and period rooms that tell the city’s political and artistic story; tickets often include access to Torre Grossa.
- Collegiata (Duomo di Santa Maria Assunta) — A compact cathedral whose interior is packed with well-preserved 14th-century fresco cycles (think Giotto-era storytelling), giving a real sense of medieval devotional life.
- Piazza della Cisterna — The photogenic, triangular well-square surrounded by medieval houses and towers; it’s the social heart of the town and an ideal place to sip coffee and watch daily life unfold.
- Piazza del Duomo — The other major square, framed by the Duomo and Palazzo Comunale, where you can feel the civic and religious centers of medieval San Gimignano meeting in one open space.
- Rocca di Montestaffoli (the Rocca) — Ruined fortress and park behind the town with shaded paths and one of the best elevated viewpoints for sunset — less crowded than the towers and very pleasant for a picnic.
- San Gimignano 1300 (model museum) — A surprisingly charming, detailed scale model of the town as it was in the Middle Ages; it’s a quick, grounding way to understand why San Gimignano’s towers mattered.
- Chiesa di Sant’Agostino — A quieter church with atmospheric frescoes and local history that’s often less visited than the Duomo but just as interesting for people who like art without the crowds.
- Museo della Tortura (Torture Museum) — A small, touristy but tangible museum that shows medieval and early-modern instruments; not for everyone, but it gives a visceral sense of darker justice practices of the era.
- Porta San Giovanni & the city walls — Walk the medieval gate area and the surviving stretches of walls to appreciate how the walled town was defended and to frame your visit with authentic medieval infrastructure.
Spotted a mistake or missing something? Contact us.
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Hi, I’m Johan (Netherlands 🇳🇱), the creator of TakeYourBackpack. Over the past 3 decades, I’ve backpacked through 90+ countries across six continents, gaining extensive experience with independent travel, long-term trips, and overland routes.