Tiny Monteriggioni makes a nice stop on the way north to Colle di Val d'Elsa, San Gimignano, or Volterra. It's hard to imagine that this little town surrounded by poppy fields was ever anything but sleepy, but in the 13th century Monteriggioni served as Siena's northernmost defense against impending Florentine invasion. (It's likely that the residents of the town spent many a sleepless night.) The town's formidable walls are in good condition, although the 14 square towers are not as tall as in Dante's (1265–1321) time, when the poet likened them to giants guarding the horrifying central pit of hell. The town empties of day-trippers at sundown, and this hamlet becomes very tranquil.

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