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The region of Umbria itself could be classified as "off-the-beaten-path," in that it is the only landlocked province in all of Italy. This fact, however, gives it the distinction of being a little more rustic and quaint than its counterparts. There are countless little villages, views, and sites that are views that are not mentioned in any of the guidebooks, but that's all right. You'll discover them and have them all to yourself.
Return to the Middle Ages with a visit to Rocca del Leon (the Lion Fortress), located in Castiglione del Lago. With its subterranean passageways and high turrets, the adventurer (translation: kid) in you will be easily satisfied. The tiny hamlet of Lippiano has, of all things, a castle, built in medieval times.
In fact, you'll find a lot of medievalism in your travels around Umbria, much of it defined by stone castles, churches, lovely fountains in the city squares, even in the smaller villages. Spoleto sports an ancient stone aqueduct built by the Romans, as well as a Roman theater.
Though the ancients may have resented the invading Roman hordes that conquered much of Europe before their empire finally disintegrated, moderns appreciate Roman feats of architecture, such as the aqueduct mentioned above, and the ruined Roman baths in Bevagna, where you can still see parts of the original mosaic floor. Nearby is an amphitheater, and you can almost imagine a togad actor flourishing (cautiously) across the old amphitheater stage.