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The world's smallest and oldest republic, as San Marino dubs itself, is surrounded entirely by Italy. It consists of three ancient castles perched on sheer cliffs rising implausibly out of the flatlands of Romagna, and a tangled knot of cobblestone streets below that are lined with tourist boutiques, cheesy hotels and restaurants, and gun shops. The 1½-hour drive from Faenza is justified,
however, by the sweeping views from the castle of the countryside. The 3,300-foot-plus precipices will make jaws drop and acrophobes quiver.
Visiting San Marino in winter—off-season—increases the appeal of the experience, as tourist establishments shut down and you more or less have the castles to yourself. In August every inch of walkway on the rock is mobbed with sightseers. Don't worry about changing money, showing passports, and the like (although the tourist office at Contrada del Collegio will stamp your passport for €2.50). San Marino is, for all practical purposes, Italy—except, that is, for its majestic perch, its gun laws, and its reported 99% national voter turnout rate.
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The Via Emilia runs through Emilia's heart in a straight shot from medieval Piacenza, 67 km (42 miles) southeast of Milan, through Bologna,...