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This industrial port town, the second-largest city in Tuscany, is often overlooked for its more attractive Tuscan cousins like Pisa and Florence but is worth a stop, if for nothing else than its famed seafood restaurants. Livorno is also known as “Little Venice” due to its network of small canals. No trip to Livorno is complete without taking a stroll on Terrazza Mascagni, an elegant black-and-white-checkered boardwalk with stone balustrades located on the seafront.

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