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The first stop on any tour of the area would have to be Livorno, one of the most important ports in Italy and home to the Italian Naval Academy.
The city still preserves the charm and layout conferred upon it by the Medicis in the 16th and 17th Centuries: the pentagonal defensive wall surrounded by navigable moats, the distinctively red-colored fortifications such as the Old Fortress or Fortezza Vecchia, work of Antonio da Sangallo; the Cathedral and the Via Grande portico.
The Venezia Nuova district is also rather charming, built in the 17th Century on the model of the original lagoon city; it includes a dense network of canals with bridges and high buildings, and is home to many fashionable bars and typical restaurants.

The Church of Santa Caterina is of particular artistic importance, while the Sanctuary dedicated to Santa Maria delle Grazie, located not far from Livorno in the village of Montenero, is of great religious significance.
In terms of outstanding architecture, the Cisternone and the Cisternino stand out; these two large reservoirs in the Neoclassical style, by architect Poccianti, are nowadays used as venues for cultural events.  Do not miss the Giovanni Fattori Civic Museum, located in the beautiful Villa Mimbelli, which houses a magnificent collection of Tuscan paintings realized between the 19th and 20th Centuries, and more works by Fattori.

Obviously no trip to Livorno is complete without Terrazza Mascagni,  a very special terrace made with stone balustrades that sweeps gracefully along the seafront in a dramatic chessboard flurry of black-and-white checks.

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