Leghorn is very different from the other main cities of the Tuscany; it hasn't a medieval or Renaissance origin but it presents a character, an history and an urban development much more recent. It was founded as a link between the sea and the port facilities of the most important Pisa. There was only a Castle and a small port next to a Fortress, which, enlarged by the Florentines in the early decades of the 1500s, was called the Old Fort and became one of the greatest defensive systems of the Tuscan State. Between the XVI and XVII century was built the imposing New Fortress that was part of the grand project of Leghorn as a city-fortress commissioned by Grand Duke Francesco I de 'Medici to the Buontalenti.

Leghorn is a strange and a fascinating city for its location on the sea for which he had to build buildings and squares in a singular manner: the current Republic Square was built in 1844 by the architect Luigi Bettarini and was called "The Voltone" because designed on a great vault built over the Fosso Reale. Along the Fosso Reale was built in 1894, the Central Market an imposing building with the main facade 95 meters long. The entrance is composed of four columns supporting a massive entablature where a sign indicates both the use of the building “Nuovo Mercato delle Vettovaglie” and the name of the Engineer Architect who designed the building: Angiolo Badaloni.

A splendid Seafront walk, often depicted in paintings by the Macchiaioli school, runs through trees, cliffs, rocks and beaches (sand and shingle). This front begin in the Port of Leghorn, characterized by the Old Medicean Fortress and runs for nine enchanting kilometers to the village of Antignano. Viale Italia leads to a wide Belvedere that in the early decades of the 1900s was transformed into a large square with a gazebo for the music, a sort of small round temple, with the domed roof supported by a series of round columns. Expanded in the postwar period, it was called Mascagni Terrace, in honor of the famous musician born in Leghorn.