Countess Matilda, Margrave of Tuscany in the 11th century, built a tower called the Keep of Countess Matilda. The tower was later incorporated into a fort built by the city of Pisa in 1377 called the Quadrature of the Pisans. These two structures were later the foundation of a new castle built by the Medici family, known now as the Old Fort.

Cosimo I de Medici started building the Old Fort in 1519. It was completed in 1534. The church of Saint Francis was built in the fortress in 1530. It was here, in 1606, that the ceremony proclaiming Livorno as a "city" took place.

There are three bastions and two gates. The landside bastion is called Ampolletta. The portside bastion is called Canaviglia. In the northeast is Capitana.

For centuries, the Old Fort has dominated the city skyline and is an iconic symbol of Livorno.

The Medici family made numerous modifications to the fort until the end of their dynasty in 1737. More changes were made during the Napoleonic era and later in the 19th century. Today, the Old Fort is managed by the Livorno Port Authority. The fort is open Tuesdays through Sundays from 9 am to 8 pm. Admission is free.

New Venice (Venezia Nuova) is a historic district in Livorno, known for being one of the few areas in the city center that largely retained its architectural heritage despite the destruction of World War II and subsequent reconstruction. While not the original Medici Livorno nucleus, it has become the city's true historic center, preserving its essence and charm.

The district was developed between 1629 and 1645 to accommodate Livorno’s burgeoning merchant class, which flourished thanks to the abolition of customs duties and inclusive policies initiated by the Medici Grand Dukes. These policies attracted merchants and traders from all over the world, transforming Livorno into a thriving commercial hub. The neighborhood's construction drew inspiration from Venice, with the use of advanced techniques imported from the Venetian lagoon to build over what was once a partially submerged area.

New Venice is characterized by its tall houses, distinguished by their blond plaster facades in shades of pink and green, catching the sun's light in golden and verdigris reflections reminiscent of the oil-slicked canal waters. These homes, with their pale, dusty shutters, convey a mix of faded nobility and popular freedom in their open architecture, embodying the Mediterranean's architectural beauty.

The district is home to two significant religious landmarks: the Church of San Ferdinando Re, associated with the Trinitarian order, and the octagonal Church of Santa Caterina, built by the Dominicans. Both churches reflect the artistic and spiritual vibrancy of the district during its peak in the 18th century.

Every summer, New Venice becomes the vibrant stage for "Venice Effect," a folkloristic event where the streets are filled with stalls, shows, and cultural celebrations, breathing life into the historic canals. Additionally, the district hosts a winery that actively participates in Livorno’s traditional rowing competitions, adding to its rich cultural fabric.

Cosimo I and his son, Francesco I de Medici, commissioned a lot of work to Bernardo Buontalenti. Buontalenti was a renaissance man with many talents. He was a stage designer, architect, theater designer, military engineer, and artist. But best of all (to some), he invented Italian ice cream (gelato). In 1575 he made a plan to remake Livorno.

His plan was called the Buontalenti Pentagon. It enclosed the old city and its Old Fort within a pentagonal system of canals. Buontalenti's plan became the New Fort by adjusting the San Francesco Rampart and the Santa Barbara Rampart. The result vastly strengthened the military defensiveness of the town.

Buontalenti's project was further ameliorated by Don Giovanni de' Medici, Claudio Cogorano, and Alessandro Pieroni. The project was completed in 1604. Ferdinando II de Medici, Grand Duke of Tuscany, demolished part of the fortress in 1629 to facilitate the building of the New Venice and San Marco commercial centers of the city.

The New Fort was a military facility until the end of World War II. It had barracks for personnel and a chapel dedicated to the Immaculate Conception. The fort suffered severe damages in the war, and it was restored by 1972. Presently it serves as a public park and as an events venue.

In 1575, Francesco I de Medici commissioned Bernardo Buontalenti to put forward a plan to turn Livorno from a glorified fishing village into a fortified town with a promising future. Buontalenti's solution encompassed the Old Fort and the original village. He presented a pentagonal system of walls, bastions, and canals.

In 1844 there was a need to connect the Buontalenti Pentagon of 1575 with the eastern part of town, which stretched well beyond the Royal Canal. The project would require the demolition of the city gate and modify the Royal Canal. Architect Luigi Bettarini had an idea: cover the canal.

Bettarini's concept was to put the canal in a vault. The vault cover is 789 feet long and 296 feet wide, and it became a public square. The waterway would still be navigable and would pass under the square. The popular name of the new place was Vault Square (Piazza del Voltone). In 1850 it was called the Square of Grand Dukes (Piazza del Granduchi). In 1859 it was named for Carlo Alberto, a leader of the first War of Independence.

In 1946, the square became the Republic Square (Piazza della Repubblica). It is furnished with 52 marble benches and 92 pillars reminiscent of hitching posts. There are two statues on opposite sides of the square; one of Grand Duke Ferdinand III, Grand Duke of Tuscany, and another of Leopold II, son of Ferdinand III and the last reigning Grand Duke of Tuscany.

Also located in the square is the Cisternino, a neoclassical structure of the 19th century built to provide the city with water.

The Leopoldine Walls (Mura Leopoldine), also known as the Lorraine Walls, were constructed in the 19th century to define the boundaries of Livorno’s free port. Initially built for customs purposes, these walls played a significant role in the city’s economy and defense. Grand Duke Leopold II of Lorraine, responding to the requests of merchants eager to benefit from expanded trade opportunities, approved their construction in 1834. The walls aimed to curb smuggling and encompassed the city center and its growing suburbs.

Work on the Leopoldine Walls began in 1835, under the supervision of engineer Alessandro Manetti, with architect Carlo Reishammer contributing to the design of gates and access points. Stretching about 6 kilometers, the walls connected key points in the city, including Fort San Pietro to the north and Mazzini Square (Piazza Mazzini) to the southwest. The walls were topped with crenelated brick to thwart smuggling activities, making it difficult to use ropes for illegal trade.

Despite their primary function as customs boundaries, the walls were briefly used for defense during an 1849 uprising against the Austrian forces occupying Livorno. Later, even with the abolition of the free port in 1868, the walls continued to serve a municipal duty function.

In the late 19th and early 20th centuries, the walls were partially demolished to accommodate urban expansion and new transportation routes. By 1912, many sections had been removed, though portions near the port and a small surviving tower at Porta a Mare remained intact. Bombing during World War II and subsequent neglect further diminished the structure, but efforts in the early 2000s led to the preservation and integration of some sections into public green spaces.

The Palace of Larderel in Livorno is a striking example of 19th-century architecture, renowned for its grandeur and connection to the industrial rise of François Jacques de Larderel, a French entrepreneur who settled in Livorno after the revolution. Situated between the Cisternone and Republic Square (Piazza della Repubblica), the palace now houses the Civil Court of Livorno.

De Larderel, who played a key role in exploiting boraciferous blowers in Montecerboli, commissioned the construction of the palace in 1832 after purchasing land along Via dei Condotti Nuovi. Initially designed by Riccardo Calocchieri, the building underwent significant expansions, including two lateral wings by Gaetano Gherardi and later a unified façade by Ferdinando Magagnini. The façade, which spans 80 meters, bears resemblance to the Belgian Palace (Palazzo Belgioioso) in Milan, featuring symmetrical openings, a long central balcony, and detailed sculptures by Luigi Magi symbolizing commerce, mechanics, and agriculture.

Inside, though much of the original furnishings are lost, the palace retains its grand architecture. The vestibule showcases plaster statues of notable Tuscans, while the grand staircase, completed in the late 19th century, is adorned with additional statues. Noteworthy rooms include the dining room and party room, designed by Gherardi, with neoclassical-inspired decorations. The upper floor holds the once-famous Red Room or Grand Gallery, originally home to the count's art collection, characterized by a glass roof and paintings celebrating the family's prestige.

Other remarkable features include the ballroom, with its Ionic columns and classical bas-reliefs, and the Gothic Cabinet, an opulent neo-Gothic room crafted by Magagnini, boasting gilded wooden arches and mullioned windows. Despite some loss of its original decorations, the palace remains a testament to the de Larderel family's influence and the architectural splendor of 19th-century Livorno.

Central Market is the main market in Livorno. After the unification of Italy in the 19th century, several major cities, Livorno among them, went through a renewal period called "Risanamento" (Remediation). The market was the result of the rage for iron and glass that followed.

Construction started in 1889 after the demolition of some 17th-century fortifications. The work was completed in 1904. The facade is 312 feet long, overwhelming the Royal Canal. It is rectangular, with an entrance on each of its four sides. The Main Entrance is at the end of the Street of Our Lady (Via della Madonna).

Arched windows line the side walls flanked with Corinthian columns and pilasters. The upper floor is a smaller similar structure, a double roof centered on the ground floor roof. The main hall of the interior is graced with caryatids. The arched windows on the top walls and the double roof afford generous light for the high-ceilinged market rooms.

In the main hall, shops display the foods of Tuscany for the most part. Two other rooms sell fish and vegetables. The fish room has 22 marble counters. The veggie room has 22 vegetable stands. The total market capacity is 230 stands or stalls and 24 shops. In fact, Livorno's Central Market is the second largest indoor market in Europe, second only to the Boqueria Market in Barcelona.

Livorno has a well-deserved reputation for its religious tolerance. Jews were free to live within the walls, escaping the kind of persecution that they encountered in other parts of Europe. The Jewish influence can be found today in the kosher fish and tomato-based dishes seen in the market.

Main Street (Via Grande) Livorno’s vibrant shopping artery, extends from the Medicean Port to Republic Square. As one of the city’s major thoroughfares, it is a hub for both locals and tourists, particularly those arriving via cruise ship. This bustling street is lined with familiar high-end clothing stores, shoe shops, and various outlets for jewelry and perfumes, making it a prime destination for those seeking retail therapy. International brands such as Benetton, Max Mara, and Zara dominate the landscape, though a handful of local boutiques, cafes, and smaller shops offer a more personalized shopping experience.

The street is hard to miss, especially for cruise visitors, as shuttle buses drop passengers right in the heart of Via Grande. From here, it’s an easy stroll to nearby attractions, including the upscale Ricasoli Street, famous for its luxury boutiques, and Piazza Grande. A supermarket, Conad, is conveniently located at the west end of the street.

Operating hours for most stores are from 9 am to 1 pm, followed by an afternoon break, with doors reopening from 4 pm to 8 pm. Sundays and public holidays typically see the shops closed, although the first Sunday of each month is an exception, when most shops open in the afternoon (except during July and August). In August, many smaller shops close for a few days due to local holiday traditions.

With its mix of international brands and local charm, Via Grande serves as the perfect starting point for exploring Livorno’s shopping district, offering a blend of modern retail and traditional Italian flair.

The Livorno Cathedral is also known as the Cathedral of Saint Francis of Assisi, Mary Mother of Jesus, and Julia of Corsica. Julia, a patron saint of Livorno, was martyred in Cosica by Vandals in the 5th century. The cathedral is within the Buontalenti Pentagon on the south side of the Main Square (Piazza Grande).

Construction began in 1581. The facade is plain. The lower half has a porch with three arches supported by four Doric columns. The upper part of the facade has a central rectangular window within a recessed arch. Arches on either side are filled in and framed with pilasters. Restorations were made after World War II.

The original church had a rectangular plan with a single nave. It was changed to a cross plan when two chapels were added in 1716. The left chapel is dedicated to the Eucharist (the Christian service in which bread and wine are consecrated and consumed). The right chapel, dedicated to the Immaculate Conception, was built in 1727.

The Livorno Cathedral was almost destroyed, by Allied bombs, in World War II. It was rebuilt close to the original, except for the additions to the facade and transepts. The cathedral was reconsecrated in 1952.

When visiting the cathedral, make sure you see the painting "Christ Crowned with Thorns" by the early renaissance Italian painter Fra Angelico in the Chapel of the Eucharist. Fra Angelico is described, by the famous Italian art historian Giorgio Vasari, as having "a rare and perfect talent." He is known for his beautiful fresco paintings.

There was a sculptural fad in Italy in the 17th century that featured figures of prisoners and slaves, especially African slaves. The Four Moors statues in Livorno appear trendy that way. In 1617 Cosimo II commissioned Mannerist and Baroque sculptor Pietro Tacca to create a monument to Cosimo's father, Ferdinando I.

These four statues were meant to celebrate Roman aristocrat and general Marcantonio Colonna's role in the defeat of the Ottoman fleet at Lepanto in 1571. The joke was on Marcantonio. While he was sinking the Ottoman navy, the Ottoman army was sacking Cyprus.

Dressed as a Knight of San Stefano, Ferdinando stands on a high square pedestal in Micheli Square. A prisoner is chained at each corner of the base. One of them is African, perhaps a slave.

The Four Moors feature the four corners of the world. They also seem to tell the Medici's involvement in the slave trades in West Africa in the 17th century. Fernando II, the grandson of Fernando I, oversaw the monument's completion in 1626.