The Old Fort stands at the entrance to Livorno’s harbor and represents the city’s earliest phase as a strategic port. Long before Livorno was conceived as a planned Medici city, this site already controlled access to the coast and shipping routes. Over several centuries, it evolved from a medieval stronghold into a Renaissance fortress.

The fortress assumed its present form beginning in 1519, when a new defensive complex was commissioned by Cardinal Giulio de’ Medici, the future Pope Clement VII, and designed by Antonio da Sangallo the Elder, one of the leading military architects of the Renaissance. Completed in 1534, the fort integrated earlier structures into a modern artillery-resistant design. Its layout is defined by three major bastions, Ampolletta on the landward side, Canaviglia facing the port, and Capitana to the northeast.

Beneath this Medici construction lie much older elements. The oldest surviving part in the Old Fort is the Keep of Countess Matilda, which is also the oldest surviving structure in Livorno. The keep is traditionally linked to Matilda of Canossa and dated to the early 11th century. In 1377, the Republic of Pisa incorporated the tower into a larger fortress known as the Quadrature of the Pisans, establishing the site’s long-standing defensive role. Within the Medici fortress stands the Church of Saint Francis of Assisi, built in 1530, where in 1606 the ceremony officially proclaiming Livorno a city took place.

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.

The New Fort was built in the late 16th century, shortly after the Old Fort, forming part of an ambitious Medici strategy to secure Livorno’s harbor and control access to the port. Unlike medieval fortresses that evolved gradually, the New Fort was conceived as a modern military structure, shaped by Renaissance engineering and a clear vision of Livorno’s future as a major Mediterranean port.

The fort’s design is closely linked to Bernardo Buontalenti, a Florentine polymath. In 1576, Buontalenti proposed the "Buontalenti Pentagon", a comprehensive defensive system enclosing the settlement. The New Fort itself was built on a canal-surrounded island within this defensive network, and even today the structure appears almost like a fortress rising directly out of the water. As Livorno expanded, parts of the fortifications were modified to allow the growth of commercial districts.

For centuries, the New Fort remained an active military installation and later served additional roles, including use as a prison. Heavily damaged during the Second World War, it was restored by 1972 and reimagined for civilian use. Today, the New Fort functions as a public park and cultural venue. Inside the walls, visitors can walk across grassy lawns and along gently rising ramparts, where the fort’s angular bastions and thick masonry remain clearly visible. Traces of embrasures, walls, and defensive geometry survive throughout the site, while the broad interior space is now used for quiet walks, informal gatherings, and occasional cultural events.

Republic Square was designed as a monumental structure built over water. Created in the 19th century by covering part of the Royal Canal system, the square is famously known to locals as Bridge Square. Beneath its surface lies the Great Vault, a vast elliptical vaulted structure that continues to carry canal water below.

This immense masonry vault is considered a notable achievement of 19th-century engineering, allowing the city to expand its civic space without abandoning its canal-based layout. Seen from above, Republic Square takes on a distinct oblong, elliptical shape, intentionally modeled on the grand urban “place” tradition popular in contemporary Parisian planning. Broad facades and continuous building lines frame the square.

At the south end of the oval stands the statue of Grand Duke Ferdinand III and at the north end stands Leopold II, both being rulers of the Lorraine dynasty under whom Livorno underwent major transformation. Their presence reflects the period when Livorno was strengthened as a free port, attracting merchants, artisans, and foreign communities. Just nearby, the New Fort, a 16th-century Medici defensive fortress, lies north-west of the square, across the canal.

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.

The Central Market is Livorno’s principal food market and one of the city’s most revealing civic spaces. Its creation belongs to the period of urban renewal that followed the unification of Italy, when many cities underwent a process known as remediation, reshaping infrastructure and public services. The market was conceived as a modern solution for food distribution, reflecting the late-19th-century enthusiasm for iron-and-glass architecture inspired by similar market halls across Europe.

Construction began in 1889, following the demolition of sections of 17th-century fortifications, and the building was completed in 1904. The market occupies a long rectangular footprint overlooking the Royal Canal, with a facade extending roughly 312 feet. Entrances are placed on all four sides, with the main access aligned with Street of Our Lady. Arched windows, Corinthian columns, and pilasters articulate the exterior, while a smaller upper structure and double roof system crown the building.

Inside, the market is organized around a spacious central hall animated by decorative caryatids, with high ceilings and generous natural light. Surrounding halls are dedicated to specific trades: one primarily for fish, another for fruit and vegetables, alongside stalls offering meat, cheese, bread, and local Tuscan specialties. The scale is substantial, with hundreds of stalls and shops, making it one of the largest covered markets in Italy.

The Main Street is Livorno’s main commercial artery, stretching from the Mediceo Port toward Republic Square and forming a direct link between the harbor and the city center. Laid out as part of Livorno’s original Medici planning, the street was designed to handle movement of people, goods, and daily life. Today, it remains one of the busiest and most recognizable routes in the city, especially for visitors arriving by sea.

The street functions as Livorno’s primary shopping corridor, lined with a mix of international fashion brands, shoe stores, jewelry and perfume shops, alongside cafes and smaller local businesses. The postwar reconstruction of the 1950s reshaped the street with modernist buildings and a simplified layout. While this altered its appearance, the street retained its original role as Livorno’s commercial backbone.

Offering insight into Livorno’s everyday rhythm, you pass through Grande Square, the city’s central civic space, rebuilt after the war and anchored by the Livorno Cathedral. On the northern edge of the square, facing the Cathedral, you see the Gran Guardia Loggia, connected to civic order and public authority.

Walking east, the route reaches Guerrazzi Square. Here stands the Monument to Francesco Domenico Guerrazzi, a writer and political figure of the Risorgimento, whose presence reflects Livorno’s strong republican and revolutionary tradition. Nearby, the Poccianti Cistern recalls the city’s 19th-century water infrastructure, while the Picchetto Palace marks the site of a former military checkpoint controlling movement along the street. The walk concludes at the historic Pisa Gate, once a main entrance to the city, now demolished, just before Main Street meets Republic Square.

The Livorno Cathedral, officially dedicated to Saint Francis of Assisi, reflects the city’s status as a planned Medici foundation. Construction began in 1594 and was completed in the early 17th century, forming part of a broader effort to provide the new port city with a religious and civic center suited to its growing importance.

The cathedral was designed in a restrained late-Renaissance style, traditionally attributed to architects working within the Medici circle, including Alessandro Pieroni. Its original design favored balance and clarity over ornament, with a broad facade, measured proportions, and a spacious interior intended to accommodate large congregations. This sobriety echoed Livorno’s practical character and distinguished the cathedral from the more ornate churches of inland Tuscany.

The cathedral was largely rebuilt in the 1950s. As a result, much of what visitors see today reflects postwar reconstruction rather than the original interior. The rebuilt church preserves the historical basilica layout, with a wide central nave flanked by side chapels and a clear axial progression toward the high altar. The interior is notably bright and uncluttered.

Within this reconstructed space, artworks salvaged from the original building or reintroduced after the war provide points of historical continuity. These include altarpieces, devotional paintings, and liturgical furnishings that recall the cathedral’s earlier phases.

The Monument of the Four Moors is Livorno’s most recognizable public sculpture. Erected in the early 17th century, it reflects both the artistic taste of the period and the political ambitions of the Medici. The monument was commissioned in 1617 by Cosimo II de’ Medici, the Grand Duke of Tuscany from 1609 to 1621, in honor of his father, Grand Duke Ferdinando I, and completed in 1626.

At the center of the monument is a marble statue of Ferdinando I, dressed as a Knight of the Order of Saint Stephen, the naval order founded by the Medici to combat piracy and assert control over the Tyrrhenian Sea. The figure stands atop a high pedestal, gazing toward the harbor. Surrounding the base are four bronze figures, sculpted by Pietro Tacca, a leading Mannerist and early Baroque sculptor. These figures represent defeated corsairs, bound in chains at each corner of the pedestal.

The four bronze statues belong to a wider 17th-century sculptural trend in Italy that favored expressive depictions of prisoners, captives, and enslaved figures. Each Moor is physically distinct, suggesting different geographic origins within the Mediterranean world and beyond; one figure is clearly African, while others reflect North African or Middle Eastern features. Tradition holds that Tacca used real prisoners as models.

The monument projects Medici maritime power and authority, while also unintentionally revealing darker realities of the period, including slavery and forced captivity, in which Tuscan interests were not innocent observers.