In 1572 Cosimo I commissioned Bartolomeo Ammannati to build fortified wharves and docks to connect within a quadrangular perimeter the Old Fortress with the Lighthouse of the Pisans (Fanale dei Pisani). Three structures, Ferdinando Port, Cosimo Port, and Mediceo Port, were constructed.

Ferdinando Port was 1,340 feet long. It extended from the harbor opening inlet to the Old Dock near the old fortress. The Cosimo Port is perpendicular to the Ferdinando Port, and it is 788 feet in length. The Cosimo Port ends at the Sassaia Fort, a blockhouse built over the Sassaia reef.

The Mediceo Port is an extension of Cosimo Port extending from the Sassaia reef, northwest, and parallel to the coast. It is 1,544 feet long and 821 feet wide. At the end of the port is the Wharf Fortress (Fortezza del Molo), once used to guard the port entrance. Mediceo Port could accommodate as many as 140 deep-sea vessels in its heyday.

Terrazza Mascagni, known in English as Mascagni Terrace, is a piazza that overlooks the Ligurian Sea. The breathtaking square has a stunning black-and-white checkered floor that provides ample room for walking along the arm of the Mediterranean. There are a total of 34,000 tiles over 8,700 square meters (just over two acres).

The area was turned into a square in 1925 using a design by engineer Enrico Salvais. It was named afer composer Pietro Mascagni. Prior to this, Mascagni Terrace was the location for the Cavalleggeri Fort.

There are many notable spots within Mascagni Terrace. One of the most historically significant is the gazebo located in the southernmost portion of the square. The original gazebo was built by Ghino Venturi in the 1930s. It was destroyed during World War II but painstakingly rebuilt to look exactly like it did when it was new.

The Mascagni Terrace is home to the Livorno Aquarium, which allows patrons to learn more about the sea life of the Mediterranean. A swimming pool in the square is open to the public. It has a large slide with a stunning view of the sea.

Those wanting to take a break from sightseeing can rest on a sun bed. Each sun bed is equipped with a foldable umbrella to offer either sun or shade. There are several restaurants in and near the square and a large number of tables that are ideal for a quick bite while enjoying the atmosphere.

Other amenities at the Mascagni Terrace include walking paths, public restrooms and a playground for young children.

The Livorno Aquarium (Acquario di Livorno), situated on the scenic Terrazza Mascagni, offers visitors a deep dive into the wonders of marine life and beyond. Located near the Cetacean Sanctuary, this aquarium is home to an impressive range of aquatic species, amphibians, reptiles, and insects from all over the world.

As you begin your visit, the first room is dedicated to Diacinto Cestoni and introduces the vibrant biodiversity of the Mediterranean Sea. You’ll explore themed exhibition tanks like “The Crustaceans of the Mediterranean” and “The Colors of the Mediterranean,” where you’ll discover the rich underwater landscapes of this region.

Among the aquarium's many highlights are the Indo-Pacific tank, where Ari and Cuba, the star turtles, swim alongside zebra sharks, Napoleon fish, and blacktip reef sharks. Another crowd favorite is the tactile tank, offering visitors the unique chance to get up close and touch rays as they glide gracefully through the water. The jellyfish exhibit serves as both a visual spectacle and a gentle reminder of environmental conservation, raising awareness about the threat plastic waste poses to sea turtles and other marine creatures.

The aquarium also boasts a mesmerizing reproduction of a Greek-Roman shipwreck in its Mediterranean tank, where species like great sea bass and rockfish swim around the ruins. Moving through the exhibits, visitors encounter the vibrant world of the Caribbean Sea, home to colorful creatures such as the green moray eel, surgeonfish, and fire angel fish.

A visit to the panoramic terrace provides sweeping views of Livorno's coastline and an opportunity to reflect on the aquarium’s incredible displays. For those fascinated by land creatures, the tour concludes with a diverse range of amphibians and reptiles, including chameleons, iguanas, dart frogs, and leafcutting ants.

Ideal for families and travelers alike, the Livorno Aquarium blends education with an engaging, immersive experience, making it a must-see attraction on any visit to Livorno.

Viale Italia, or Italy Avenue, is a promenade that snakes along the seafront from the southernmost point of La Rotunda to the Piazza Luigi Orlando. Visitors to Livorno will find themselves on Italy Avenue often as it provides access to many of the city's most notable sites. However, it is worth the time to appreciate the street itself.

Most visitors can begin their visit of Italy Avenue at Regina Margherita Barrier. This is where the street offers excellent walking paths that are unencumbered by traffic. From there, visitors will pass such spots as the Italian Naval Academy, the Church of San Jacopo in Acquaviva, the Queen's Rock, the Gazebo Terrazza on Mascagni and the Livorno Aquarium, among many others.

The street is also known for shopping and dining. There are numerous dining options for those who want to try authentic Tuscan cuisine or enjoy a gelato. Visitors should also plan to buy souvenirs at one of the many shops along the street.

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.

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.

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.

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.

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.

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.