Table of Contents
Most travelers arrive in Livorno by cruise ship, they disembark and make a beeline for Pisa or Florence, leaving this fascinating port city completely off their radar. And sure, those iconic spots are incredible, but let’s take a moment to give Livorno the love it deserves.
This is no ordinary city. It was designed in the 16th century by none other than the Medici family (Florence’s legendary rulers), who also turned it into a groundbreaking social experiment. For centuries, Livorno thrived as a melting pot of cultures, religions, and traditions, setting the standard for coexistence and tolerance long before these ideas became a global talking point. And let’s not forget the canals: Livorno’s intricate waterway system is so impressive that even UNESCO has taken note.
Here’s what I learned during my visit and the experiences I enjoyed the most.
Livorno, a 16th-century ideal city
Livorno was a little more than a fishing village when the Medici set their eyes on it in. Back in 1421, they bought it from Genoa for the hefty sum of 100,000 gold florins. Why? Well, Florence was landlocked and desperately needed a direct link to the Mediterranean since Pisa’s harbor was clogging up with silt. So, Livorno was their golden ticket to the sea
The transformation began under Cosimo I de’ Medici, but it was his son, Francesco I, who took things to the next level. Francesco had a thing for alchemy and dreamed of turning Livorno into a model city inspired by the Renaissance ideals of rationality and functionality. To bring this vision to life, he enlisted the genius architect Bernardo Buontalenti—a man so inventive he’s even credited with inventing gelato. Yeah, that guy.
Buontalenti designed a fortified town enclosed within a pentagonal wall, guarded by imposing bastions. Surrounding this were canals that became the city’s main trade routes, lined with warehouses and cargo depots.
The Medici’s bold vision paid off. Livorno became a hotspot for Europe’s elite, a must-see stop on the Grand Tour. Percy B. Shelley spend time in town with her wife and even wrote an ode to the beauty of Livorno’s nature in the poem To a Skylark.
Morning at the Vettovaglie Market
I’m a sucker for markets, and this one in Livorno is like a treasure chest of history and food. Built over a century ago, it’s designed after the old Parisian halls, and fun fact – it’s the second largest covered market in Europe, with a whopping 4,800 square meters.
The architecture is like the lovechild of Neoclassicism and Art Nouveau, and inside? Pure bliss: bread, schiacciata (both salty and sweet), fresh pasta, meat, fish… and even one stall selling all sorts of eggs!
Don’t think it’s another tourist trap. The Livornesi actually come here to shop for their daily needs, so it’s a great spot to grab a coffee and soak in the lively, local chatter. Plus, you can always squeeze into the crowds by the stalls and grab a little treat.
And the fun doesn’t stop inside – the action spills out onto the streets too, with stalls selling all kinds of goodies and trinkets. You’ll also spot two local icons: Il Frataio Antica Friggitoria, where you can score the best frati in town (deep-fried, sugary doughnuts) and Gagarin, which I’ll tell you about in a sec.
Snacking on Livorno’s 5e5 chickpea sandwich
Take an unassuming local spot, reduce the menu to one legendary dish, and you’ve got an irresistible culinary experience you can’t help but go back for more. That’s what you get at Gagarin, a no-frills joint named after a Russian cosmonaut (because apparently the owner had a striking resemblance to the guy). Their specialty? The 5e5, Livorno’s famous torta di ceci (chickpea pancake) stuffed into a sandwich.
Now, 5e5 literally means “five and five,” because back in the day, locals would grab 5 Lire worth of bread and 5 Lire worth of chickpea pancake. It’s a delicious little tradition that’s still going strong today. You can choose between two types of bread—francesino or focaccia—and whether you want a slice of garlicky eggplant (trust me, you do). They’ll take care of the rest. And make sure to order a Spuma Bionda, it’s a sweet, fizzy, non-alcoholic drink that’s the perfect match for the 5e5.
Just a heads up: the place is tiny, so avoid the lunch rush unless you want to be stuck standing and eyeing other people’s sandwiches.
Navigating the canals, one of the best things to do in Livorno
When in Livorno, a boat tour along the canals is an absolute must. Trust me, it’s one of the best ways to soak in the city’s history while getting a completely different perspective on it. Picture this: gliding through canals built by the Medici back in the 16th century, with the city unfolding around you – magic!
The tour takes you along the old port and past maritime workplaces, with views of ancient palaces, old warehouses, and some seriously scenic spots. Here’s a fun fact: while you’re cruising, you’ll even pass under Piazza della Repubblica, which happens to be the widest bridge in all of Europe! Oh, and don’t forget to check out the Mercato Centrale too—it’s another gem.
I took the boat ride with Livorno Sailing, and it was a total winner. It’s about an hour long, and the guide was fantastic, filling us in on all the history, quirky anecdotes, and fun local trivia along the way. Highly recommend it!
Art in a beautiful villa
Venturing outside the city centre leads to more of Livorno’s unexpected surprises, like Villa Mimbelli, a stunning 19th-century property that once belonged to a family in the grain trade. Inside? Pure elegance—think frescoed walls, intricate ceramic cherubs adorning a stunning balustrade, and a vibe straight out of a period drama. Today, it houses the Giovanni Fattori Civic Museum, named after one of the leading figures of the Macchiaioli movement.
Now, unless you’re Italian or an art buff, you’re probably thinking, “The Macchiai what?” In short, the Macchiaioli were a group of Tuscan artists who rebelled against stuffy 18th-century aesthetics and academic rules. Instead of obsessing over perfection, they ditched the studio, headed outside, and started painting quick, bold sketches to capture natural light and mood. Their name, “Macchiaioli,” comes from the Italian word macchia, meaning “stain”—a jab from a snarky journalist that ended up naming an entire art movement.
Think of them like the Impressionists’ underrated older siblings. Technically, they were doing this 10 years before the French Impressionists came along, but, unfortunately, they didn’t get nearly the same level of fame.
Wandering through the museum, you’ll see how these artists brought their surroundings to life. There’s the bustling energy of the harbor in Vittorio Nomellini’s Il Moro and the dreamy fall vibes of Lodovico Tommasi’s La Caduta delle Foglie. My personal favorite? Renato Natali’s La Vigilia di Natale—the way he plays with color is just mesmerizing.
The museum also showcases portraits by Vittorio Corcos, who captured Italy’s high society in the early 1900s, and even a piece by a young Amedeo Modigliani, whose signature portraits with elongated necks became iconic. By the way, Modigliani was born right here in Livorno, and you can visit his childhood home on Via Roma 38, which is now a museum packed with his life story and art.
Browsing ex-voto at the Montenero Monastery
Still art, but with a different vibe. Perched on a hill with killer views of Livorno and its port, you’ll find the Montenero Monastery, home to the church dedicated to the Madonna delle Grazie. She’s not just the patron saint of Tuscany—she’s also got a reputation for working some serious miracles.
These miracles have inspired generations of grateful souls to leave behind ex-voto as tokens of gratitude for her divine intervention. And let me tell you, the collection is impressive—over 700 ex-voto, making it one of the biggest in Italy. Most of them are simple little paintings, created by not professional artists, and that’s what makes them so special. They’ve got this raw, almost childlike simplicity to them, yet you can feel the emotion pouring out of every stroke. They tell stories of near-death escapes—shipwrecks, fires, sickness, and other close calls with disaster. And in a way, these little paintings open a window to the past, giving us glimpses into how people lived—what they wore, where they walked, what their homes looked like.
One of the coolest pieces on display is a bodice and a pair of slippers that belonged to a Livornese girl kidnapped by Turkish pirates in the 1800s. She was hauled all the way to Constantinople, destined for the Sultan’s harem, but—plot twist—her brother somehow managed to buy her freedom. Yep, these ex-voto are full of incredible stories.
Join locals for a dive by the church
Piazza San Jacopo in Acquaviva, right on the seafront, is not just one of Livorno’s most scenic spots, but also the place where locals gather to soak up the sun, dive off a little pier lovingly nicknamed “the strip”, and gather for casual chats as the waves gently roll in. Yep, prime territory for some great people-watching!
The piazza sits in the shadow of the Church of San Jacopo in Acquaviva, which is steeped in history. Back in the day, a fresh spring flowed here, and its medieval crypt still holds an altar carved straight out of the rock. Centuries ago, pilgrims would embark from this very spot, heading to France or Spain to begin their journey to Santiago de Compostela. Just behind the church, you’ll find the prestigious Naval Academy, where Italy’s future navy officers are trained.
As if that weren’t enough, this piazza marks the grand finale of the Way of San Jacopo, a 170-kilometer walking route that starts in Florence and winds through some of Tuscany’s most iconic cities—think Lucca, Pisa, and Pistoia—before landing you here.
Sunset at Terrazza Mascagni, a must-see in Livorno
From Piazza San Jacopo in Acquaviva, a delightful seafront walk takes you to Terrazza Mascagni, Livorno’s iconic chequered terrace. The visual impact is very strong: a vast chessboard of white-and-black tiles stretching out to meet the sparkling blues of the sea, with the sky painting itself in shades of pink and orange as the sun sets. Wow.
But Terrazza Mascagni wasn’t always the dreamy terrace it is today. Once upon a time, there was a fortress here, then a carnival park, before it evolved into this grand public square. And when I say grand, I mean it—over 34,000 tiles covering a total od 8,700 square meters—complete with an elegant round temple for concerts.
The terrace is named after Pietro Mascagni, a famous Livorno-born composer. On warm days, you’ll find kids zipping around on bikes or roller skates, kites flying high in the breeze, and the sound of laughter everywhere—another beautiful snapshot of pure Italian life.
The Livornine Laws at the Jewish Museum
In their effort to transform Livorno into an ideal city and one of the most prominent ports in the Mediterranean, the Medici introduced the so-called Livornine Laws. These laws allowed individuals of any nationality, ethnicity, religion, and social background to settle in the city, offering them immunity from past debts or crimes—talk about a fresh start!
The laws proved incredibly successful, turning Livorno into a vibrant melting pot of cultures. One of the most prominent and influential communities to settle there was the Jewish community, which made up a quarter of the city’s population by the 18th century. Thanks to their presence, Livorno became Italy’s first port to import coffee and the location of the country’s very first café long before the famed Florian Café in Venice.
But, as history goes, things took a dark turn in the 20th century with the racial laws, forcing many Jews to leave the city. Today, the Jewish Museum is an important piece in understanding Livorno’s rich history. Once a secret school during the fascist and Nazi regimes, it now holds precious artifacts from the monumental synagogue that was destroyed during World War II, as well as ceremonial art pieces, items brought through trade, and works created by the Jewish community itself. One example is the beautifully crafted coral objects, a specialty of the Livornese Jews. But the most fascinating exhibit for me is the original Livornine Laws issued by Grand Duke Ferdinando de’ Medici.
The museum is located on Via Micali, just a 15-minute walk from the central market. It’s open by appointment, so be sure to contact Mrs. Gilda at amarantaservizi@gmail.com to arrange your visit.
Visiting a church with 1,500 square meters of frescoes
In the charming Venezia district, the Church of Santa Caterina is a little jewel to visit. The façade is a bit rough, almost minimalist. Yet, step inside, and it’s a whole other world. The octagonal floor plan is flanked by side chapels and towering windows, and all around are Baroque decorations and marble columns. Oh, and you’ll find some charming ex-voto paintings here too.
The real surprise is the inside of the massive dome: it’s one of the largest frescoed surfaces in whole of Tuscany, covering a massive 1,500 square meters. And as you stand there, looking up in awe, you’ll find the grand altarpiece: a stunning painting by Giorgio Vasari, The Coronation of the Virgin, whose sketch is at the Louvre in Paris.
And here’s a fun fact: Elizabeth Ann Bayley Seton, the first American ever to become a saint, prayed here. You’ll find an epigraph to remember that historic moment.
Exploring Livorno’s Venezia Nuova under the stars
A nighttime stroll through Venezia Nuova is absolutely one of the best things to do in Livorno. This area was created in the 17th century at the request of the merchants who flocked to the city thanks to the Medici’s Livornine Laws. They needed more space to carry out their business, and voilà, a whole new part of the city was born.
Fast forward a few centuries, and the place still has an undeniable charm: tall buildings with faded façades, old warehouses, and the soft glow of streetlights reflecting in the brackish waters of the canals. Oh, and the name? Venezia Nuova (New Venice) comes from the fact that the construction of these canals, which were connected to the port to ease the loading and unloading of goods, was inspired by techniques and laborers imported directly from the Venetian lagoon!
Look for the Ponte di Marmo bridge and look for the inscriptions carved into the stone by dockworkers and boatmen, many dedicated to comrades lost at sea. Though most of these inscriptions are barely legible now, they’re a priceless window into that fascinating time.
How to travel to Livorno
The nearest airport is the “Galileo Galilei” di Pisa (about 18km away) and from there a taxi. Alternatively, the “Amerigo Vespucci” airport in Firenze is 80 km away: catch la linea T2 della tramvia to the S.M. Novella train station and from there it’s a bit more than an hour train ride to Livorno.
If you’re traveling Italy by train, you can find direct trains from major cities like Florence (1.5 hrs), Genoa (3 hrs), and Rome (3.5 hrs).
When driving, consider that the historic center has ZTL zones and parking on the street can be quite expensive (2.5-3€/h). So, better to leave the car in a parcheggio custodito such as the Cecconi costing 1.50€ per hour up to a maximum of 13€ per day. It’s about 15-minute walk to the Vettovaglie Market
Finally, Livorno is a major hub for cruises and ferris. Getting from the port of Livorno to the city center. When arriving at the port, you should find navette gratuite delle compagnie navali che portano vicino al centro storico. Or you can take Line 5 to Via Grande.
Ciao for now,
