Trip Ideas - 6 min read

Tuscany’s Off-the-Beaten-Path Itinerary

Town and Tourist

Town and Tourist, Updated April 10, 2023

lorence has no shortage of attractions, from the Uffizi’s Gallery to the Boboli Gardens or just strolling around near the Duomo. But there are places to visit to immerse yourself in the local culture and chat with locals. 

Although this post starts in Florence, we’ll talk about exciting things to do beyond the obvious. Then, we’ll find two cities you cannot miss in Tuscany: Siena and Livorno.  

See Florence from a Florentine’s Point of View. 

A view of the bridges over the Arno from the Uffizi Gallery

Nothing is as beautiful as standing on the Ponte Vecchio and looking at the Arno with its seemingly endless bridges. But it is even better to discover Tuscany from an Italian perspective. 

How can you meet Italians and discover those hidden treasures? You can install a chat with locals app, like Playsee, to watch videos with recommendations and ask Florentines about exciting places. Connecting with those in the local community  will allow you to gain local knowledge about the area, and it will enrich you with authentic local experiences. From learning how to prepare real Italian food to immersing yourself in Italian art and culture like a local, you only have to gain from connecting with local people. 

Florence’s landscape and architecture have inspired countless artists. You can immerse yourself in the art of Florence by taking a painting workshop. While staying in the center is expensive, you can find affordable rentals outside the historical center and close to your art school. 

We rented a room near an Art School about 10 minutes from the Duomo. The 15th-century building was beautifully conserved, with a coffee shop and canteen overlooking a stone-paved patio. Enjoy an expresso and a berry pie on the patio for a quiet afternoon and talk about art with the other students. 

To go to the Duomo, follow Via Cavour and walk for about 15 minutes. Along the way, you can find several coffee and leather shops, colorful leather bags, and a fraction of the price in the historical center.

Enjoy Florentine spinach pie- the Torta Pasqualina and chickpea flour savory cake. I found an excellent bakery on a block before the Ponte Vecchio. You can learn to make it by enrolling in an authentic Florentine cooking class. I used the app to ask for recommendations from locals. 

After you enjoy the art and food from Florence, it is time to continue your journey to another Tuscany gem: Siena. 

Part 2- Travel through time in Siena

Siena is a short trip from Florence. At only 1.30 hrs by train, you can easily visit Siena on a day trip. 

Why should you add Siena to your Tuscany itinerary? For starters, Siena is one of the best conserved medieval cities in Europe, and unlike other Italian cities, reaching the historical center by public transportation is very straightforward. You can take a local bus from the central train station and arrive at Siena’s central historical landmark: Piazza del Campo. 

Walking from the bus stop to the piazza takes you back in time. Soon you find yourself in a medieval city with narrow cobblestone streets and high stone buildings. 

Arriving at the Piazza del Campo is an experience by itself. At first glance, it seems like any other medieval Italian town square: four sides surrounded by buildings in a gallery, a palace, and a clock tower. Soon, you’ll realize what makes it unique: the fan-shaped piazza consists of several sections inclined toward the center. So if you feel you are walking downhill, you’re right. 

If you are lucky enough to go to Siena in July, you can experience a local festival and the reason for this particular architecture: The Palio di Siena. In July and August, locals and tourists concentrate on the square to watch a unique horse race. Representatives from each Siena district participate in a bareback horse race dressed in their traditional colors by running laps around the square. 

But even if you’re going another time, there is plenty to stroll around the Piazza. Make sure to visit the Civic Museum in the Palazzo, and if you are brave enough, climb the 400 steps to the Torre di Mangia. The view over the city and its surroundings is worth it. 

After the Piazza, continue strolling through the narrow cobblestone streets, exiting the square. On your way to Cathedral square (the Duomo), you can find several small stores, but pay attention because the small entrances sometimes make them difficult to spot. 

That’s why you can almost always see the stores displaying wares on the street. Take the opportunity to practice your Italian and negotiate the price. That’s how I found leather hand-made mule shoes for a bargain. 

Source: Instagram

You can’t miss the Duomo, the Cathedral of Santa Maria Assunta.  This magnificent Italian romanesque church will amaze you not only for the architecture. You can tour inside and see the works by  Michelangelo and Donatello, among others. The tour also allows you to go to the top of the Cathedral and enjoy the view over Siena. 

(Source: Instagram)

At lunchtime, if you want to go where the locals go, you can try Particolare at Via Baldazzare Peruzzi. If you are on a budget, go to any trattoria away from the center. Ask for ribollita soup, a rich vegetable soup,  or the pici pasta—the Siena version of the Roman Cacio e Pepe—.

The next day, we went to explore the Tuscany coast. 

Livorno: The Tuscany Seaside 

Although Tuscany is famous for its green countryside, you can find enchanting seaside towns along the West Tuscany coast. One of them is Livorno. 

An ancient port, Livorno is still one of the busiest ports in Italy. It is famous for its seafood and incredible views. Although most people visit Livorno as a stop on their way to Pisa, it merits a day trip in its own right. 

Here is a short itinerary for a day visit: 

  • Enjoy the Ligurian sea by strolling by the Via Italia, which starts at the port and finishes at the Aurenza Harbor, a port with small fishing boats and fabulous coastal scenery. Along the way, several bars and restaurants offer tasty seafood. 
  • Don’t miss the Terrazza Mascagni.

Terraza Mascagni (Source: Instagram)

  • Visit the central market for a glimpse of fresh produce, fine seafood, and an opportunity to meet the Livornese. 
  • Explore the port, visit the 11th-century fort, Fortezza Vecchia, and enjoy the sea view and city from the Tower.

You can have no short experiences in Italy, from learning to cook, exploring their architecture, and immersing in art. Talking with local people is the best way to find the best places and activities. 

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