Beyond Florence: Six Day Trips into Tuscany’s Hidden Gems

Florence (Photo: Envato)

 

Around cities like Rome, Florence, Venice, and many others in Italy, there are places that tourists—especially those from abroad—often don’t know about, or may have only vaguely heard of, without ever actually visiting them.

 

A trip to these destinations is truly worthwhile and offers the chance to explore magical places just a short distance from the cities where you're staying—all in the span of a single day.

This is the second in a series of "suggestions" for day trips or, if you prefer, explorations to take from these iconic cities.

 

Important: Please note that the destinations mentioned in the "Day Trips" series do not have kosher restaurants or shops. Therefore, you will need to purchase any necessary food from kosher establishments in Florence. Florence offers several kosher shops, a butcher, and both meat and dairy kosher restaurants.

Scenic view of Florence from Fiesole (Photo: Envato)

Travel time from Florence: 20-30 minutes by car

 

Just a few bends in the road beyond Florence, and suddenly the noise softens, the light changes, and you’re in Fiesole—a quiet hilltop town that’s been watching over Florence for more than two thousand years.

 

This is where the Etruscans settled long before the Romans thought of empire. You’ll find their traces still—an ancient amphitheater, the remains of a temple, mossy stones bearing the weight of time. But it’s the view that steals your breath: from the monastery at San Francesco, Florence looks like a dream floating in the Arno Valley.

 

Fiesole is less about sightseeing and more about slowing down. Have a spritz on a terrace as golden light spills across the rooftops. Or wander through the convent where Leonardo da Vinci once launched his flying experiments. Yes—here, where the air is light and ideas took flight, quite literally.

Vinci (Photo by Glorious 93, CC BY-SA 4.0, via Wikimedia Commons)

Travel time from Florence: Around 45 minutes by car

 

You’ve heard of Leonardo da Vinci. But have you ever walked the hills he knew as a boy? Vinci, the humble town of his birth, is wrapped in the same olive groves and quiet hills that may have inspired his first sketches and inventions.

 

This isn't a town of grand cathedrals or piazzas—it’s a place that breathes curiosity. The Museo Leonardiano, spread across a few small buildings, brings his machines to life. A bicycle prototype, a war machine, fantastical wings—all modeled from his drawings. And then, a short walk through the countryside brings you to Casa Natale, Leonardo’s farmhouse birthplace, where the silence is almost reverent.

 

If you’re lucky enough to come during one of the local festivals, you’ll see townsfolk dressed in Renaissance garb, paying homage to their most brilliant son. Vinci isn’t flashy. It’s thoughtful. Just like Leonardo.

Prato del Duomo hilltop landmark and countryside around San Miniato (Photo: Envato)

 

Halfway between Florence and Pisa, perched on three hills and cloaked in cypress, lies San Miniato, a town that smells—deliciously—of truffles. Especially in autumn, when the white truffle reigns supreme, this town becomes a celebration of earth’s finest aromas.

 

But San Miniato is more than its cuisine. Its history is tangled with emperors and popes—Frederick II built the great tower that still watches over the valley, and Napoleon once passed through, leaving a few legends behind.

 

The streets are steep and cinematic. One minute you're strolling past a noble palazzo, the next you're peeking into a hidden chapel. And every path seems to lead to a panoramic terrace where Tuscany rolls out below you like a painting.

 

Come for the views, stay for the stories—and the golden light that touches everything.

Piazza del Duomo in Pistoia (Photo: Envato)

 

Ask most travelers about Pistoia, and they’ll blink. And yet, walk into Piazza del Duomo and you’ll wonder how this place ever stayed under the radar.

 

Pistoia is a city of quiet dignity. Its cathedral is flanked by a striped marble baptistery that rivals Florence’s. The town’s underground tours reveal centuries of secrets, from plague hospitals to hidden aqueducts. And its Ospedale del Ceppo is adorned with a vibrant ceramic frieze that tells the story of charity in glowing Renaissance colors.

 

But what really defines Pistoia is its local rhythm—old men playing cards in tucked-away piazzas, artisans still working by hand, and trattorias serving rustic meals that taste like home.

Don’t come here looking for spectacle. Come for intimacy.

Bagno Vignoni (Photo: Envato)

Travel time from Florence: 2 hours

 

Imagine a town so small, its heart is not a piazza—but a steaming thermal pool, bubbling gently all year round. Welcome to Bagno Vignoni, a dreamlike spa village in the Val d’Orcia that feels lifted from a fable.

 

Here, ancient Romans, mystics, and Medici princes all came to soak their ailments in healing waters. And you still can—though the pool in the main square is now a tranquil monument, modern spas nearby let you sink into the same warm springs.

 

There’s not much to “do” here, and that’s the point. You wander. You soak. You sip a glass of wine as the mists rise from the pool at twilight. And if you listen closely, you might hear the echo of Saint Catherine of Siena’s prayers, whispered somewhere between stone and steam.

Certaldo (Photo by Chensiyuan, CC BY-SA 4.0, via Wikimedia Commons)

Travel time from Florence: About an hour

 

From the moment you ride the little funicular up to Certaldo Alto, you feel like you’re stepping onto a stage—one where every alley, every brick, whispers a story. And rightly so. This is the birthplace of Giovanni Boccaccio, the brilliant, mischievous mind behind The Decameron that inspired Geoffry Chaucer’s Canterbury Tales.

 

His house still stands, now a small museum, and from its tower you can gaze over the same hills he described centuries ago. But the real magic of Certaldo is its atmosphere—all red brick and quiet corners, with laundry flapping between archways and locals chatting on doorsteps.

 

In July, it transforms into a surreal dreamscape during Mercantia, a street theater festival that brings fire dancers, puppeteers, and acrobats into every square. Even without the fanfare, though, Certaldo feels timeless. Like a story paused mid-sentence, waiting for you to walk in and turn the page.

 

Conclusion

 

While each of these destinations offers beauty, history, and an escape from the crowds of Florence, it's important to plan ahead. None of these towns currently have kosher food options, so be sure to bring provisions with you.

 

Need help planning? Check out our guide to kosher food in Florence for where to stock up before your day trip adventures.

 

Andrea Alcalay from La Tour I-Talya. LaTour I-Talya is a project established and managed by a team of Italian Jews working together with one of the largest and most prestigious Italian Tour Operators. LaTour I-Talya specializes in tour packages which  focus on the amazingly rich Jewish historical and cultural heritage found throughout Italy — and the many lesser-known gems that exist off the beaten tourist paths.