Ciao a tutti, I’m Luca. If you’ve ever stood in the middle of San Gimignano’s Piazza della Cisterna in the height of summer, you know the feeling: it’s beautiful, it’s iconic, but it’s also packed to the brim with selfie sticks and overpriced gelato. Don’t get me wrong, I love the ‘Manhattan of the Middle Ages’ as much as anyone, but my secret tip is that the real magic of Tuscany often lies just a few kilometers away, in the shadow of those famous towers - and for a truly immersive experience, be sure to explore the region’s wine country, as my colleague Alessandro recently explored in her article about A 2025 Wine Lover’s Grand Tour of Tuscany’s Hidden Gems.
While the crowds are queuing for the tower climb, I’m usually heading into the rolling hills of the Val d’Elsa or the Val d’Orcia to find the spots where the stone is just as old, the wine is better, and the only sound you hear is the wind whistling through a medieval gate. Most tourists never find these spots, but for those who want something different, these are the true heart of Tuscany.
Certaldo Alto: The Red-Brick Dream#
Just a short drive (or a fun funicular ride) from the modern town of Certaldo lies Certaldo Alto. Unlike most Tuscan towns built from gray limestone, Certaldo is a warm, glowing world of deep red brick. It’s the birthplace of Boccaccio, the author of the Decameron, and walking through its narrow streets feels like stepping into one of his stories.
The main street, Via Boccaccio, is wide and majestic, but the real secret is wandering into the smaller alleys that lead to the Palazzo Pretorio. Look closely at the walls of the palace—they are covered in the coats of arms of the various families who ruled here. My favorite moment is sitting in the small garden behind the palace; the view over the vineyards at sunset is pure poetry, without a single tour bus in sight.
Monteriggioni: The Crown in the Hills#
You might recognize the silhouette of Monteriggioni from afar—a perfect circle of walls with fourteen towers crowning a gentle hill. Dante Alighieri was so impressed by it that he compared its towers to giants in his Divine Comedy. Most people just stop for a photo from the highway, but staying for an evening stroll is a completely different experience.
Walk the ramparts at dusk. When the day-trippers leave, the tiny piazza inside the walls becomes the village living room. There’s a small church, a few artisan shops, and a feeling of absolute security within those ancient stones. If you want to feel like a medieval knight (without the heavy armor), this is the place.
Colle di Val d’Elsa: The City of Crystal#
Colle di Val d’Elsa is often overlooked because it’s a bit more “industrial” in its history—it’s the crystal glass capital of Italy. But the upper part of the town, Colle Alta, is a labyrinth of steep ramps, underground passages, and vertigo-inducing views.
Entering through the massive Porta Nuova, you’re greeted by a quiet elegance that feels incredibly authentic. It’s a town of tunnels and bridges. Make sure to find the Baluardo, a panoramic point that offers a 360-degree view of the valley. It’s the kind of place where the local bakery still smells of rosemary and sea salt, and the old men playing cards in the shade won’t even look up as you pass by.
Luca’s Tips for Discovering the Neighbors#
- Timing is Everything: Visit Certaldo Alto in July for Mercantia, one of Europe’s best street theater festivals. The whole village transforms into a stage.
- The Funicular: In Certaldo, park at the bottom and take the funicular up. It’s a short ride, but the reveal of the red-brick village as you ascend is worth every cent.
- Taste the Onions: Certaldo is famous for its sweet red onions (Cipolla di Certaldo). Try them in a jam with local pecorino cheese—it will change your life.
- Crystal Hunting: In Colle di Val d’Elsa, look for the small workshops where they still blow glass. It’s a dying art, and seeing it in person is mesmerizing.
Tuscany is more than its famous postcards. It’s a collection of stories etched into stone and brick, waiting for someone curious enough to leave the main road. If you’re looking for the ‘real’ Italy in 2025, stop following the guidebooks and start following the horizon. The best secrets are always just one more hill away. A presto!