7 Hidden Gems of Tuscany You Need to Discover
If you’ve already explored Florence, Siena, and Pisa, it’s time to discover Tuscany’s hidden gems. Beyond the iconic landmarks and tourist hotspots lie charming villages and lesser-known towns that preserve authentic Tuscan culture, spectacular views, and delicious culinary traditions.
These seven hidden gems showcase the authentic spirit of Tuscany, where you will find history, beauty, and tradition
But without further ado, let’s start with Monteriggioni.
Monteriggioni: Perfect Medieval Fortress
Highlights:
- Circular walled town with 14 perfectly preserved towers
- Walkable fortress walls offering panoramic views of the Chianti countryside
- Piazza Roma, the charming central square with the Church of Santa Maria Assunta
Monteriggioni stands as one of Italy’s most impressive medieval walled towns. This perfect circular fortress, built by the Sienese between 1213 and 1219, appears so striking from a distance that Dante mentioned it in his Divine Comedy, comparing its crown-like ring of towers to giants encircling the infernal abyss.
Walking through the single main street of this tiny hamlet feels like stepping back in time. The imposing walls, measuring approximately 570 meters in circumference and punctuated by 14 rectangular towers, have remained largely unchanged for eight centuries. For a modest fee, you can climb onto the walls and walk a section of the ramparts, enjoying breathtaking views of the undulating Chianti countryside.
The heart of Monteriggioni is its main square, Piazza Roma, dominated by the simple Church of Santa Maria Assunta. In summer, the town comes alive during the medieval festival “Monteriggioni Festa Medievale” when locals wear period costumes, and the streets fill with musicians and flag throwers.
Transportation
You can reach these 7 hidden gems of Tuscany using public transportation. It must be said, however, that the local buses are not as frequent, sometimes only once or twice a day. Delays are also an issue. At the moment, there is no app to actually trace the buses, which makes the whole experience rather unpredictable.
Personally, I suggest renting a car in Tuscany; that’s the best way to explore this magical region. My suggested website to rent a car is DiscoverCars, basically an Airbnb of cars that ranks all providers based on the users’ feedback. I usually filter between 8 and 10 stars to have the most trusted rentals and go for the most economical price.
San Quirico d’Orcia: Quintessential Tuscan Landscapes
Highlights:
- Medieval Collegiate Church with its magnificent portal carvings
- Horti Leonini, perfectly preserved Renaissance gardens
- Iconic cypress-lined roads and rolling hills of the Val d’Orcia
San Quirico d’Orcia sits at the heart of the UNESCO-protected Val d’Orcia, where gentle hills, cypress-lined roads, and golden fields create the quintessential Tuscan landscapes that have captivated painters and photographers for centuries.
This walled medieval town rewards visitors with its splendid Collegiate Church, adorned with ornate portals that showcase exquisite Romanesque and Gothic stone carvings. The 15th-century Horti Leonini Gardens offer a serene retreat with their geometrical Italian-style design and ancient roses. At the garden’s highest point stands a monument to Garibaldi, providing picture-perfect views over the terracotta rooftops and the surrounding countryside.
Just outside town lie two of Tuscany’s most photographed scenes: the Chapel of Vitaleta, a tiny isolated chapel perched on a hilltop, and the famous cypress-lined road that snakes up to Pienza. Dawn and dusk transform these landscapes with golden light, creating scenes that highlight, once again, the timeless beauty of rural Tuscany.
Sorano: Etruscan Marvel on the Cliffside
Highlights:
- Dramatic medieval town dramatically carved into tuff rock
- Orsini Fortress and its fascinating underground passages
- Vie Cave, ancient sunken Etruscan roads cut deep into the rock
Often overshadowed by its neighbour Pitigliano, Sorano offers equal drama with fewer crowds. This medieval town seems to emerge directly from the tuff rock cliff face, with houses stacked precariously atop one another, creating a vertiginous labyrinth of narrow streets, steep staircases, and hidden passageways.
The massive Orsini Fortress dominates the town, its imposing structure a testament to medieval military engineering. Tour the fortress to discover its network of underground tunnels and enjoy sweeping views of the surrounding Maremma countryside from its battlements.
What makes Sorano truly special is its Etruscan heritage. The surrounding area is crisscrossed by “Vie cave”, mysterious sunken roads carved up to 20 feet deep into the soft tuff rock by the Etruscans. These ancient pathways, shrouded in moss and ferns, create an atmospheric hiking experience that connects you directly to a civilisation that flourished here 2,500 years ago.
Pitigliano: The Little Jerusalem of Tuscany
Highlights:
- Striking panoramic views of the medieval town built atop volcanic tufa rock
- Jewish quarter with its restored synagogue and underground wine cellars
- Network of Etruscan pathways carved into the tufa rock surrounding the town
Emerging dramatically from volcanic tufa rock, Pitigliano creates an unforgettable first impression. The medieval town seems to grow organically from the cliff face, with houses perched precariously on the edge, creating a picture-perfect scene that belongs on a postcard.
What makes Pitigliano particularly fascinating is its Jewish heritage. Once home to a thriving Jewish community, the town earned the nickname “Little Jerusalem“. Explore the restored synagogue and museum in the former Jewish quarter, where you’ll learn about the coexistence of different cultures throughout Pitigliano’s history.
Don’t miss exploring the surrounding countryside, where Etruscan “Vie cave” (excavated roads) cut deep into the tufa rock. These ancient pathways, some up to 20 feet deep, create a mystical hiking experience through a landscape that feels untouched by time. The town’s Palazzo Orsini houses an archaeological museum showcasing Etruscan artifacts found in the area, providing context to the ancient civilisation that once dominated this region.
I still remember my first time in Pitigliano. I drove from Rome. Actually, this town is closer to Rome than Florence by car. I would not believe the view from the main road. And I still can’t understand how the houses on the edge of the cliff are still there, after so many centuries.
Montemerano: Medieval Gem with Artistic Treasures
Highlights:
- Perfectly preserved medieval stone village with concentric circular layout
- Church of San Giorgio with its remarkable collection of Renaissance art
- Enchanting Piazza del Castello, one of Tuscany’s most romantic squares
Montemerano remains one of Tuscany’s best-kept secrets. This tiny stone village with its concentric circles of narrow lanes feels like a medieval time capsule, entirely untouched by modern development. The stone houses, adorned with flowering plants cascading from window boxes, create an atmosphere of timeless beauty.
The village’s unassuming Church of San Giorgio holds an unexpected treasure: a remarkable collection of Renaissance paintings known as the “Montemerano Polyptych“. This artistic wealth in such a small community attests to the historical importance of this settlement.
Piazza del Castello forms the heart of the village, an intimate stone square surrounded by ancient buildings where time seems to stand still. As evening falls, the warm glow of streetlamps creates a magical atmosphere. Just a short drive from Montemerano, the famous Saturnia hot springs offer a rejuvenating dip in therapeutic thermal waters that have been enjoyed since Etruscan times.
Cetona: Elegant Living in the Shadow of a Volcano
Highlights:
- Bronze Age settlement at Belverde Archaeological Park
- Elegant Piazza Garibaldi with its Renaissance buildings and the Church of San Michele Arcangelo
- Mount Cetona views and the surrounding olive groves and vineyards
Beneath the extinct volcano of Mount Cetona lies the elegant stone village of the same name. This sophisticated hamlet, beloved by artists and writers seeking inspiration, centres around the beautiful Piazza Garibaldi, where locals gather at outdoor cafés beneath stone arcades.
The town’s historical significance extends back to prehistoric times, as evidenced by the fascinating Belverde Archaeological Park and the Civic Museum of the Prehistory of Mount Cetona. These sites showcase artifacts from Bronze Age settlements discovered in the caves on the mountain’s slopes, offering a glimpse into humanity’s ancient past.
Cetona’s charm lies in its understated elegance. Wander through the concentric circles of streets that spiral up to the 10th-century fortress at the summit, discovering artisan workshops, specialty food stores, and magnificent noble palaces along the way. The surrounding countryside, dotted with cypress trees, olive groves, and vineyards, creates the perfect setting for this refined Tuscan gem.
On my last trip, I was even able to find amazing chestnuts in the forest around town that matched perfectly the local red wine, of course
Anghiari: Medieval Masterpiece on the Battleground
Highlights:
- Dramatically positioned medieval town perched on a steep hillside
- Narrow, winding streets lined with beautifully preserved stone buildings
- Historic battlefield where the famous Battle of Anghiari took place in 1440
Perched dramatically atop a hill overlooking the Tiber Valley, Anghiari’s strategic position made it the site of the famous Battle of Anghiari in 1440, immortalised in a now-lost Leonardo da Vinci fresco. Today, this fortified town’s perfectly preserved medieval centre, with its maze of narrow alleys, steep staircases, and ancient arches, makes it one of eastern Tuscany’s most interesting destinations.
Walking through Anghiari’s historic centre reveals architectural treasures at every turn. The imposing 13th-century town walls, the Palazzo Pretorio with its collection of coats of arms, and the Palazzo Taglieschi, housing the State Museum with its impressive collection of Renaissance art, all speak to the town’s historical importance.
Anghiari is known for its skilled artisans, particularly woodworkers, weavers, and ironworkers who maintain centuries-old traditions. The town hosts a vibrant antiques market on the second Sunday of each month, drawing collectors from across Italy. For spectacular views, walk along the medieval walls that offer panoramic vistas of the valley that witnessed one of Renaissance Italy’s most significant battles.
An interesting thing is that Anghiari si positioned next to where the Tiber River starts its way down to the Mediterranean Sea, going through the beautiful city of Rome.
