Tuscany’s rolling green hills, sun-soaked vineyards, and cobblestone streets have captured the hearts of travelers for centuries. Most visitors flock to the iconic destinations—Florence’s art-filled streets, Siena’s historic charm, Pisa’s famous leaning tower, and the picturesque beauty of Chianti and Pienza.
But beyond these renowned locations lies a different side of Tuscany—quieter, more intimate, and equally captivating. Tucked away from the crowds, the region is sprinkled with enchanting hidden villages brimming with character, stunning views, and unforgettable cuisine. These little gems offer a more personal connection to Tuscany’s authenticity and a slower pace to soak it all in. If you're a traveler with a passion for off-the-beaten-path adventures, I think you'll find that these five hidden gem villages in Tuscany deserve a spot on your itinerary. I love them all!
1. Monteriggioni – A Medieval Jewel Near Siena
Nestled just a short drive from Siena, Monteriggioni is a jewel of medieval architecture that feels like stepping back in time. Encircled by ancient walls that date back to the 13th century, this village is a living, breathing piece of history.
Begin your exploration by walking the castle walls for panoramic views of Tuscany’s sweeping countryside. Inside the village, cobblestone streets lead to charming little shops, cafes, and artisan boutiques selling handmade goods.
The heart of Monteriggioni is its piazza, a quaint square surrounded by historic buildings. Grab a table at a local café, indulge in a glass of Chianti wine, and savor the tranquility. Monteriggioni’s manageable size makes it a joy to explore on foot, with every turn revealing more charm and history.
Insider tip: Visit during the Monteriggioni Medieval Festival (held annually in July) to experience lively reenactments, music, and period costumes.
2. Montecatini Alto – Panoramic Beauty and Laid-Back Elegance
Perched high on a hill just an hour from Florence, Montecatini Alto is a hidden delight that charms its visitors with breathtaking views and a sense of timeless relaxation. The historic funicular ride to the village is an experience in itself, offering a nostalgic mode of transport with stunning scenery along the way.
Once you arrive, you'll be greeted by narrow, flower-draped alleyways, delightful piazzas, and an array of excellent restaurants. Sit down for a leisurely meal and enjoy the local specialties while taking in the jaw-dropping vistas. Montecatini Alto has an undeniable air of sophistication but remains welcoming and easygoing.
Insider tip: Make sure to visit in the late afternoon or early evening to enjoy a golden hour that sets the hillside and village aglow.
3. Peccioli – Ancient Charm Meets Contemporary Art
Peccioli, a small village nestled between Pisa and Volterra, surprises visitors with its seamless blend of ancient architecture and contemporary flair. Walking through the village, you'll find stunning views over vineyards and olive groves at every turn, but it’s the modern art installations scattered throughout that make Peccioli truly unique.
This marriage of the old and the new reflects the creative spirit of the community. The village’s narrow streets invite you to slow down and notice the details—whether it's the intricate stone facades or a bold piece of modern sculpture standing proudly on a centuries-old corner.
Sometimes, we even stop here on one of our private food& wine tours!
4. Montecarlo – Tuscany’s Hidden Wine Paradise
No, I'm not talking about the famous Monte Carlo on the French Riviera... I mean the village of Montecarlo, located near the charming city of Lucca! This tiny Tuscan village is a haven for wine lovers and food enthusiasts.
Surrounded by vineyards that produce some of the region’s finest wines, Montecarlo is famous for its impeccable wineries and traditional meals. Whether you prefer a robust red or a crisp white, the wines produced here are exquisite. Pair them with Montecarlo’s spectacular olive oil and fresh, local dishes for an unforgettable culinary experience.
While you’re here, take a stroll through the peaceful streets and soak in the local ambiance. Montecarlo might be small, but it’s packed with charm, making it a perfect addition to your Tuscan adventure.
Insider tip: Visit one of the wineries here, to learn more about the regional food and wine!
Pitigliano
Carved directly into the golden-hued tuff rock, Pitigliano is an ancient and enchanting borgo nestled in the Maremma region of southern Tuscany. This breathtaking village, often referred to as "Little Jerusalem" due to its rich historical ties to a once-thriving Jewish community, exudes an air of mystery and timeless beauty. As you wander its winding alleys and admire the dramatic cliffside views, you’ll be immersed in a unique tapestry of history and nature.
Insider tip: Don’t miss the opportunity to visit the nearby Saturnia thermal springs, where you can relax in the naturally warm, cascading waters — the perfect complement to your exploration of this magical village.
Discover the Best of Tuscany, with the Right Guidebook (Written by a Local with 20 Years of Experience!)
Tuscany is iconic for a reason, but the lesser-known corners of this breathtaking region are equally deserving of admiration. From Monteriggioni’s medieval charm to Montecarlo’s wine-soaked indulgence, these hidden villages offer an authentic side of Tuscany that’s far from the tourist crowds.
For even more insider recommendations, exclusive tips, and detailed venue guides, check out Tuscany for the Shameless Hedonist 2025—available now on Amazon. It’s your ultimate companion for uncovering the heart of Tuscany and designing a trip unlike any other.
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