Tuscany is world-famous for its art cities, but it’s often the smaller and lesser-known villages that offer the most authentic experiences. Postcard-like landscapes, slow rhythms, genuine flavors, and breathtaking views: here are 5 must-visit Tuscan villages to explore with a private tour, away from the crowds and with the freedom to customize every stop.
1. Pienza – the Jewel of Val d’Orcia
A UNESCO World Heritage site and symbol of Tuscan Renaissance, Pienza is an architectural marvel nestled among the hills of Val d’Orcia. Walking through its quiet streets, you can admire the Cathedral, Palazzo Piccolomini, and breathtaking views of the surrounding countryside.
Why visit it with a private tour:
You can leisurely savor the famous Pecorino di Pienza, stop at the most beautiful viewpoints, and perhaps have lunch in an authentic trattoria overlooking the valley.
2. San Quirico d’Orcia – Elegance and Tranquility
Often overlooked in favor of more famous destinations, San Quirico d’Orcia preserves intact the charm of a refined medieval village, with Renaissance gardens, ancient churches, and mighty walls. It’s the perfect spot to breathe in the true essence of the quietest Tuscany.
Why visit it with a private tour:
The route between Pienza and San Quirico crosses the famous cypress road and rolling hills: with a local driver, you can stop wherever you want to take photos and enjoy the landscape at your own pace.
3. Cortona – Art, Spirituality, and Sunsets
Cortona is a natural terrace overlooking the Val di Chiana, famous for its Etruscan spirit and for being the setting of the book Under the Tuscan Sun. Besides the Cathedral and museums, it offers panoramic corners and a lively local atmosphere.
Why visit it with a private tour:
It allows you to comfortably reach the historic center without stress, with the possibility of combining the visit with a food and wine tour in the surroundings.
4. Montefioralle – the Fairy-Tale Village in the Heart of Chianti
Just a few minutes from Greve in Chianti, Montefioralle is one of the smallest and most enchanting villages in the region. Stone houses, flowery alleys, and absolute silence: it seems to have come straight out of a postcard.
Why visit it with a private tour:
Being off the main routes, it’s perfect for an authentic stop during a wine tour in Chianti, between one winery and another.
5. Castiglione Della Pescaia – Sea and History
Not just hills: the Tuscan coast also holds small gems. Castiglione della Pescaia combines a medieval atmosphere with a relaxed seafront. The perched historic center is perfect for a panoramic walk overlooking the Tyrrhenian Sea.
Why visit it with a private tour:
With a dedicated driver, you can combine the visit with a day of relaxation by the sea, or with a food and wine stop in the Maremma countryside.
Why Discover the Villages with a Private Tour?
Visiting these villages with a tailor-made excursion allows you to:
- avoid standard tourist routes
- manage your time flexibly
- rely on those who know the territory well
- add local experiences such as tastings, visits to oil mills or wineries
- experience Tuscany in an authentic and relaxed way
Conclusion
Whether you’re a photography enthusiast, a food lover, or simply looking for quiet and authentic corners, these villages will offer you unique experiences.
With Tuscany Excursions, you can create a personalized itinerary and let expert local drivers guide you to discover a more intimate, genuine, and unforgettable Tuscany.