Top 5 Best Small Towns In Tuscany To Visit This Summer

Welcome to the magnificent Tuscany region, where you can explore the region’s rolling hills, beautiful scenery, and historic cities. There is no better time to start a memorable adventure through this Italian wonderland than as summer approaches.

While there are many places to stay, we encourage you to think about the amazing experience of staying in a villa during your trip to Tuscany. Villas Guide villas are tucked away in the stunning countryside, combining rustic beauty with cutting-edge conveniences and unparalleled isolation.

Imagine waking up to the calming sounds of nature, soaking up the warm Tuscan sun, and absorbing the rich culture and history that permeate every inch of this amazing region.


Nestled in the heart of the Tuscan countryside, Montepulciano welcomes visitors with its medieval charm and exquisite architecture. As you wander through its narrow streets, you’ll encounter splendid Renaissance palaces and ancient churches.

Don’t miss the opportunity to savour the local specialty, Vino Nobile wine, known for its rich flavour and deep red hue. If you have extra time, exploring the Palazzo Comunale is a must, offering panoramic views of the surrounding vineyards and valleys.

San Gimignano

San Gimignano is a true jewel of medieval architecture, captivating visitors with its distinctive skyline adorned with towering stone towers. Step into the historic centre, a UNESCO World Heritage Site, and be transported back in time.

Marvel at the well-preserved mediaeval structures and immerse yourself in the lively atmosphere of the Piazza della Cisterna. Indulge in the town’s renowned gelato and sample the local Vernaccia wine, adding an extra layer of delight to your visit. After exploring the town, return to one of the charming villas in Tuscany, where you can relax and enjoy the breathtaking views of the Tuscan countryside.

Tuscany’s villas provide an ideal base for further exploration of the region. From San Gimignano, you can embark on excursions to other Tuscan gems like Florence, Siena, and Pisa.


Perched high on a hill, Volterra holds the secrets of its Etruscan past within its ancient walls. Explore the remnants of this fascinating civilization at the Etruscan Museum and witness the grandeur of the Roman Theatre.

Volterra is also renowned for its artisans, particularly its alabaster craftsmanship. You can discover workshops where skilled artisans transform this beautiful stone into intricate sculptures and souvenirs, providing an insight into the town’s rich artistic heritage.


Step into the picturesque town of Pienza, a UNESCO World Heritage Site, and be enchanted by its Renaissance beauty. Designed as an ideal Renaissance city by Pope Pius II, the town exudes harmony and elegance.

Stroll along the charming streets lined with artisan shops, and don’t forget to sample the famous Pecorino cheese, which is a true culinary delight. Visit the Palazzo Piccolomini to marvel at its exquisite architecture and enjoy breathtaking views of the surrounding Val d’Orcia.


Nestled amidst the rolling hills of Tuscany, Certaldo awaits with its enchanting medieval upper town, Certaldo Alto. Walk through its cobblestone streets and admire the well-preserved buildings that hark back to the Middle Ages.

Certaldo is also closely tied to the celebrated Italian author, Giovanni Boccaccio. You can delve into his legacy by visiting the Boccaccesca Food and Wine Festival, where the town comes alive with delectable treats and vibrant festivities.

While Tuscany’s well-known cities have their allure, it is in the hidden gems, Montepulciano, San Gimignano, Volterra, Pienza, and Certaldo, where the true essence of this enchanting region unfolds. These small towns offer a glimpse into the past, showcasing captivating architecture, unique traditions, and culinary delights.

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