Discover Italy in Medieval Times: A Journey Through Ancient Secrets
Italy was a powerful country in medieval times and much from those days is still intact near Florence and Tuscany, hinting at the remnants of secrets left from the middle ages. Walking through these ancient lands today, you can still feel the echoes of medieval life in every stone and tower. From the towering fortresses that once protected wealthy families to the narrow cobblestone streets where merchants traded their precious silks and spices, Tuscany preserves its medieval heritage like a perfectly maintained history book.
Medieval Towns in Italy: An Intimate Tuscany Experience
Our private San Gimignano & Siena Tuscany Florence tour is the perfect Italian vacation destination for anyone enchanted by the rich history of that pivotal time in history.
A maximum of eight people will enjoy a wonderful guided day trip exploring medieval hill towns in the breathtaking Tuscan countryside. Our expert driver-guide will lead you through charming towns, showing you the elements that date back to medieval times and sharing stories and historical facts.
Want to unlock these medieval mysteries yourself? Our intimate Private Tuscany Tour from Florence lets you explore these ancient streets at your own pace, with a knowledgeable guide bringing centuries-old stories to life
Italy in the Middle Ages: From Roman Empire to Medieval Power
Travellers will learn how even after the decline of the Roman Empire, Italy was important in the world theatre because of its desirable geographic position. Medieval Italy saw the development and growth of some of the country’s most internationally renowned cities, such as Venice, which became extremely important to trade.
The rise of the Catholic Church and the power held by the Holy See were important aspects of politics domestically and internationally. The church was instrumental in education, being the place for learning as well as preserving classical culture. Monastic orders grew in numbers and were essential economically.
While most people associate Italy with the masters of Renaissance art, it was here during medieval times that artists began to rebel against Byzantine conventions for composition and their restrictive idea that all art should be religious. Artists began to create landscapes, still life paintings, and portraits of people in addition to Biblical scenes. It was during this time, by 1321, that Dante Alighieri finished writing his La Divina Commedia (The Divine Comedy) – considered one of the most important works in world literature.
While we envision peasants living in humble homes cobbled out of the earth around them, medieval Italy was being transformed. Construction began in larger cities like Tuscany—large civic buildings and cathedrals that reached to the heavens, along with the first Italian university in Bologna. During this exciting day trip, travellers will get to visit incredible medieval hill towns, including:
Siena: Medieval Italy's Perfect Time Capsule
An incredible Tuscan gem, Siena has done such a good job of preserving its medieval cityscape that its city centre was declared a World Heritage Site by the United Nations Educational, Scientific and Cultural Organisation (UNESCO). It is one of Italy’s most popular tourist destinations, with museums, villas, and an unbelievable shell-shaped town square called the Piazza del Campo noted for its impressive tower called Torre del Mangia. It is here that visitors come to watch the famous Palio horse race held annually in summer. For those seeking to truly immerse themselves in medieval Tuscany, our Private Siena and San Gimignano Day Trip from Florence offers an intimate journey through time. With just your group and our expert guide, you'll discover hidden corners and lesser-known stories that larger tours often miss.
San Gimignano: The Medieval Village Italy Never Forgot
While this medieval hill town is small, it offers an unforgettably impressive skyline with its well preserved tower houses. The walled town is built on a hilltop and these incredible examples of medieval architecture show examples of Romanesque and Gothic styles. These fortified structures belie the time of conflict here between families, who sought ways to defend themselves during the Guelph-Ghibelline conflict and struggled to survive the Black Plague. There are churches with frescos dating back to the middle ages here in the “Town of Fine Towers,” the centre of which is also a designated UNESCO World Heritage Site. Looking to escape the crowds and step back in time? Join our Private Siena and San Gimignano Day Trip from Florence, where you'll explore these medieval gems at your own pace, getting lost in narrow cobblestone streets while your guide shares tales of ancient family feuds and Renaissance intrigue.
Monteriggioni: A Medieval Village in Italy Frozen in Time
Perched atop a low-lying hill sits the walled town of Monteriggioni, which has stood sentinel over the area since about 1213 and was mentioned in Dante’s Divine Comedy. More remote than the other villages, Monteriggioni was built by the Sienese to defend their territory against the efforts of Florence to expand. Here you will see thick walls that have stood the test of attacking armies and time, still graced by 14 impressive square towers. There are narrow alleyways to explore as well as the charming main square, the Piazza Roma, and its Romanesque church.
Your Journey Through Medieval Castles in Italy and Historic Towns
From the moment you set foot in Tuscany, each stone, tower, and ancient wall tells a story of medieval grandeur. While our tour focuses on these three remarkable towns, they're just a glimpse of the medieval treasures scattered across the Italian countryside. Whether you're standing atop Monteriggioni's impressive walls, exploring San Gimignano's soaring towers, or wandering through Siena's winding streets, you'll experience how medieval castles in Italy evolved into thriving communities. Each fortress town offers a unique perspective on medieval life, from defensive architecture to daily commerce, from religious art to political intrigue. Although the small group San Gimignano & Siena tour only lasts eight hours, it will bring you back to beautiful Florence with memories to last a lifetime, and perhaps inspire you to explore more of Italy's magnificent medieval heritage, like with a Florence Walking Tour.
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