OF KNIGHTS AND NOBLEMEN

Take a trip back in time and explore two of central Italy’s most beguiling medieval towns, both recognised by UNESCO as World Heritage Sites.

Your expert guide will meet you in Siena and make sure no fascinating detail eludes you as you follow this stirring trail. No doubt you will notice the symbol of Siena, the she-wolf and twins, which links the town with its Roman origins, though centuries elapsed before this centre bloomed into the glorious gem you see today. Legend has it that Remus’ sons escaped to safety here after the murder of their father by the children’s uncle Romulus, the founder of Rome. Siena is indeed immersed in legends, steeped in ancient traditions and replete with true stories of battles and bravery. The town is also richly peppered with wondrously preserved monuments, churches and architectural marvels, attesting to its extraordinarily rich and riveting past.

Your guide will certainly show you around the 13th century Church of San Domenico, one of Siena’s best-loved landmarks, and explain why this site is intricately bound up with the life and miracles of beloved Saint Catherine. A collection of priceless works of art, including what is believed to be the only existing portrait of the saint, embellish the walls of the church but what draws thousands of visitors and pilgrims here is the much venerated relic of Saint Catherine’s holy head, carefully safeguarded in a chapel surrounded by master Sodoma’s frescoes.

Countless treasures await you inside the black-and-white striped Gothic Cathedral of Santa Maria Assunta: the wonderfully inlaid marble flooring, the rose window by Duccio di Buoninsegna, the marble pulpit by Nicola Pisano, Donatello’s statue of St. John the Baptist and the gorgeous Piccolomini Library. Well-known for its illustrated hymn books and beautifully preserved Renaissance paintings by Perugian painter Pinturicchio, the library was built at the request of Cardinal Francesco Piccolomini, Archbishop of Siena, to honour the memory and manuscript collection of his uncle Pope Pius II. A radiant fresco cycle depicts a glorified version of the life of the pope as well as mythological scenes and ornate decorative motifs, all rendered with the greatest skill and painstaking attention to detail.

No tour of Siena would be complete without exploring the shell-shaped Piazza Del Campo, for centuries the pulsing heart of the town’s social and political life and known the world over as the atmospheric setting of the Palio. Your guide will elucidate the origins of this famous horse race that still takes place regularly twice a year in July and August and help you understand why the event continues to play a significant role in fostering a Siennese sense of belonging, re-evoking the rivalry that flourished among its seventeen contrade and its legacy of ward-centric culture.

The looming Torre del Mangia, the elegant red-brick buildings and the medieval aura of the city’s winding alleys are among the unforgettable impressions to be savoured in this delightful wellspring of wonders.

After some free time for lunch, a 50-minute drive through the lovely Tuscan countryside brings you to the charming walled town of San Gimignano. Set high atop a hill, it looks out over silver green olive groves and lush vineyards in the Val d’Elsa below. Folktales claim the town was founded in 63 BC when two patrician brothers, Muzio and Silvio, fled Rome for Tuscany after their incrimination in the conspiracy of Catiline and built two castles on this very site. We know, however, that San Gimignano has been inhabited since Etruscan times but it was only much later, during the Middle Ages, that the town thrived due to its location along the Via Francigena, the pilgrimage route that linked Rome to Canterbury.

Here you can saunter through the two central squares, Piazza della Cisterna and Piazza del Duomo, wander along enchanting narrow streets and gaze up at a number of sturdy medieval towers that still dominate the skyline, pronouncing the wealth and ambitions of the families who built them centuries ago. Several outstanding Renaissance masterpieces can be admired here in their original locations, including Benozzo Gozzoli’s celebrated decorative fresco cycle of St. Augustine, located in a chapel of the Church of Sant’Agostino. Don’t forget to take a peek inside the Collegiata di Santa Maria Assunta, the city’s cathedral. Behind its bare Romanesque facade, this church conceals a precious Last Judgement by Taddeo di Bartolo, Benozzo Gozzoli’s Martyrdom of Saint Sebastian and Ghirlandaio’s fresco cycle depicting the legendary Life and miracles of Santa Fina who spent all her days lying on a wooden pallet deep in prayer.

While you weave your way through this remarkably beautiful town, pause for a moment to breathe in traces of a feudal air that still linger here. It only takes a tiny step of the imagination to picture the scene – not so very different from today – as it appeared to the nobles, knights and dames who must have taken this same route hundreds of years ago.

But San Gimignano also boasts some modern delights… before returning to Florence you might want to taste the local Vernaccia wine or savour the much acclaimed, award-winning ice cream lovingly created by Gelateria Dondoli.