exploring siena & southern tuscany

october 2026
freya middleton

*** Preliminary Itinerary ***

Discover centuries of art and history in Siena and southern Tuscany’s quiet centres, while enjoying gentle guided walks through landscapes of outstanding beauty and significance

OVERVIEW

In the thirteenth and fourteenth centuries, Siena was one of the most prominent cities in Western Europe, with thriving local industries, financial networks that encompassed popes and kings, and a local artistic culture that ensured an enduring legacy of luxurious and taste-making Gothic art. Its influence spread far beyond its city walls, to the wild Maremma coast with its Etruscan ruins and Cistercian abbeys, as well as closer to home, in the gentle hills of Chianti that would become the centre of a prestigious modern wine region.

This 10-day tour takes an in-depth look at this extraordinary history and heritage, from a comfortable base in Siena. A carefully designed program of talks, excursions and guided walks allows for an active exploration of archaeological sites, outstanding Gothic and Renaissance art and architecture, and celebrated food and wine – all in locations of great natural beauty.

The tour is enhanced by the expertise of your tour leader Freya Middleton, a well-known Australian art historian and qualified local guide who has lived in Tuscany for over twenty years.

TOUR LEADER

Freya Middleton is an Australian art historian and guide who has lived in Tuscany for over twenty years.

Freya has a Bachelor of Arts from the University of Sydney, with a major in Art History, and a Masters in Renaissance Studies from Warwick University. She undertook in-country study in Florence and interned at The Peggy Guggenheim Collection in Venice.

Freya is the founder and principal of Freya’s Florence, a travel agency that brings together expert guides specialising in the art, history and culture of Florence and Tuscany. A passionate communicator of her knowledge of and passion for all things Italian, she speaks fluent Italian and French.

Highlights

  • Discover fascinating cultural sites far from the tourist crowds, from the atmospheric ruins of San Galgano abbey to picturesque Pienza

  • Admire outstanding Gothic and Renaissance art, including Siena’s Cycle of Good and Bad Government and Piero della Francesca in Arezzo

  • Survey the rolling hills of Chianti on a guided walk, tasting storied wines and visiting a contemporary art site

  • Enjoy the varied landscapes of southern Tuscany, from the untouched Maremma coast to Iris Origo’s La Foce garden in the UNESCO-listed Val d’Orcia

  • Encounter the Etruscans, from the archaeological site at Rusellae to the world-class Etruscan Museum in Volterra

  • Appreciate the proud and distinctive identity of Siena, on a Palio-themed walking tour and with select gastronomic experiences

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