exploring siena & southern tuscany

• Discover fascinating sites far from the crowds, from atmospheric San Galgano Abbey to picturesque Pienza

• Admire outstanding Gothic and Renaissance art, including Piero della Francesca’s frescoes in Arezzo

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

• Enjoy the varied landscapes of southern Tuscany, on the untouched Maremma coast and at Iris Origo’s La Foce

• Encounter the Etruscans at Rusellae and Volterra

• Appreciate Siena’s distinctive identity, on a Palio-themed walking tour

• Travel with an expert, specialist local guide and art historian Freya Middleton

SATURDAY 10 OCTOBER 2026 – ARRIVAL (D)

The tour begins when we meet at 3.00pm at a location (TBC) inside Florence’s Santa Maria Novella railway station, to travel together by private coach to Siena. After checking in to our hotel, we enjoy welcome drinks with tour leader Freya Middleton and our tour manager, before dinner together in a local restaurant. Overnight Siena.

SUNDAY 11 OCTOBER - SIENA & THE MIDDLE AGES (B)

Siena was a powerhouse of central Italy in the Middle Ages, with a flourishing financial sector, a prominent position on the Via Francigena to Rome, a reasonable local interest in wool processing and a unique form of self-government. Before the devastating Black Death of 1348, its population was booming and proud new civic buildings – from the Palazzo Pubblico to a cathedral that would have been one of Europe’s largest – began to rise up on its distinctive skyline. We start the day with a talk by Freya, before commencing our exploration of these medieval monuments together. At the Palazzo Pubblico, we appreciate how medieval town councillors lived and worked – and the principles by which they ruled, exemplified in outstanding frescoes such as Simone Martini’s Madonna in Majesty and a wonderful portrait of Guidoriccio da Fogliano on horseback. (Note: at the time of publication, the Cycle of Good and Bad Government in the Sala della Pace is closed for a lengthy restoration. Should it re-open in time for our visit, it will be included.) After time to admire the elegant design of the Campo, the shell-shaped square around which Siena’s horses race twice a year in the Palio, there is lunch at leisure. Afterwards, we continue with Freya to the vast site of Siena’s cathedral. From sculptures by the Pisano workshop, Donatello and Michelangelo, to the superlative manuscripts and frescoes in the new ‘grotesque’ style in the Piccolomini Library, we survey Siena’s greatest achievements in art. In the Museo dell’Opera del Duomo, there is the opportunity to come face-to-face with Sienese masterworks, such as Duccio di Buoninsegna’s Madonna in Majesty, and works by the Lorenzetti family. The late afternoon and evening are at leisure. Overnight Siena.

MONDAY 12 OCTOBER - IN THE MAREMMA WITH THE ROMANS, WALK #1 (B, L)

Today we have the first of our guided walks, along the Tuscan coast. The Maremma region lies beyond the well-travelled Tuscan tourist trail, but its harbours and ports were of strategic interest to medieval Siena. Today, the scenery is among Tuscany’s most attractive, with ruined watch towers, sand beaches and pristine seas, and the perfume of the Mediterranean macchia or scrub. We take a loop walk in the Alberese area (6.5km, approx. 3 hours on a flat packed-sand path under pine trees) before continuing to a coastal restaurant for our welcome lunch. After lunch, we travel to nearby Grosseto to visit the intriguing site of Rusellae (present-day Roselle). While it is not as impressive as Italy’s best-known archaeological sites, our tour with a site guide gives us an indication of how Etruscan settlements were occupied by the Romans, with Etruscan tombs, a Roman amphitheatre and even simple floor mosaics unearthed here. We return to Siena for an evening at leisure. Overnight Siena.

TUESDAY 13 OCTOBER - RACES & THE RENAISSANCE IN SIENA (B)

One of the great attractions of spending time in Siena is discovering how proudly local it remains. From the local accent and dialect – thought by some language scholars to be Italy’s most ‘pure’ – to unique styles in art and, of course, the madness of the hyper-local Palio, Siena has preserved many of its traditions despite its political occupation by rival Florence in the sixteenth century. Today, we meet a local guide for a day focused on Siena’s unique culture, in the neighbourhood heartlands (or contrade) of the Palio. We visit the small chapels, meeting houses and museums of the fiercely proud neighbourhood organisations to which each native Sienese feels so strongly bound. After lunch at leisure, there is time to explore Siena independently. You might like to meet your tour leader for a visit of the Oratorio di San Bernardino, which shows how Sienese painting continued to develop long after the naturalism of the Florentine Renaissance took hold in the rest of Italy. Overnight Siena.

WEDNESDAY 14 OCTOBER - ART, WINE & LANDSCAPE, WALK #2 (B, L)

Tuscany has many small wine regions, and a number produce wines boasting Italy’s highest appellations. But when many of us think of Tuscany and wine, we think immediately of the Chianti region. With a wine-making tradition that can be documented as far back as the Middle Ages, and a prominent position for centuries as the frontier territory between the republics of Florence and Siena, in more recent decades the area has become popular with foreign residents. At one point, it even earned the nickname of “Chiantishire”! Today we get to know Chianti in the best way, taking a walk through its heritage-listed landscape (approx. 5.5km, 3 hours, with some gentle hills). Our walking guide introduces us to some local villages and to Chianti’s gastronomic traditions, before we arrive at a country restaurant for lunch together. Afterwards, we continue by private transfer to the Castello di Ama. Located on a hill in the Chianti Classico wine district, it is a medieval town-turned-winery. In addition to its highly regarded wines, the winery is known for its collection of contemporary art. There are works by Louise Bourgeois, Anish Kapoor, Michelangelo Pistoletto and Lee Ufan, several of which were created specifically for this site. After our tour, we return to Siena. Overnight Siena.

THURSDAY 15 OCTOBER - VOLTERRA & ROSSO FIORENTINO (B)

Today we travel from Siena to Volterra, a fascinating town with ancient origins. Founded before the eighth century BCE, Volterra was a significant Etruscan centre, and its Archaeology Museum is one of the most important Etruscan museums in Italy. In the Middle Ages, it dabbled in self-rule and Volterra’s tiny baptistery and toy-sized town hall give it as a result one of Tuscany’s most beautiful streetscapes. As we discover at the local art gallery, Volterra also preserves one of the Renaissance’s most significant artworks: Rosso Fiorentino’s Deposition, a dynamic, colourful, almost wild painting of the early sixteenth century. We return to Siena for an evening at leisure. Overnight Siena.

FRIDAY 16 OCTOBER - A RUINED ABBEY & THE VIA FRANCIGENA, WALK #3 (B, L)

One of the reasons for Siena’s medieval prominence was its strategic position on an Italian superhighway: the Via Francigena, or Frankish route. Every year, it carried medieval pilgrims from Canterbury to Rome, and in Italy was used to transport goods and merchants between major cities and towns. Today, not far from Siena and together with our walking guide, we too become pilgrims, taking a series of walks on the Via Francigena (taken together, approx. 2 hours and 6km in length) with short transfers by van at certain points. The tiny walled towns and fortified abbeys that we visit show the possible dangers and threats for medieval travellers. The focus of our day, however, is the atmospheric Abbey of San Galgano, a large Cistercian monastery constructed where a local hermit, Galgano Guidotti, had lived a life of saintly renunciation. From 1220, the abbey’s monks served as the Republic of Siena’s financial administrators, and the complex grew; today, it lies in Romantic ruins and is one of Tuscany’s most evocative sites. After a simple lunch, we visit the nearby Chapel of Montesiepi, where we discover the miracle of St Galgano’s sword in the stone, as well as frescoes by Ambrogio Lorenzetti. Returning to the hotel, there is a talk before an evening at leisure. Overnight Siena.

SATURDAY 17 OCTOBER - PIERO DELLA FRANCESCA & MONTE OLIVETO MAGGIORE (B)

Today we travel to Arezzo, a pleasant hillside town that has given birth to some of Tuscany’s greatest figures, from the poet Petrarch to artist and art historian Giorgio Vasari. It was also the filming location for much of Roberto Benigni’s Oscar-winning film Life is Beautiful. We begin with a visit to the Church of San Francesco, where the main chapel is decorated with the best-preserved frescoes of Piero della Francesca. Telling the Legend of the True Cross, the fresco cycle bears the hallmarks of Piero’s mature style, as a naturalistic treatment of light and shade, and strict visual perspective offer a sober backdrop for kings and queens, warriors and saints. Afterwards, we continue with a walking tour of Arezzo and enjoy lunch at leisure. In the afternoon, we return to Siena via the Abbey of Monte Oliveto Maggiore. Set in woods in the centre of southern Tuscany’s iconic Crete region, this large and self-sufficient monastery was the motherhouse for the Olivetan Order, founded in 1313 by a prominent jurist from Siena. It is still a functioning abbey, and we enjoy a visit to its quiet cloisters, with their colourful – and humorous –frescoes by Signorelli and Il Sodoma. Please note that entry to the abbey from the coach parking must be made on foot, descending and then returning via a short but steep hill. Returning to Siena, the evening is at leisure. Overnight Siena.

SUNDAY 18 OCTOBER - THE VAL D’ORCIA & IRIS ORIGO (B, L, LIGHT DINNER)

We spend the final full day of our tour in the beautiful Val d’Orcia, a UNESCO World Heritage-listed landscape of bare hills, medieval hill towns and thermal hot springs against the backdrop of Monte Amiata. In the morning, we call in at Bagno Vignoni for coffee and a stroll, admiring a pretty but tiny village entirely oriented around its distinctive “piazza”: a giant pool of thermal waters, whose health benefits were enjoyed by Tuscans from St Catherine of Siena to Lorenzo the Magnificent de’ Medici. We continue to Pienza, once the insignificant hilltop village of Corsignano, but transformed in the fifteenth century by local boy Aeneas Silvius Piccolomini, known to history as Pope Pius II. Designating it the site of a papal court, he induced his cardinals to construct small Renaissance palaces here and built himself a fine Renaissance palace and cathedral in miniature. Pienza is now the most perfect Renaissance toy town in Italy. It is also famous for its gastronomy, particularly a local cheese, and we enjoy a farewell lunch together. In the afternoon, we travel to nearby La Foce. Now a splendid garden designed by Cecil Pinsent for writer Iris Origo, it lies at the centre of an agricultural estate transformed by Iris and her agronomist husband. La Foce is the site of one of Tuscany’s most famous views: a winding road ascending a pine-covered hill. Returning to Siena, we discuss our tour experiences over wine and a light meal in a local restaurant. Overnight Siena.

MONDAY 19 OCTOBER - DEPARTURE (B)

We check out of our hotel this morning and travel together by private coach to Florence. The tour ends with the coach’s arrival at Florence’s Santa Maria Novella railway station, ca 11.30am. From the railway station, it is also an easy journey by tram to Florence airport at Peretola.

Hotel Athena 4*, Siena, 9 nights

https://www.hotelathena.com/en/

An elegant and well-serviced hotel, with a good location for our itinerary: within walking distance of Siena’s central historic sites, but with quick access to the roads out of town for our day trips.

A short walk uphill brings you to the university district, with its restaurants and supermarket.

We have selected Deluxe rooms for our stay, which are bright, feel spacious and average 23sqm in size.

The hotel has a restaurant, panoramic terrace and bar.

A hotel of a similar standard may be substituted.

• 9 nights’ accommodation in a 4* hotel

• All breakfasts and 6 lunches or dinners, and aperitivi, with drinks included

• All ground transport, guided tours and entrance fees to sites as mentioned in the itinerary, and tipping

• A transfer by private coach to and from Florence’s Santa Maria Novella railway station and our hotel in Siena, to commence and depart the tour

• Expertise and commentary of an Australian tour leader throughout

• Expertise and commentary of a professional walking guide on three walking excursions

A $1,500pp deposit is required at the time of booking to hold your place on tour.

We will invoice you for a second deposit of $1,500pp, due on 12 June 2026.

We will invoice you for final payment for the tour, due on 27 July 2026.

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