Jan 10 - 24, 2022
15 days
$TBCper person, twin share (land content only). $TBC supplement for sole use of a hotel room.

Tour Leader

Dr Kathleen Olive
Jan 10 - 24, 2022

Tour Leader

Dr Kathleen Olive$TBCper person, twin share (land content only). $TBC supplement for sole use of a hotel room.
  • Tour Info
  • Itinerary
  • Tour Leader
  • Hotels
  • Inclusions


Travellers flock to the cities and towns of Tuscany to admire the world’s greatest concentration of medieval and Renaissance art, but rarely devote sufficient time to fully appreciate its technical brilliance and intellectual richness. Unpack your bags and enjoy longer stays in Pisa, Siena and Florence on this 15-day tour exploring the region’s economic and cultural flowering in the Middle Ages, and its rise to European super-power with the Medici. Tuscany’s simple, seasonal cuisine is at its best in winter, when there are also fewer visitors and the weather is generally mild.


  • World-class art in Florence’s Uffizi and Accademia, Siena’s Pinacoteca and Pisa’s spectacular Museo di San Matteo
  • Beautiful villages and atmospheric abbeys, from Lucca and San Gimignano to Pienza and Monte Oliveto Maggiore
  • Explore the careers of major Renaissance artists: Piero della Francesca in Arezzo, Masaccio in the Brancacci Chapel, Filippo Lippi in Prato
  • Elegant Siena: time to shop and enjoy the evening passeggiata over four nights
  • Savour Tuscany without the tourist hordes: winter cuisine, wine tastings in stunning contemporary settings, uncrowded museums

Itinerary Overview

Days 1–3: Explore Pisa. Day trip to Lucca.

Days 4–7: Visit Volterra and San Gimignano. Discover Siena’s art and architecture, the atmospheric abbey at Monte Oliveto Maggiore and the beauty of Renaissance Pienza.

Day 8: Investigate Piero della Francesca in Arezzo.

Days 9–11: Contemplate Florentine sculpture from the Middle Ages to Renaissance. Follow the rise of the Medici dynasty in San Lorenzo and San Marco. Enjoy a day trip to Prato.

Days 12–15: Admire world-class art in Florence’s Uffizi and explore Michelangelo’s masterpieces at the Accademia. Survey Fiesole’s Etruscan and Roman heritage. Enjoy Tuscany’s resurgence at a stunning contemporary winery.

Detailed Itinerary

Start & Finish

The tour begins at our hotel in Pisa and ends at our hotel in Florence. Qatar and Emirates offer suitable connections into and out of Pisa and Bologna from most Australian cities. Contact us for quotes and bookings.

Detailed Itinerary

Included meals are shown with the symbols B, L and D.

Monday 10 January: Arrival

Our tour begins in the afternoon, with a briefing in the hotel and an orientation stroll. There is a light dinner tonight near our hotel. Overnight Pisa (D)

Tuesday 11 January: The splendour of medieval Pisa

This morning we explore the cosmopolitan style of medieval Pisa, influenced by its eastern trade. After a talk in our hotel, we enjoy a guided tour of the spectacular Piazza dei Miracoli. After we explore the cathedral, baptistery and restored Camposanto frescoes, there is time to climb the Leaning Tower. Following lunch at leisure, we visit the Museo Nazionale di San Matteo, one of Italy’s finest museums of the Middle Ages with a superlative collection of painted crosses, and then walk to nearby Santa Maria della Spina, where the reliquary chapel is entirely covered in delicate Gothic and neo-Gothic tracery. Overnight Pisa (B)

Wednesday 12 January: Elegant Lucca

Today we make the short trip to Lucca. On our walking tour of this well-heeled town, we explore its fascinating history, from Roman origins to Romanesque churches, medieval streets and Renaissance walls. Lucca has excellent shops and, after our welcome lunch in a fine local restaurant, there is free time to browse before we return to Pisa. We have a talk in our hotel this evening. Overnight Pisa (B, L)

Thursday 13 January: Clans and commerce in Tuscany

Today we check out of our hotel and travel to Volterra, famous for its production of alabaster and for its stark Romanesque beauty. Its regional museum contains the startling Deposition altarpiece by Rosso Fiorentino. In the afternoon we explore San Gimignano, its towers symbolising the factional conflict that ravaged medieval Tuscany. We also admire beautiful frescoes here by masters such as Benozzo Gozzoli and Ghirlandaio. After checking in to our hotel in Siena, we enjoy dinner in a nearby restaurant. Overnight Siena (B, D)

Friday 14 January: Siena and the via Francigena

Siena’s medieval growth was due in large part to the banking and trade it carried out along the Via Francigena, the primary pilgrimage route from northern Europe to Rome. After a talk in the hotel we take a guided tour of Siena’s cathedral complex. In the cathedral and baptistery, we appreciate the development of sculpture in Siena, from the Middle Ages to Renaissance, while in the Museo dell’Opera and Ospedale della Scala, we admire Duccio’s grand Maestà and the organisation of the city’s pilgrim traffic. The afternoon is at leisure. Overnight Siena (B)

Saturday 15 January: Into southern Tuscany

Today we enjoy an excursion into southern Tuscany, where the bare hills have a dramatic beauty in winter. In Pienza, we see the reinvention of southern Tuscany in honour of Pope Pius II, who was born here and had the town redesigned in the 15th century according to Renaissance principles. There is time for lunch at leisure in this beautiful town, renowned for its pecorino cheese. In the afternoon, we tour the Abbey of Monte Oliveto Maggiore, still surrounded by forest and decorated by Sodoma with frescoes celebrating the everyday life of the monks. Overnight Siena (B)

Sunday 16 January: Public and private art in Siena

We begin the day with a visit to Siena’s Pinacoteca Nazionale, little-visited but with a magnificent survey collection of Sienese painting from the medieval masters to the 16th-century Mannerists. We then meet our local guide for a visit of the Palazzo Pubblico, the town hall that preserves Lorenzetti’s wonderful fresco cycle on Good and Bad Government, a textbook of medieval political theory, and Simone Martini’s courtly Maestà. The afternoon is at leisure, before an evening talk in our hotel. Overnight Siena (B)

Monday 17 January: Piero della Francesca in Arezzo

After checking out, we travel to Arezzo, a picturesque village that preserves the most complete cycle of paintings by Piero della Francesca. He revolutionised perspective and geometry (even publishing a treatise on the topic), and his crystalline style inspired painters such as Jeffrey Smart well into the present day. After admiring the Legend of the True Cross cycle in San Francesco, we continue to the cathedral, which preserves another work by Piero as well as a wonderful medieval reliquary altar carved from marble. After free time for lunch and to explore the pretty town, we make the short trip to Florence. There is an orientation stroll after check-in, followed by a group dinner. Overnight Florence (B, D)

Tuesday 18 January: Life in medieval Florence

Today we explore the art of medieval Florence in its context, looking at how art and architecture were used by those who commissioned them. We begin with a visit to Orsanmichele, where guild rivalry inspired a revolution in sculpture. There are more works by Donatello and Ghiberti, along with masterpieces by Michelangelo, at the Museo del Bargello, Florence’s sculpture museum. We visit the museum before free time for a late lunch. In the afternoon we enjoy a private visit to the terraces of the cathedral, for a panorama of Brunelleschi’s cupola, Giotto’s belltower and the baptistery. There is the option to continue to the Museo dell’Opera del Duomo. Schedules permitting, we enjoy an evening of classic music in one of the city’s historic venues. Overnight Florence (B)

Wednesday 19 January: Fiesole and the grand dukes

Fiesole started off as early Florence’s great rival, but it was subdued in the 12th century and became a satellite suburb of luxury villas and gardens, a characteristic that it preserves to this day. Yet Fiesole was a significant Etruscan and Roman town, and its Museo Archeologico and Roman theatre contain a fine collection of objects. After time for lunch in Fiesole, with its panoramic views, we return to the city to meet our local guide at the Accademia Gallery. Michelangelo’s David has been exhibited here since the 19th century and is the museum’s greatest attraction, demonstrating the master’s philosophical as well as technical approach to sculpture. The teaching aspect of the Accademia was instituted under the Medici dukes, and we explore their love for pietra dura (Florentine mosaic) at a nearby workshop. There is a talk in our hotel this evening. Overnight Florence (B)

Thursday 20 January: Art for the Medici

The Medici family rose to prominence in 14th-century Florence, making a humble beginning as moneychangers but eventually becoming one of Europe’s most powerful dynasties. This morning we take a walking tour of their finest contributions to the city. At the Museo di San Marco, a Dominican monastery that the Medici Brunelleschi-designed church of San Lorenzo, which they entirely renovated, we admire the tranquil beauty of Fra Angelico, one of Cosimo de’ Medici’s favourite artists and now the primary subject of this wonderful museum. At the Palazzo Medici-Riccardi, we explore Benozzo Gozzoli’s sumptuous frescoes of the Magi in the family’s private chapel. The afternoon is at leisure, although we meet in the evening for a talk. Overnight Florence (B)

Friday 21 January: Prato & the periphery

While the focus has long been on the glory of medieval Florence, the Arno river valley was one of medieval Europe’s most populous places and its towns made a fortune from textiles. We spend today exploring vibrant Prato, which came under Florence’s influence in the 14th century. It preserves its own unique charms, however, and is enjoying a renaissance of industry, education and tourism. We admire works by Donatello and Filippo Lippi in the cathedral, which has preserved a relic of the Virgin’s girdle since the Middle Ages, survey its medieval streetscapes, and visit the wonderful Museo del Tessuto, showcasing Prato’s long history as a textile production centre. There is the option to remain in Prato for dinner. Overnight Florence (B)

Saturday 22 January: Renaissance masterpieces

Painting in 15th-century Florence changed remarkably, with a renewed interest in classical proportions, human anatomy and emotions, and a chromatic brilliance. This new age is known as the Renaissance, and Masolino and Masaccio’s frescoes in the Brancacci Chapel are often thought to have ushered it in. We begin the morning here, followed by free time to explore nearby Santo Spirito and the Oltrarno district. After lunch at leisure, we meet for a visit to the Uffizi Gallery, one of the world’s most significant art collections and established by the Medici to showcase the development of the Tuscan Renaissance. It is usually quiet in the afternoon, allowing us to better appreciate works by Giotto, Botticelli, Titian, Caravaggio and countless others. We have a group dinner to discuss our impressions this evening. Overnight Florence (B, D)

Sunday 23 January: Enlightenment to modern

In the 17th century, Florence’s dukes ceased to be as important on the European stage and the great developments in painting and sculpture moved elsewhere. But the Medici maintained an active interest in the sciences and medicine, sponsoring the work of Galileo and developing vast collections of scientific instruments, models and maps. At the Museo Galileo Galilei, Florence’s science museum, our guide introduces us to the collection. We continue with a trip into the nearby Chianti hills, stopping at Piazzale Michelangelo for its sweeping views before continuing to the Antinori winery at Bargino. A spectacular example of what modernity looks like in Florence today, the contemporary building is partially enclosed by a hill and surrounded by the countryside. It is a testament to the combination of innovation, respect for traditions and confidence that have made Tuscany what it is. After we enjoy a farewell lunch overlooking the clipped vines, we return to Florence where the later afternoon is at leisure. Overnight Florence (B, L)

Monday 24 January: Departure

Our tour concludes this morning, after breakfast in our hotel. Departing group members have made individual arrangements for their onward travel: please check your documentation for more information.

Dr Kathleen Olive

A literary and cultural historian with a PhD from the University of Sydney, with particular expertise in Italy, Spain and Japan.

Dr Kathleen Olive is a literary and cultural historian with close to 15 years’ experience leading tours to Italy, Spain, France, Turkey, Japan and the United States. She has a strong personal interest in the visual arts, interior design, fashion history and contemporary fiction.

Kathleen holds a BA with first class Honours and a PhD, both from the Department of Italian Studies at the University of Sydney. For a number of years she worked as a lecturer at the University of Sydney and the University of Technology, Sydney, teaching Italian language, literature and history. Kathleen continues to teach, as a national lecturer for the Australian Decorative and Fine Arts Society (ADFAS), and in adult education courses in Sydney. In 2015, her edition of the Codex Rustici (a 15th-century commonplace book that Kathleen worked on with Nerida Newbigin, for her doctoral studies and for publication) was presented to Pope Francis on his first official visit to Florence.

Kathleen’s historical and artistic knowledge stretches from the Middle Ages through to the early 20th century. In Italy she has led numerous tours focusing on the medieval and Renaissance periods. In Spain she has a particular concentration on the “Convivencia” of Islamic, Christian and Jewish cultures in the south, and on the medieval pilgrimage routes of the north. Her tours of the USA’s north-east have focused on American collectors and their Gilded Age reinventions of European glory days, and in Japan she is particularly interested in contemporary design, from fashion to architecture. Kathleen speaks fluent Italian, is conversant in Spanish and understands French.

Kathleen was first involved on a tour to Italy in 2003 and it sparked her passion for on-the-spot communication of art and history. Since 2010 she has worked exclusively for Academy Travel, leading 6 tours a year. She has designed a number of our popular tours, from the Florence residential, to surveys of the courts of Renaissance Italy and of central Italy’s villas and gardens, as well as “twin city” tours to Palermo and Naples and to Florence and Rome. Closer to home, Kathleen is leading Academy Travel’s inaugural tour to Japan and our popular tours to Tasmania.

We asked Kathleen, what do you enjoy most about leading a group tour?

“I really enjoy travelling with groups who share interests in the history, culture and even food of a destination. It means that those personal connections are there right from the beginning, just waiting to be made.”

“There’s nothing I enjoy more than finding out the particular interests of my fellow travellers – an artist, a dish they love eating, their memories of a particular place – and finding a way to make an experience happen for them. That might mean recommending a particular wine bar, directing them to a museum that features artists they already like, or suggesting the best time of day for a view over a town. It’s so satisfying to be involved in making these kinds of memories for people.”

“Many of the people I travel with comment on my passion for the places I visit. It’s not just that I know my names and dates – it’s that I really enjoy bringing out the connections between history and art, for example, or between landscape and food. I never grow tired of injecting this kind of life into ‘dry’ academic knowledge.”

View Bio & Upcoming Tours


These 3 and 4-star hotels have been selected principally for their central location.

Pisa, Hotel Bologna (3 nights)

An elegant hotel in the historic centre of Pisa, a short walk to the main sights in Campo dei Miracoli. www.hotelbologna.pisa.it/en

Siena, NH Siena (4 nights)

Five minutes’ walk from Via di Banchi di Sopra, Siena’s elegant pedestrian thoroughfare, the hotel has well-appointed rooms and a restaurant. www.nh-hotels.com/hotel/nh-siena

Florence, Hotel Pensione Pendini (7 nights)

With an enviable position on Piazza della Repubblica, this impeccably restored hotel has well-sized rooms and a dedicated repeat clientele. www.hotelpendini.it

Tour Inclusions

What is included in the tour price? 

Unless otherwise stated in the itinerary, our tours include the following:

  • Any flights mentioned in the itinerary that take place during a tour
  • Land travel by private air-conditioned coach. Where appropriate, taxis or public transport are also used for short distance travel on some tours
  • All accommodation in hotels or apartments as stated in the itinerary
  • Breakfasts, lunches and dinners specifically stated as included in the itinerary
  • Drinks at welcome and farewell meals. Other meals may not have drinks included
  • Background talks on tour, site notes and online resources
  • Services of tour leader throughout tour
  • All entrance fees to sites mentioned in the itinerary
  • Local guides at some sites
  • Tips for drivers, local guides and restaurants for included meals
  • Costs involved in obtaining visas for countries visited, where required and when stated as included

Airport Transfers

Tours begin either at the arrival airport or the first hotel, depending on the itinerary. If you have booked your international flights with Academy Travel and arrive before the tour commences, we will provide airport to hotel transfers to the closest main city on your arrival, and to the closest airport at the end of the tour. These may be either individual or group transfers.

What is not included in the tour price?

Our tours do not include the following:

  • Return international/domestic air travel unless those flights take place during the tour
  • Special taxes and airport levies that can only be paid in cash at the destination. We will advise you of these charges (if any) before you depart
  • Travel insurance. We require all participants to have comprehensive travel insurance. A typical policy for one of our tours will cost from $160 upwards, depending on your age, pre-existing medical conditions, the countries you are visiting and the overall length of your trip
  • Lunches and dinners not specifically mentioned as included in the itinerary
  • Personal expenses such as laundry and phone calls
  • Costs associated with any activity mentioned as “optional” in the itinerary, or any suggested free time activity

Tour Details

Fitness Requirement

Grade Two

A Grade 2 tour is appropriate for travellers in good health with good mobility, who can comfortably participate in up to 3 hours of physical activity per day on most days.
More Details


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Speak to a consultant

For further information or to secure a place on this tour please contact:
Hannah Kleboe (02) 9235 0023 or 1800 639 699
(outside Sydney)

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