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Siena at Christmas - Art and architecture in Southern Tuscany

The splendid architecture, enchanting streetscape and wonderful works of art of Tuscany’s finest historic cities.

Stay throughout in a five-star hotel in Siena, finest of Italy’s hilltop towns.

Day trips through beautiful countryside to Arezzo, Pienza and San Gimignano.

Major medieval and Early Renaissance frescoes and panel paintings, as well as other arts.

  • Siena, Cathedral, watercolour by W.W. Collins, publ. 1911.
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Spilling across three converging hilltops, Siena contains the most extensive and beautifully preserved medieval townscape in Europe. The Queen of Tuscany reached the apogee of her power, wealth and creativity in the High Middle Ages when she was an independent republic. Her great public buildings were constructed during this period: the splendid town hall and extraordinarily ambitious cathedral built to rival Florence. 

There is plenty of excellent Renaissance art here, but it is medieval painting for which the city is best known. The Sienese school reached its pinnacle of refinement before the Black Death in 1348, though great works continued to be produced for the next century and a half. A host of brilliant artists led by Duccio, Simone Martini and the Lorenzetti brothers created a distinctive style of exquisite delicacy – of design, detail and colour – and images which are numinous yet naturalistic.

Long before Siena lost its political independence to Florence in 1555, Florentine and other Tuscan artists had made their impact here, including Giovanni Pisano at the cathedral and Donatello in his bronze sculptures for the baptistery. But Sienese art long preserved its distinctive character and had an enduring influence on cities in the rest of central Italy.

The tour ranges through beautiful landscapes to present many of the finest works of art in southern Tuscany to other little historic cities. Pienza: the first ideal town of the Renaissance, with quattrocento façades and gilt Sienese altarpieces in the cathedral. San Gimignano: hilltop town with a unique cluster of medieval towers and equally spectacular 14th- and 15th-century frescoes. Arezzo: location of the Legend of the True Cross by Piero della Francesca, most beguiling and enigmatic of early Renaissance painters. 

Day 1

San Miniato, Siena. Fly c. 11.25am from London City to Florence. Drive to San Miniato, whose strategic location straddling the Via Francigena and the route between Pisa and Florence made it one of the most important imperial centres in Tuscany in the 12th and 13th centuries. Continue to Siena, where all six nights are spent.

Day 2

Siena. Our exploration of this hilltop city begins with the cathedral museum to see Duccio’s Maestà, the greatest of all medieval altarpieces. The 14th-century Palazzo Pubblico, a fortress of delicate design, contains frescoes by Simone Martini and the Lorenzetti brothers. Finally, the cathedral, an imposing Romanesque and Gothic construction of white and green marble with outstanding Renaissance sculpture and painting including Pinturicchio’s brilliant frescoes and the font by Ghiberti, Donatello and Jacopo della Quercia.

Day 3

Pienza, Siena. Created by Pope Pius II as a tribute to his birthplace, the central square of Pienza is a jewel of Renaissance architecture and planning. The Museo Diocesano, in a palace gifted to future Pope Alexander VI by Pius II, contains superb examples of tapestries, goldwork and illuminated manuscripts. Back in Siena, the Pinacoteca Nazionale contains some of the greatest Sienese creations from Gothic to Mannerist.

Day 4

San Gimignano. San Gimignano is the most extraordinary of Italian hill towns. Scarcely changed for 600 years, it retains its medieval walls and fourteen 13th-century, hundred-foot tower houses. It also contains great frescoes, including Old and New Testament cycles in the Romanesque cathedral by the Sienese masters Bartolo di Fredi and Lippo Memmi, and the story of St Augustine by the Florentine painter Benozzo Gozzoli in a friary church.  

Day 5, Christmas Day

Free morning. There is, of course, the option of attending a church service, and of independently sauntering the streets and alleys and squares and imbuing the beauty of this incomparable little city. After Christmas lunch in the hotel restaurant, there is a walk encompassing a selection of Siena’s great piazze, fountains and buildings. 

Day 6

Arezzo. One of the main Etruscan city-states, Arezzo subsequently became a Roman city of strategic importance and then a free commune in the Middle Ages allied to the Ghibellines. The greatest artwork here – and one of the greatest cultural achievements in all Italy – is Piero della Francesca’s great fresco cycle The Legend of the True Cross, painted for the Franciscan order and executed over a 20-year period. See also the cathedral and the Romanesque church of Santa Maria. 

Day 7

Drive to Florence for the flight to London City, arriving c. 4.20pm.

Price – per person

Two sharing: £3,040 or £2,860 without flights. Single occupancy: £3,570 or £3,390 without flights.


Flights (Euro Traveller) with British Airways (Airbus 319); travel by private coach; hotel accommodation; breakfasts; 3 dinners and 2 lunches with wine, water, coffee; all admissions; all tips; all taxes; the services of the lecturer and tour manager.


Grand Hotel Continental, Siena: elegant and welcoming five-star, city-centre hotel housed in a former 17th-century palazzo. Rooms are varied in style. Single rooms are double for sole use.

How strenuous?

There is a lot of walking on this tour, some of it on uneven ground and much of it uphill. Coaches are not allowed inside the walls of any of the towns visited. Fitness is essential. Some days involve a lot of driving. Average distance by coach per day: 93 miles.

Are you fit enough to join the tour?

Group size

Between 10 and 22 participants.


Travel advice

Before booking, please refer to the FCDO website to ensure you are happy with the travel advice for the destination(s) you are visiting.