Tuscany contains seven World Heritage Sites and its capital, Florence, is one of the 100 most visited cities in the world. But beyond the historic architecture, art and sculpture of the region’s urban areas also lie breathtaking natural landscapes, from rugged coastlines to rolling hills, which remain glorious all year round.
(70km; 1 hour drive)
Renowned for both goldsmiths and antiques traders, Arezzo is an extraordinary city of art. Its ancient origins date back to around 9th century B.C. when it quickly became one of the most important cities in Tuscany.
Even though the medieval centre was destroyed during World War II, Arezzo’s many remaining historic monuments, churches and museums offer plenty of chances to step back in time. The Church of San Francesco is probably the most famous in Arezzo and features an incredible Early Renaissance fresco cycle, by Piero della Francesca. Also worth visiting are the Medicean Fortress, the Cathedral dedicated to San Donato, the Roman Amphitheatre and the Church of San Domenico, with its wooden crucifix by Cimabue.
For retail therapy Tuscan style, a lively flea market is held on the first Sunday of each month – packed with antique paintings, furniture, books, jewellery and more.
(110km; 1.5 hour drive)
Assisi is Umbria’s most famous town and one of its loveliest – thanks to a winning blend of medieval architecture, geranium-hung streets, lovely views and fountain-splashed piazzas.
As the famous birthplace of St. Francis, patron saint of Italy, Assisi is also an important pilgrimage site that hosts many religious conferences and festivals. The Basilica di San Francesco is one of the greatest monuments to 13th- and 14th-century Italian art, housing Giotto’s renowned fresco series of St. Francis’s life and other saintly relics.
Local ruins give a glimpse of Assisi’s Etruscan and Roman roots, while grand palaces and majestic castles tower above the tiled roofs. Quieter after sundown, the town is an ideal destination for cultural discoveries, tranquil evenings and hilltop charm.
(20km; 25 minutes’ drive)
Sitting on a hill above the Val d’Orcia, this ancient village’s central square is entirely taken up by an arcaded Roman piscina, or open pool, where the curative springs still bubble up at a steamy 52°C. Built by the Medici, Lorenzo the Magnificent and Saint Catherine of Siena are both reputed to have bathed here.
Sadly, modern visitors to Bagno Vignoni can no longer bathe in the piscina itself. But you can still enjoy the 30°C sulphur springs below the village, or the mineral-rich waters of one of the nearby spas.
From the 12th century, Bagno Vignoni became a stopover point for Christian pilgrims making their way to Rome – and therefore plays host to some fine Tuscan architecture. Rising above the piscina, in particular, is the small church of San Giovanni Battista: well worth a visit.
(50km; 1 hour drive)
Perhaps best known today as the setting for the book and film ‘Under the Tuscan Sun’, hillside Cortona can claim a long history and many architectural attractions, including some splendid churches. Make sure you visit the Duomo, the small Museo Diocesano across the piazza with its superb art collection, and the fascinating Museo dell’Accademia Etrusca with its collections of Etruscan and Roman items.
While you’re there, stop to enjoy the atmosphere of this medieval town, whose narrow, cobbled streets, jumble of small squares, lovely boutiques, excellent restaurants and colorful buildings are all delightful. The heart of Cortona is the Piazza della Repubblica, the main square, from where you can climb twisted streets to the town’s old fortress.
(28km; 30 minutes’ drive)
Having risen to prominence in the wars between Siena and Florence, this walled, medieval hill town is still dominated by an impressive fortress overlooking the surrounding plains.
World famous today for its Rosso and Brunello red wines, Montalcino’s narrow streets are also worth exploring for their picturesque sights and buildings. In particular the Abbey of Sant Antimo is one of the most beautiful in the region. On the last weekend of October, the town hosts a legendary archery festival which includes an all-day medieval feast inside the aforementioned fortress.
(20km; 25 minutes’ drive)
As well as being the highest of all the major Tuscan hill towns, Montepulciano is famed for its wines, especially the Vino Nobile di Montepulciano. For more than 1,200 years, this classic red has been aged and bottled in the warrens of stony cellars and tunnels carved into the town’s bedrock.
There’s much to see as well as taste here though. Montepulciano’s main street, the Corso, winds between crumbling Renaissance palaces and churches, with many perfect little squares and tiny alleyways to investigate along the way. The most intrepid explorers can climb the clock tower over the Palazzo Comunale for great vistas of the surrounding, wine-growing countryside. Keen shoppers, meanwhile, will enjoy a trip to the town’s bustling Thursday market.
(85km; 1 hour drive)
As the provincial capital of Umbria, Perugia’s historic centre rises above this beautiful region in a charming combination of cobbled alleys, arched stairways, piazzas and palazzi. With a prestigious university, the city has a lively student population, good shopping, fun bars and great restaurants.
Full of both Etruscan and Roman monuments, Perugia hinges around a single street, the Corso Vannucci, named after the city’s most celebrated artist, Perugino. Lined with bustling pavement cafés, this is one of Italy’s greatest people-watching opportunities, packed from dawn through to the early hours with a parade of tourists, students and trendsetters. Perugia hosts a chocolate festival every October and is the setting for one of Europe’s best jazz festivals – Umbria Jazz.
(10km; 10 minutes’ drive)
Not for nothing is the tiny, perfectly preserved village of Pienza widely known as the “ideal city of the Renaissance”. Created by the great humanist Enea Silvio Piccolomini, who later became Pope Pius II, Pienza was in fact the realization of a long-held vision.
Piccolomini had both the money and influence to transform his birthplace village, the humble Corsignano, into what he considered the utopian city should be. The result, Pienza, was designed to exemplify the principles and philosophy of classical times and the great Italian Renaissance. Its cost was astronomical, but the cathedral, papal and bishop’s palaces, and the core of a town, were completed in just three years.
Food-wise, Pienza is noted for its pecorino, an aged sheep’s milk cheese. Flavored by a unique set of local herbs, this local delicacy even boasts its own festival, held on the first Sunday in September. A flower festival also takes place here over the second weekend in May.
(12km; 15 minutes’ drive)
Back in the Middle Ages, San Quirico enjoyed a strategic position on the Via Francigena, the road which linked Rome with Canterbury, and flourished as a result. To this day you can see the architectural proof of the ancient town’s prosperity – in the towering form of its 15th-century walls, still topped with 14 turrets.
In San Quirico’s medieval centre you’ll find the Romanesque church of Collegiata dei Santi Quirico e Giuditta, the Palazzo Chigi and the Church of San Francesco, as well as the Ospedale della Scala – a monument to pilgrims. If you’re around for the third Sunday in June, why not catch the town’s Festa del Barbarossa? This lively festival commemorates Frederick I Barbarossa’s historic visit to San Quirico in 1154, and features flag and archery competitions a historical parade and a re-enactment of the meeting between Barbarossa and the envoy of Pope Adrian IV.
(60km; 1 hours’ drive)
Siena is a captivating and somewhat flamboyant town of medieval buildings, dominated by Tuscany’s tallest tower and dazzling Duomo (cathedral). At its physical and spiritual heart is arguably Italy’s loveliest square: the sloping, scallop-shaped Piazza Il Campo – also the setting for the thrilling Palio bareback horse race held every summer.
Siena’s Duomo and Palazzo Pubblico are two of the purest expressions of Italian Gothic architecture, and the best of the city’s paintings – collected in the Museo Civico and Pinacoteca Nazionale – are in the same tradition. But perhaps the finest example of Sienese Gothic is Duccio’s Maestà, on show in the outstanding Museo dell’Opera. Art lovers will also find a selection of impressive frescoes on the walls of another of Siena’s museums, Santa Maria della Scala.