Squeezed between Siena and Florence, this landscape of wooded hills, isolated farms and pretty villages is prime wine country. Known as Chiantishire since it’s become home or second-home to so many British ex-patriots, it is prime touring territory – just follow the SR 222, the Chiantigiana, and stop off at the vineyards and many enoteche (wine shops) that line your route.  

The Duomo complex

Brunelleschi’s famous dome is a triumph of Renaissance engineering, while Ghiberti’s golden doors on the Baptistery are considered by some to be the real heralds of the beginning of the Renaissance. Climb the Campanile (Bell Tower) for a – literally – breathtaking view of the city, then admire original sacred artworks in the museum.

Uffizi Gallery

Italy’s top treasure house of paintings takes you from medieval times to the 18th century. Masterpiece follows masterpiece, with works by Giotto, Filippo Lippi, Piero della Francesca, Raphael, Caravaggio and Dürer. Perhaps the most famous works are Leonardo da Vinci’s Annunciation, Botticelli’s Birth of Venus and Michelangelo’s Holy Family.

San Marco

The sense of place envelops you when you enter this Dominican monastery – you almost feel as if the monks have only just left their cells. The rabidly religious Savonarola lived here, as did devout and gentle Fra Angelico – whose frescoes still adorn the walls.

Michelangelo’s David

Of all the works of art associated with Florence, it is this, Michelangelo’s mighty David, which once stood outside the Palazzo Pubblico. For the sculptor it symbolized the republican city. Carved out of a block of marble that nobody else wanted, it now stands on a plinth in the Galleria dell’Accademia – pure, perfect and alone. 

Il Campo & the Palazzo Pubblico

The Campo, the shell-shaped piazza at the heart of Siena, is one of the great sights of Italy. It’s surrounded by sombre medieval buildings, which include the almost triumphal Palazzo Pubblico, or town hall. Frescoes on its walls include Ambrogio Lorenzetti’s vivid reminder of the importance of wielding power wisely – his Allegories of Good and Bad Government. 

Duomo, Siena

Siena’s 12th-century Duomo (cathedral) is so lavish you hardly know where to look first: striped columns, a marble floor, Nicola Pisano’s pulpit and the vivid frescoes of the Piccolomini Library. Behind the Duomo is the ‘crypt’, where pilgrims once washed before entering the cathedral.

San Gimignano

It’s one of the most photographed places in Tuscany and no wonder, for San Gimignano’s medieval towers make an arresting sight. They were built first for defence and later to show off the wealth of its inhabitants. The town attracts vast numbers of tourists, who come to see the towers, admire the frescoes in the Collegiata – and try the award-winning ice cream.

San Francesco Church, Arezzo

Come here to see Piero della Francesca’s celebrated fresco cycle depicting the Legend of the True Cross. Piero, famously interested in geometry and mathematics, did not just paint biblical scenes but gave them a contemporary twist.


This town is just irresistibly pretty, with geraniums blooming from terracotta tubs, medieval alleyways and streets so steep your calves will ache. There are wine shops and restaurants, a great gelateria, Etruscan tombs – and a shimmering Annunciation by Fra Angelico.

Campo dei Miracoli

A grassy square filled with dazzling white buildings – you can easily see how it earned the name ‘Field of Miracles’. Here is the most celebrated architectural muck-up in the world, the Leaning Tower of Pisa. And here too is Pisa’s glorious Cathedral and its exquisite Baptistery.


This lovely walled town lies to the north of Pisa. Inside its walls you’ll feel as if you’ve entered a different age. There are medieval towers, palaces, artworks such as the 13th-century Volto Santo – a revered wooden crucifix – lovely individual shops and a piazza that preserves the shape of its earlier incarnation as a Roman amphitheatre.

The Garfagnana

Life in the Garfagnana seems even slower than in the rest of Tuscany. This rugged area of thickly wooded slopes has a rich history all its own, with quiet hamlets, isolated churches and some rewarding walking trails.


Wine buffs flock here to taste its famous Vino Nobile, but there’s definitely more to Montepulciano than some good glasses of red. It’s a well-preserved hill town, perched dramatically on a ridge, with fine churches, lively festivals and good bars and restaurants.


Small but perfectly formed, Pienza is the village that was remodelled into a harmonious Renaissance city by Pope Pius II, its most famous son. The embodiment of one man’s vision, it symbolizes the ideals and imagination that characterized 15th-century Tuscany. It’s also a lovely spot for lunch, with great views over the surrounding countryside.

Monte Oliveto Maggiore

An avenue of cypress trees leads to this isolated Benedictine abbey south of Siena. Come here to see the frescoes on the walls of its Great Cloister: some are by Luca Signorelli; others – the most lively – by Il Sodoma, who cheekily painted himself in one of the holy scenes.


Wild, rather windswept and isolated – that’s Volterra. It has a unique atmosphere, perhaps because of its location, perhaps because of its Etruscan past. Come and see the gilded ceiling of the Duomo, buy a sculpture made of snowy white alabaster, and ponder on the enigmatic figures that adorn the Etruscan burial urns.

Parco Naturale della Maremma

The Uccellina Natural Park, as it’s often called, is a glorious protected natural area along the coast of the Maremma. There are pristine beaches, umbrella pine trees and a rich variety of flora and fauna. It’s the hidden face of Tuscany, and quite beautiful with it.


Deep in the southeast corner of the Maremma, close to the border with Lazio, Pitigliano is one of the most individual of Tuscan towns. With a rich legacy of Etruscan and later Jewish settlement, it has a character that is all its own – rising from the tufa like some magical beast.

Massa Marittima

So far only the Germans seem to have discovered this little town, which says much for their taste as it’s a real gem. The harmonious central piazza is as picturesque as they come, all focused on its lovely Romanesque Cathedral.

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