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Off Piazza del Municipio, Sant’Agostino has a trove of paintings, starring the 13th-century St Francis by Margheritone d’Arezzo, Gaddi’s Madonna and Child and Bartolomeo della Gatta’s St Francis Receiving the Stigmata .

Charming little brick town. Benozzo Gozzoli teamed with Giusto di Andrea on the Giustiziati tabernacle in Santi Michele e Jacopo church. Also inside, a 1503 bust and 1954 tombstone commemorate Decameron author Boccaccio (1313–75), who may have been born here; the Casa del Boccaccio, in which he passed his final years, is now a small museum and study library.

This charterhouse, home to Carthusian monks from the 1300s to 1956, now serves the Cistercian Order. The building retains an original small monk’s church, a visitable cell and peaceful Renaissance cloisters set with della Robbia terracotta tondi and a small gallery of the Pontormo frescoes (1523–5).

It is fortunate that the spa waters of Acqua Santa clean the liver, for Chianciano lies at the end of a wine road from Montalcino past the Chianti and Montepulciano. This group of thermal spas – with waters and mud packs to invigorate the body – is linked to the hill town of Chianciano Alto by a long string of hotels.

Tuscany’s famous wine region has vineyards and castles, market towns and monasteries.

The fine Museo Archeologico Nationale Etrusco in Chiusi contains bucchero (black Etruscan earthenware), bronzes, anthropomorphic canopic jars and even a few 2nd-century BC painted funerary urns. Apply here to visit the best decorated tombs in the valley.

The 12th-century Duomo is swathed in trompe-l’oeil frescoes (1887–94) that look like medieval mosaics. Next door, the Museo della Cattedrale preserves 15th-century illuminated scores from Monte Oliveto Maggiore. Meet here for guided visits to the Etruscan-carved “Labirinto di Porsenna” tunnels.

From the Duomo’s dome in Florence to countless belltowers, Tuscany offers dozens of fun scrambles up to dramatic lookout points, many reached via tight, evocatively medieval stairs.

Enter from the west to pass under Baccio d’Agnolo’s Mannerist Palazzo Campana gate (1539). The Duomo features a Giambologna/Pietro Tacca bronze crucifix and, in Mino da Fiesole’s tabernacle, a nail said to be from Christ’s cross. Palazzo Pretorio’s archaeological museum is most interesting for the 1920s political graffiti scrawled on this former prison’s inner walls by imprisoned Communists. The (intentionally) sgraffito-covered façade of Palazzo dei Priori hides a small museum of Sienese paintings.

Cortona is the quintessential Tuscan hill town with its Etruscan tombs, medieval alleys, Renaissance art and excellent restaurants.

This Etruscan settlement above the Chiana Valley is a trove of ancient tombs and Renaissance art. Stony buildings, steep streets and interlocked piazze characterize the centre. The upper half of Cortona has a sanctuary, the 16th-century Medici fortress, numerous gardens and little-known lookouts.