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Etruscan Pitigliano seems to grow right out of its rocky terrain. This hill town’s greatest sight is its medieval self, though the Palazzo Orsini castle (a 13th-century structure, enlarged by Giuliano da Sangallo) houses a few modest museums of local Etruscan finds (“Museo Civico Archeologico”) and its own rooms (“Palazzo Orsini”). The synagogue offers tours (Wednesday, Friday and Sunday) of Pitigliano’s significant Jewish heritage, which all but vanished with Nazi deportations.

This brawny Mannerist mansion served as Florence’s royal home from 1560 until the 1860s, when Florence did a stint as Italy’s capital. Backed by the elaborate Boboli Gardens, the palace’s seven museums include the excellent Galleria Palatina of late Renaissance/early Baroque painting.

The Grand Ducal home has many works from the Medici’s collections.

One of the least pretentious major Montalcino vineyards, producing an award-winning velvety Brunello.

Federico Carletti has made Poliziano one of the top producers in Montepulciano, the first to introduce the cru concept (grapes from a single vineyard) to Vino Nobile with Vigneto Caggiole. The vineyards are private, but there is a sales outlet with free tastings.

The shops hanging from both sides of Taddeo Gaddi’s 1354 “old bridge” have housed gold- and silversmiths since Ferdinando I evicted the butchers in the 16th century (his private corridor from the Uffizi to the Pitti passed overhead, and he couldn’t stand the smell). Even the Nazis, blowing up bridges to slow the Allied advance, found the span too beautiful to destroy and instead took down the buildings at either end.

Mixing Andrea del Sarto’s experimentation with twisting figures and Michelangelo’s use of non-primary colours, Pontormo took these concepts to vivid and complex extremes.

Stranded up a northern spit of Tuscany is Pontrémoli and its Museo delle Statue-Stele. Some of the museum’s 20-odd prehistoric menhirs (tombstone-like slabs) date from 3000 BC, the more elaborate ones from 200 BC.

Cardinal Giulio fared well when running Florence himself, but once he became Pope spent his energies fighting Emperor Charles V, leaving Florence in the hands of his incompetent young relatives Alessandro and Ippolito.

Lorenzo the Magnificent’s son continued to call the shots from Rome, exclaiming “God has risen us to the papacy; let us enjoy it.” The younger brother and nephews he groomed to take over Florence all died, and so his cousin, Cardinal Giulio, took the reins.