This road-trip route zips in a figure of eight around Franciscan monasteries, Etruscan castles and medieval hamlets across Tuscany. Zoom down narrow streets watched over by coy Renaissance torsos, stopping off at cafés and wine bars to meet the locals—old ladies waving handkerchiefs, men sipping espressos at Formica tables. Outside Florence, hunt for truffles at Tenuta Torciano Winery, find restaurants hidden down driveways lined with cypress trees and explore walled cities behind sprawling vineyards and sun-kissed olive groves. —Toby Skinner
Where to stay: Villa San Michele, once a Franciscan monastery, in the Fiesole hills overlooking Florence.
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Bari to Salento
Approximate time: one-and-a-half hours
Puglia’s dry Salento region is the Italian answer to Cornwall—with its olive groves, cliff-jumping kids and unfussy cucina povera. Coastal roads run almost all the way around the heel, from the plunging limestone stacks and rocky bays of the outer east coast to the limpid tranquillity of the west coast, with white-sand beaches including the long and gloriously named Punta Prosciutto. At its core, Greek-influenced Salento is an escape—the opposite of a guided tour, it is a place of wild swims under limestone bluffs and open roads through the ochre landscape. —Toby Skinner
Where to stay: Stay in the handsome town of Gagliano del Capo, where the converted 19th-century Palazzo Daniele is the smartest boutique hotel around.
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Naples to Salerno
Approximate time: four-and-a-half hours