Arezzo, Tuscany.

South-eastern Tuscany's quiet corner — medieval hilltop towns, the Piero della Francesca trail and open country between Siena and the Apennines.

On Arezzo

Arezzo,
from Smaranda.

Arezzo is the working city of eastern Tuscany, rich long before tourism and largely indifferent to it, which is precisely its appeal. Piero della Francesca's Legend of the True Cross fresco cycle in the basilica of San Francesco is one of the summits of Italian painting, seen by a fraction of the crowds that queue for lesser rooms in Florence; the sloping Piazza Grande hosts a jousting tournament twice a year and Italy's oldest antiques fair every month; and Roberto Benigni filmed the first half of Life Is Beautiful in these streets.

None of our houses stands in Arezzo itself, and none needs to: the city works as the cultural long day of an eastern itinerary, about an hour from the Val d'Orcia estates and similar from the Chianti houses, and the train from Florence does it in under an hour for guests based on the Florence side.

The Fair and the Frescoes

The Fiera Antiquaria fills the Piazza Grande and the surrounding streets on the first weekend of every month, several hundred dealers ranging from museum-grade furniture to honest junk, and it is the best antiques hunting in central Italy. Pair it with a booked slot for the Piero frescoes, restored to almost uncomfortable freshness, and lunch in one of the city's unhurried osterie, and Arezzo delivers a day no purpose-built tourist town can match. Piero completists continue east: Sansepolcro, his birthplace, keeps the Resurrection, and Monterchi the Madonna del Parto.

When to come

Any month with a first weekend, for the fair. June and September bring the Giostra del Saracino; high summer in the city is hot but workable, the frescoes do not mind the weather.

Towns worth knowing

Arezzo: The Piero cycle, the Pieve's arcaded apse, Vasari's own frescoed house.
Anghiari: Hill town of the famous battle; hand-weaving workshops still operating.
Sansepolcro: Piero della Francesca's birthplace; the Resurrection is worth the extra half hour.
Poppi: The Casentino's castle town, guarding the upper Arno forests.

Best for

Art pilgrims after Piero della Francesca
Antiques hunters, on first weekends
A city day without Florence's crowds
Rainy-day plans from any eastern villa

Practicalities

The train is the honest advice from the Florence side, under an hour from Santa Maria Novella. Driving, park below the walls at Pietri or Eden and ride the escalators up; allow an hour from the Val d'Orcia.