Tuscany's Rolling Hills: Cypress Trees, Chianti, and Medieval Towns

Tuscany is the region of Italy that most closely matches the image of the country that the rest of the world carries in its imagination — the rolling hills of the Val d'Orcia, the cypress trees that line the roads between the hilltowns, the vineyards of Chianti and Brunello, and the medieval cities of Siena, San Gimignano, and Volterra that rise from the landscape like illustrations from a history book.

Florence, the capital of Tuscany, is the finest art city in the world — a compact historic centre of extraordinary density, where the Uffizi Gallery, the Accademia (home of Michelangelo's David), the Bargello, and the Palazzo Pitti contain more masterpieces of Renaissance art than any other city on Earth. The Duomo — Brunelleschi's dome, the largest masonry dome ever built — dominates the skyline and the climb to the top offers the finest view of Florence.

Siena is the finest medieval city in Italy — a city of Gothic architecture, narrow streets, and the Piazza del Campo, one of the most beautiful public spaces in Europe. The Palio di Siena, a bareback horse race around the Campo that takes place twice a year (July 2 and August 16), is the most intense civic event in Italy — a race that lasts 90 seconds but is preceded by months of political manoeuvring between the city's 17 contrade (districts).

The Val d'Orcia, south of Siena, is the most photographed landscape in Tuscany — a UNESCO World Heritage Site of rolling hills, isolated farmhouses, and the cypress-lined roads that appear on every Tuscany travel poster. The best time to photograph it is in spring (April to May), when the wheat is green and the poppies are in bloom, or in autumn (September to October), when the harvest is underway and the light has a golden quality.

The Chianti wine region, between Florence and Siena, is the heart of Tuscan wine culture — a landscape of vineyards, olive groves, and medieval castles where the Sangiovese grape produces the Chianti Classico that is one of Italy's finest wines. The Strada del Vino e dell'Olio del Chianti Classico is a driving route through the region that passes the finest estates — Antinori, Badia a Coltibuono, Castello di Brolio — and offers tastings at each.

San Gimignano, the 'medieval Manhattan' of Tuscany, is a hilltop town famous for its 14 surviving medieval towers — the remnants of the 72 that once competed for dominance of the skyline. The town is genuinely beautiful but genuinely crowded in summer, and the best strategy is to arrive early in the morning or stay overnight, when the day-trippers have gone and the town recovers its medieval character.

The best time to visit Tuscany is in spring (April to June) or autumn (September to October), when the weather is mild, the landscapes are at their most beautiful, and the wine harvest (vendemmia) in September and October fills the region with activity. The summer months (July and August) are hot and crowded, particularly in Florence and the hilltowns. The winter months are cold but quiet, and the museums and galleries are at their most accessible.