Tuscany, Italy

Florence is Tuscany's artistic crown — the city where the Renaissance happened and where its legacy is concentrated in a density that staggers even the most experienced traveler. The Uffizi Galleries are the most visited museum in Italy, drawing over 4 million visitors annually, and house Botticelli's Birth of Venus and Primavera, Leonardo da Vinci's Annunciation, Michelangelo's Holy Family, Caravaggio, Raphael, Titian, and Giotto in one continuous sequence of masterpieces. Book timed entry tickets online weeks ahead to avoid being turned away. The Florence Cathedral — Cattedrale di Santa Maria del Fiore — is crowned by Brunelleschi's dome, engineered in the early 15th century without precedent or supporting scaffolding and still the largest masonry dome ever built. Climbing the dome's interior requires a separate timed ticket and delivers a view over the city's terracotta roofscape from inside the fresco.

Siena is Florence's great rival and arguably its more complete medieval experience. The Piazza del Campo — a shell-shaped medieval square sloping down to the Gothic Palazzo Pubblico and its soaring Torre del Mangia — is one of the finest public spaces in Italy, genuinely beautiful in a way that no photograph conveys adequately. The Siena Cathedral (Duomo di Siena) with its zebra-striped marble and its floor inlaid with 56 elaborate marble panels is remarkable in ways that rival Florentine churches. The Palio di Siena — the bareback horse race around the Piazza del Campo held on July 2 and August 16 each year — is one of the most intensely local and emotionally charged sporting events in Europe, rooted in centuries of neighborhood rivalries. For the Palio, accommodation books out 12 months ahead.

The Val d'Orcia is the landscape that has defined the world's visual idea of Tuscany — gentle rolling hills covered in wheat, sunflowers, and vineyards; cypress trees marking farmhouse lanes and chapel approaches; hilltop medieval towns presiding over river valleys. Declared a UNESCO World Heritage Site in 2004, the valley stretches south of Siena between the towns of Pienza, Montalcino, Montepulciano, and San Quirico d'Orcia. The road between San Quirico and Montalcino on a clear October morning, with the vineyards turning gold and the towers of Montalcino visible at the hilltop, is among the most beautiful drives in Italy. Pienza — a Renaissance ideal city laid out by Pope Pius II in the 1460s — and Montepulciano — a hilltop town of Renaissance palazzos sitting above the Vino Nobile vineyards — are each worth a full day.

The Chianti wine region stretches through the hills between Florence and Siena — vineyards producing Sangiovese-based Chianti Classico, the most celebrated red wine appellation in Tuscany. The Chiantishire nickname given by British expatriates reflects the extraordinary number of foreigners who have made their homes here over the decades, drawn by the combination of landscape, wine, food, and proximity to Florence (30 to 40 minutes by road) and Siena (35 minutes). A wine tour through Greve, Castellina, Radda, and Gaiole — stopping at family estates like Badia a Coltibuono, Castello di Ama, and smaller organic producers — is the quintessential Chianti experience and superior to the commercial tasting rooms on the main roads.

San Gimignano, the medieval hilltop town whose 14 surviving towers from the original 72 create a skyline unchanged since the 13th century, is one of the most photographed towns in Italy and correspondingly crowded in summer. Visit early in the morning before the day-trip coaches arrive — by 8am the streets belong to the residents and the light on the towers is at its most beautiful. Lucca, the walled city whose Renaissance fortifications are so broad that residents cycle along the top of them, is one of Tuscany's most genuinely livable cities — still relatively undiscovered by mass tourism despite its extraordinary medieval and Renaissance center.