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Galleria degli Uffizi, Florence

Florence has many museums, but the Uffizi is king. Walking its halls is like stepping into an art history textbook, except here you’re looking at the genuine article—masterpieces by Leonardo, Michelangelo, Raphael, Botticelli, Caravaggio, and dozens of other luminaries. When planning your visit, make a point to reserve a ticket in advance.

Duomo, Florence

The Cathedral of Santa Maria del Fiore, commonly known as the Duomo, is Florence’s most distinctive landmark, sitting at the very heart of the city and towering over the neighboring rooftops. Its massive dome is one of the world’s great engineering masterpieces. For an up-close look, you can climb the 463 steps to the top—then gaze out at the city beneath you.

Leaning Tower, Pisa

This tower may be too famous for its own good (it’s one of Italy’s most popular tourist attractions), but there’s something undeniably appealing about its perilous tilt, and climbing to the top is a kick. The square on which it sits, known as the Campo dei Miracoli, has a majestic beauty that no quantity of tourists can diminish.

Piazza del Campo, Siena

The sloping, fan-shaped square in the heart of Siena is one of the best places in Italy to engage in the distinctly Italian activity of hanging out and people-watching. The flanking Palazzo Pubblico and Torre del Mangia are first-rate sights.

San Gimignano, Central Tuscany

This classic Tuscan hill town has been dubbed a “medieval Manhattan” because of its numerous towers, built by noble families of the time, each striving to outdo its neighbors. The streets fill with tour groups during the day, but if you stick around until sunset the crowds diminish and you see the town at its most beautiful.

Abbazia di Sant’Antimo, Southern Tuscany

In a peaceful valley, surrounded by gently rolling hills, olive trees, and thick oak woods, Sant’Antimo is one of Italy’s most beautifully situated abbeys—and a great “off the beaten path” destination. Stick around for mass and you’ll hear the halls resound with Gregorian chant.

Palazzo Ducale, Urbino, the Marches

East of Umbria in the Marches region, Urbino is a college town in the Italian style—meaning its small but prestigious university dates to the 15th century. The highlight here is the Palazzo Ducale, a palace that exemplifies the Renaissance ideals of grace and harmony.

Basilica di San Francesco, Assisi

The basilica, built to honor Saint Francis, consists of two great churches: one Romanesque, fittingly solemn with its low ceilings and guttering candles; the other Gothic, with soaring arches and stained-glass windows (the first in Italy). They’re both filled with some of Europe’s finest frescoes.

Duomo, Orvieto

The facade of Orvieto’s monumental Duomo contains a bas-relief masterpiece depicting the stories of the Creation and the Last Judgment (with the horrors of hell shown in striking detail). Inside, there’s more glorious gore in the right transept, frescoed with Lucca Signorelli’s Stories of the Antichrist and the Last Judgment.

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