Tuscany and Umbria in One Week

Florence contains more Renaissance art per square meter than any city in the world. This is not hyperbole; it's a logistical challenge. The Uffizi Gallery, home to Botticelli's Birth of Venus, Leonardo's Adoration of the Magi, Raphael, Michelangelo, and Titian, requires at minimum three hours and preferably more. Book timed-entry tickets well in advance at uffizi.it; the queues without reservations are long and unforgiving.

Michelangelo's Davidat the Galleria dell'Accademia is a separate ticket and separate reservation: €16 (about $18) at the door, also requiring advance booking. It takes less time than the Uffizi but is its own unmissable experience. The statue is 17 feet tall; photographs do not prepare you for the actual scale.

The Duomo complex (Brunelleschi's dome, the Baptistery's bronze doors, the campanile) is free to look at from outside and worth doing so at length. The dome climb (463 steps, no elevator, a narrow spiral passage) has a fee and requires advance time-slot booking at the Opera del Duomo website. The view from the top over the terracotta rooftops of Florence is one of the set-piece moments of any Italian trip.

Eat in the Oltrarno neighborhood across the river. The streets between thePonte Vecchioand thePitti Palaceare slightly less tourist-saturated than the historic center north of the river. Dinner reservations at a serious Florentine restaurant (Bistecca alla Fiorentina, Ribollita, Pappardelle al Cinghiale) require at least two to three days advance booking in peak season.

A practical note on ZTL zones: Florence's historic center has a Zona Traffico Limitato, a restricted traffic zone that is aggressively enforced by cameras. Do not drive into the historic center in a rental car. Book a hotel outside the ZTL or use the designated “hotel drop-off approach” your hotel specifies. The fine for an unauthorized entry starts at €80 (about $90) per camera and can reach €335 (about $380), and there are many cameras. Pick up your rental car at a location outside the ZTL zone.

Siena is an hour south of Florence and deserves more attention than it typically gets. The Piazza del Campo, the shell-shaped medieval piazza that hosts the famous Palio horse race every July and August, is one of the finest public squares in Italy. The Siena Duomo is more ornate and less visited than Florence's, with an extraordinary inlaid marble floor that is uncovered only in August and September. Book the cathedral complex online.

TheChiantiwine region runs south of Florence and north of Siena, strung along the SR222 road through villages with names that appear on wine labels: Greve, Panzano, Radda, Gaiole. Most wineries along this road offer tastings and many do lunch. This is the right approach to the countryside: drive slowly, stop when a sign for a cantina appears at the end of a cypress-lined gravel road, and accept that the afternoon's schedule will dissolve pleasantly.

The Val d'Orcia, the UNESCO-listed landscape valley south of Siena, is the postcard image of Tuscany: rolling hills with cypress trees silhouetted against the morning light, medieval towers above medieval towns, vineyards producing Brunello di Montalcino and Vino Nobile di Montepulciano.Pienza, a Renaissance planned town of improbable perfection, sits at the center of the valley and warrants an afternoon.

San Gimignano, the Manhattan of medieval Tuscany with 14 surviving medieval towers rising above the hilltop, is genuinely worth the stop. It is also genuinely crowded from June through September. Go early or in the shoulder season and the town recovers its quality. The Museo Civico houses the Sala di Dante and Pinacoteca rooms with works by Benozzo Gozzoli, Filippino Lippi, and Pinturicchio. The gelateria on the main square has won the World Gelato Championship multiple times. Both things are worth your time.

Volterrasits 30 kilometers southwest and is much less visited: an Etruscan city with Roman amphitheater ruins, the best alabaster workshops in Tuscany, and a lived-in feel. An afternoon here resets the tourist register.

Umbria begins roughly where Tuscany ends, just south of Siena. The two regions are separated by no visible boundary and share the same landscape of hilltop towns above rolling green countryside. The distinction is in the crowds. Umbria hasn't been discovered to the same degree, which means quieter streets, shorter queues, and slightly lower prices.

Assisiis the mandatory Umbrian stop. The birthplace of St. Francis, Assisi is a walled hilltop town of pink-stone streets rising above the Spoleto valley, housing the Basilica di San Francesco, a 13th-century basilica of two superimposed churches, upper and lower. Here you’ll find Giotto's fresco cycle of St. Francis's life in the upper church. This work is widely regarded as one of the turning points in Western art history. Entry is free. We suggest arriving early before the tour groups so you can spend 45 minutes, the necessary time, to truly absorb the work.

Perugiais Umbria's largest city and the logical final base. A proper university town with an active restaurant and bar scene, good hotels in the historic center, and a National Gallery of Umbria containing works by Perugino and Pinturicchio. ThePerugia airportconnects to Rome and other Italian cities, making it a sensible departure point; alternatively, the train back to Florence or Rome takes two hours.

Orvietois a 45-minute detour south of Perugia and worth it: Built on a volcanic plug rising from the valley floor, Orvieto is home to a cathedral facade covered in Gothic mosaics that is, in the judgment of many visitors, more beautiful than any other cathedral front in Italy. The St. Patrick's Well, a double-helix staircase that let donkeys descend and ascend simultaneously to carry water, is the 16th-century engineering feat that it sounds like.

Book a compact car, navigate by GPS, but allow for extra time assuming the estimates for driving routes will be 20 to 30% longer than maps suggest because the roads don't move very quickly. And you don’t drive like an Italian.

The shoulder season, late April through May and September through October, is the consistently better choice to visit Tuscany. In July and August you’ll find peak crowds and peak pricing. The landscape looks the same in October, but the lines are shorter and the temperatures more reasonable.