A Great Central Italy Itinerary

Day 1: Florence

If you're coming in on an international flight, you'll probably settle in Florence in time for an afternoon stroll or siesta (depending on your jet-lag strategy) before dinner.

Logistics: On your flight in, read through the restaurant listings in this guide and begin anticipating the first dinner of your trip. Look for a place near your hotel, and when you arrive, reserve a table (or have your concierge do it for you).

Making a meal the focus of your first day is a great way to ease into Italian life. Note that Sunday and Monday are favorite closing days for many Florence restaurants, and Monday sees most important museums closed.

Day 2: Florence

Begin your morning at the Uffizi Gallery (reserve your ticket in advance). The extensive collection will occupy much of your morning. Next, take in the neighboring Piazza della Signoria, one of Florence's impressive squares, then head a few blocks north to the Duomo. There, check out Ghiberti's famous bronze doors on the Battistero (they're high-quality copies; the originals are in the Museo dell’Opera del Duomo), and work up an appetite by climbing the 463 steps to the cupola of Brunelleschi's splendid cathedral dome, atop which you'll experience a memorable view.

Spend the afternoon relaxing, shopping, and wandering Florence's medieval streets; or, if you're up for more of a journey, head out to Fiesole to experience the ancient amphitheater and beautiful views of the Tuscan countryside.

Day 3: Florence

Keep the energy level up for your second full day in Florence, sticking with art and architecture for the morning, trying to see most of the following: Michelangelo's David at the Galleria dell'Accademia, the Medici Chapels, the Palazzo Pitti and Boboli Gardens, and the churches of Santa Maria Novella and Santa Croce.

If it's a clear day, spend the afternoon on a trip to Piazzale Michelangelo, high on a hill, for sweeping views of idyllic Florentine countryside. Given all the walking you've been doing, this would be a good night to recharge by trying the famed bistecca alla fiorentina (a grilled T-bone steak with olive oil).

Logistics: You can get up to the Piazzale Michelangelo by taxi or by taking Bus No. 12 or 13 from the Lungarno. Otherwise, do your best to get around on foot; Florence is a brilliant city for walking.

Day 4: San Gimignano

Now that you've been appropriately introduced to the bewildering splendor of Renaissance Italy, it's time for a change of pace—and time for a rental car, which will enable you to see the back roads of Tuscany and Umbria. After breakfast, head on out. On a beautiful day the lazy drive from Florence to San Gimignano, past vineyards and typical Tuscan landscapes, is truly spectacular.

The first thing that will hit you when you arrive at the hill town of San Gimignano will be its multiple towers. The medieval skyscrapers of Italy once occupied the role now played by Ferraris or Hummers: they were public displays of wealth and family power. After finding your way to a hotel in the old town, set out on foot and check out the city's turrets and alleyways, doing your best to get away from the trinket shops. Later, enjoy a leisurely dinner with the light but delicious local white wine, Vernaccia di San Gimignano.

Logistics: Some hotels might be able to coordinate with some rental-car agencies so that your car can be brought to your hotel for you. The historic center of Florence is closed to nonresidents’ cars (including rentals). You can drive out of the center, but must give your license plate number to your hotel if you drive in—there’s a heavy fine otherwise.

Once you navigate your way out of Florence (no easy task), San Gimignano is only 57 km (35 miles) to the southwest, so it's an easy drive; you could even take a detour on the SR222 (Strada Chiantigiana), stop at one of the Chianti wine towns, and visit a winery along the way.

Day 5: Siena

In the morning, set out for nearby Siena, which is known worldwide for its Palio, a festival that culminates in an elaborate horse-race competition among the 17 contrade (medieval neighborhoods) of the city. Because of the enormous influx of tourists, especially in summer, Siena isn't everyone's cup of tea, but it's still one of Tuscany's most impressive sights.

However many tourists you have to bump elbows with, it's hard not to be blown away by the city's precious medieval streets and memorable fan-shape Piazza del Campo.

Not to be missed while in town are the spectacular Duomo, the Battistero, and the Spedale di Santa Maria della Scala, an old hospital and hostel that now contains an underground archaeological museum.

Logistics: It's a short and pleasant drive from San Gimignano to Siena, but once there, parking can be a challenge. Look for the stadio (soccer stadium), where there's a parking lot that often has space. Try to avoid arriving in Siena on Wednesday morning—the town’s weekly market is in full swing, and the traffic and parking can be nightmarish.

Day 6: Arezzo/Cortona

Get an early start, because there's a lot to see today. From Siena you'll first head to Arezzo, home to the Basilica di San Francesco, which contains important frescoes by Piero della Francesca. Check out the Piazza Grande along with its beautiful Romanesque church, Pieve di Santa Maria.

Try to do all of this before lunch, after which you'll head straight to Cortona. If Arezzo didn't capture your imagination, Cortona, whose origins date to the 5th century BC, will. Olive trees and vineyards give way to a medieval hill town with views over ridiculously idyllic Tuscan countryside and Lake Trasimeno. Cortona is a town for walking and relaxing, not sightseeing, so enjoy yourself, wandering through the Piazza della Repubblica and Piazza Signorelli,and perhaps doing a bit of shopping.

Logistics: Siena to Arezzo is 63 km (39 miles) on the E78. From Arezzo to Cortona, it's 30 km (18 miles)—take S71.

Day 7: Assisi

Today you'll cross over into Umbria, a region just as beautiful as Tuscany but still less trodden. Yet another impossibly beautiful hill town, Assisi, is the home of St. Francis and host to the many religious pilgrims that come to venerate his legacy. A visit here is the most treasured memory of many a traveler's visit to Italy.

Upon arriving and checking into your lodging, head straight for the Basilica di San Francesco, which displays the tomb of St. Francis and unbelievable frescoes. From here take Via San Francesco to Piazza del Commune and see the Tempio di Minerva before a break for lunch. After lunch, see San Rufino, the town cathedral, and then go back through the piazza to Corso Mazzini and see Santa Chiara. If you're a true Franciscan, you could instead devote the afternoon to heading out 16 km (10 miles) to Cannara, where St. Francis delivered his sermon to the birds.

Logistics: From Cortona, take the S71 to the A1 autostrada toward Perugia. After about 40 km (24 miles), take the Assisi exit (E45), and it's another 14 km (8 miles).

Day 8: Spoleto

This morning will take you from a small Umbrian hill town to a slightly bigger one: Spoleto, a walled city that's home to a world-renowned arts festival each summer. But Spoleto's own renown rivals that of its festival. Its Duomo is wonderful. Its fortress, La Rocca, is impressive. And the Ponte delle Torri, a 14th-century bridge that separates Spoleto from Monteluco, is a marvelous sight, traversing a gorge 260 feet below and built on the foundations of a Roman aqueduct.

See all these during the day, stopping for a light lunch of a panino (sandwich) or salad, saving your appetite for a serious last dinner in Italy: Umbrian cuisine is excellent everywhere, but Spoleto is a memorable culinary destination. Do your best to sample black truffles, a proud product of the region; they're delicious on pasta or meat.

Logistics: One school of thought would be to time your visit to Spoleto's world-renowned arts festival that runs from mid-June through mid-July. Another would be to do anything you can to avoid it. It all depends on your taste for big festivals and big crowds.

The trip from Assisi to Spoleto is a lovely 47-km (29-mile) drive (S75 to the S3) that should take you less than an hour, a little longer if you plan a stop in the charming town of Spello on the way.

Day 9: Spoleto/Departure

It's a fair distance from Spoleto to the Florence airport, your point of departure. Depending on your comfort level with driving in Italy, allow at least 2½ hours to get there.

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