Tuscany itinerary: Seven days of hilltown gems

A vacation blueprint for spending one week exploring the great hilltowns of Tuscany & Umbria

Cortona—Gubbio—Perugia—Assisi—Todi—Chiusi—Montepulciano
Pienza—Montalcino—Volterra—San Gimignano

Day 1 - Cortona

Where to spend the night
Hotels in Cortona (day 1)
Hotels in Gubbio (day 2)
Hotels in Perugia (day 3/4)
Hotels in Assisi (day 4)
Hotels in Montepulciano (day 5)
Hotels in Montalcino (day 6)
Hotels in San Gimignano (day 7)
Make your way to Cortona, whose hilltop perch hides paintings by Signorelli and Fra’ Angelico and whose valley is peppered with Etruscan tombs.

Lunch in the countryside at Il Falconiere.

If you have time before dusk, climb past the vegetable gardens to the shattered fortress at the top of the ancient walls for a view that stretches as far as Lake Trasimeno to the south.

Have a light dinner at La Grotta and spend the night in Cortona.

Day 2 - Gubbio

Don't forget to pay attention to the "Before you Leave Home " box at the end of the itinerary covering all the details you need to take care of before leaving home—and be sure to read the "Foolish Assumptions" page about how these itineraries work along with more time-planning tips.In the morning, take the side road toward Lisciano, where you get on the SS416 over the Umbrian border to Umbertide. Switch here to the SS219 for Gubbio, a stony border town at the edge of a deep, wild range of the Apennine mountains.

If you like views and short hikes, take the cable car up Gubbio’s mountain and then climb the short distance to the top to explore the ruins of an old fortress and the wooded slopes surrounding it.

The best dinners in town are at the Taverna del Lupo, after which you can wander the streets to see the illuminated medieval buildings before turning in for the night. Spend the night in Gubbio.

Day 3 - Perugia

The SS298 leads to Perugia, now a city and the capital of Umbria, but still full of hilltown character.

Take the day to wander its superb painting gallery and visit its churches—including a converted pagan temple that is the oldest church in Umbria.

You can also check out the underground streets of the medieval city, preserved in the 16th century to serve as bastions for a fortress.

Perugia has one of the best passeggiata evening strolls in Italy, a few hours of which do wonders to work off a meal from one of its excellent restaurants before heading to your hotel for the night. Spend the night in Perugia.

Day 4 - Assisi

Head out early for a side trip to Assisi across the valley. After admiring the frescoes by Giotto and other trecento masters in the Basilica di San Francesco, you can either scale the medieval alleys to the well-preserved fortress above or take a countryside hike to St. Francis’ old monastery halfway up the wooded mountain.

Have lunch outside the walls at La Stalla, one of Umbria's best country trattorie.

You can spend the night here in Assisi or cross the valley back to Perugia to spend the night.

Day 5 - Todi, Montepulciano

Drive to Todi to pass the morning in this quintessential Umbrian hilltown from the Middle Ages with its High Renaissance temple just outside the walls.

After lunch at the Umbria restaurant, get on the SS79bis to the SS71 north. After 42km, branch onto the SS146 through Chiusi to Montepulciano.

This is one of the biggest of the hilltowns, full of life and Renaissance palace facades, and with streets so steep that most are cut with steps.

The wheezing climb to the top of town is worth it for the small painting gallery and hulking Duomo.

If you can manage another short climb, the bell tower on the civic palace flanking the cathedral offers a wonderful view on clear days.

After your workout, find somewhere to crash and spend the night in Montepulciano.

Day 6 - Pienza, Montalcino

If you didn’t make it to Sangallo’s perfect Renaissance church outside Montepulciano’s walls—a foil to the one in Todi—see it quickly in the morning.

But leave by 11am so you can make it to nearby Pienza to see its central piazza, the epitome of Renaissance city planning, and find picnic fixings for lunch.

During riposo drive to Montalcino, where you can spend the afternoon enjoying their beefy Brunello red wine inside the ramparts of a medieval castle. Spend the night in Montalcino.

Day 7 - Volterra, San Gimignano

Before you leave home:
 Book plane tickets
 Book hotels
 Check train times
 Learn more about Italy
 Practice your Italian

Drive past Siena to Volterra to pass the late morning and early afternoon communing with the Etruscan urns in the archeological museum and peeking in at the early 15th-century frescoes in San Francesco church.

Also take a gander from the panoramic promenade at the Roman ruins below town, but get to San Gimignano by evening to enjoy the Medieval Manhattan emptied of tour bus crowds.

Spend the night in San Gimignano and see as much as you want of the town, its towers, and its heavily frescoed main church the next morning. (OK, so technically this is a seven-and-a-half day trip.)

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This article was written by Reid Bramblett and was last updated in August 2010. All information was accurate at the time.

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