Italy’s Great Hill Towns

In this program, we'll drive through the Tuscan and Umbrian countryside connecting all the hill-town dots, see a ceiling fresco masterpiece not by Michelangelo, eat rustic bruschetta, walk a vineyard that goes all the way back to Etruscan times — and more, all while exploring a string of hill-capping medieval towns that somehow manage to keep their heads above the flood of the 21st century.

Travel Details

Orvieto's Cathedral

Orvieto's duomo has Italy's liveliest facade. This colorful, prickly Gothic facade, divided by four pillars, has been compared to a medieval altarpiece. The optical-illusion interior features some fine art, including Luca Signorelli's lavishly frescoed Chapel of San Brizio.

St. Patrick's Well

Modern engineers are impressed by this deep well, designed in the 16th century with a double-helix pattern. It's a total of 496 steps up and down — lots of exercise and not much to see other than some amazing 16th-century engineering, though an audioguide available onsite provides interesting background.

Tenuta Le Velette

For a short tour of a historic winery with Etruscan cellars, make an appointment to visit Tenuta Le Velette, where Corrado and Cecilia Bottai offer a warm welcome (but be sure to call ahead). Their wines are considered to be some of the best in the region.

Giovanni Adreani

High-energy Giovanni exudes information and is a great guide for anyone home-basing in Cortona with limited time and an interest in Tuscany's highlights. Giovanni takes up to five people in his car to Montepulciano, Pienza, Montalcino, and a winery for a tour and tasting; he also offers tours in and around Cortona ([email protected]).

Abbey of Monte Oliveto Maggiore

Five miles south of Asciano, this Benedictine abbey features perhaps the best in-situ art you'll find in rural Tuscany. The order spared no expense in decorating their main church, importing the great artists of the day: Fra Giovanni da Verona, one of the most talented inlaid-wood artists who ever lived, and the skilled fresco artists Luca Signorelli and Il Sodoma. What you see today is very close to what a pilgrim would have seen during a 16th-century visit. It stars an astonishingly detailed inlaid choir, and a cloister frescoed with vivid, detail-and-symbolism-packed, sometimes outlandish scenes.


See the Travel Details above for recommendations highlighted in bold, excerpted from Rick's guidebooks.

Hi, I'm Rick Steves, back with more of the best of Europe. It's springtime in Italy and while it's a little early for grapes, it's a perfect time for exploring the hill towns. Thanks for joining us.

Connoisseurs of Italy find the quintessential charms of this country in its characteristic hill towns. Built on hilltops for defensive purposes in ancient and medieval times, today their lofty perches seem only to protect them from the modern world.

We'll drive through the Tuscan and Umbrian countryside connecting all the hill town dots, admire a ceiling fresco masterpiece not by Michelangelo, eat rustic bruschetta, visit a vineyard that goes all the way back to Etruscan times — and more, all while exploring a string of hill-capping medieval towns that somehow manage to keep their heads above the flood of the 21st century.

So many European travel dreams feature Italy. And in Italy the regions of Tuscany and Umbria are home to the greatest hill towns — all within easy striking distance of Rome or Florence. In this episode, we visit Civita di Bagnoregio, Orvieto, Cortona, and, finally, San Gimignano.

Many of this region's hill towns date back to Etruscan times — well before ancient Rome. Others date to the fall of Rome. When Rome fell, Europe was engulfed in chaos. People naturally grabbed for the high ground to escape the marauding barbarians that characterized those Dark Ages. Over time, these towns were fortified and eventually functioned as independent city states.

In their glory days, they proudly charted their own course...generally free from the dictates of popes or emperors. Then, the bubonic plague swept through Tuscany in 1348. That, combined with the increasing dominance by the regional bully, Florence, turned many bustling cities into docile backwaters. Ironically, the bad news of the 14th century mothballed these towns, leaving them with a unique charm and a tourism-based affluence today.

Siena maintains much of its medieval character. Its sprawling main square and towering City Hall recall the days when it rivaled even Florence.

Assisi — with its walls, gates, and castle — was home to St. Francis. Its massive basilica remains a favorite destination for countless pilgrims today.

Volterra was an Etruscan capital centuries before Christ. Within its wall, the town's rustic center offers an evocative Tuscan charm.

And San Marino — all 24 square miles of it — is unique in that it's still an independent country. While novel today, tiny two-bit dukedoms like this were once the norm.

Medieval Italy — like most of Europe before the rise of modern nation states — was a collection of independent little San Marino–style city states — many of them no more than fortified towns on hills.

While each of those hill towns are famous and very touristy, the explorer who gets off the beaten path can still discover hill towns with much less tourism.

A good example is Civita di Bagnoregio. Perched on a pinnacle in a grand canyon, the traffic-free village of Civita is, for me, Italy's classic hill town.

Entering the town, you're enveloped in history. Passing under a 12th-century arch, you enter another world. Every lane tells a story.

On the main square, the church marks the spot where first an Etruscan temple, and then later a Roman temple, once stood. Ancient pillars from those pagan temples stand like giants' bar stools in front of the latest place of worship to occupy this spot.

For me, exploring a town like Civita is a cultural scavenger hunt. There are countless towns like this throughout Italy with similar subtle charms. A fancy wooden door and windows lead to thin air. This was the facade of a Renaissance palace — which fell into the valley riding a chunk of the town's ever-eroding rock pinnacle. Pondering the view, you're reminded that, slowly but surely, this town will succumb to the march of geological time.

Civita is adapting to the modern world. As its permanent population dwindles, it's becoming a weekend escape for wealthy urbanites. The families that stay are catering to visitors.

To enrich your experience, be an extrovert: Poke around…talk to people.

Woman: Buon giorno. Piccolo, la molle bello, bello! [Little squishy one, so handsome!]

Maurizio: Come, Rick, I want to show you my mill.

The olive mill Maurizio's grandfather once ran is now the centerpiece of his restaurant…and he's happy to tell me how grandpa made the olive oil.

Maurizio: All the olives come from the valley. When they have about 200 kilograms of olive, they put here the olive, and with a donkey, they start the press for about two hours of hard work. When the paste is ready, they put the paste inside this filter, and when you have about 15 or 20 filters full, you are ready for the press. And then when the filter is ready, you can make the first press. You put the stick here and you make hard work for about two hours. You press and you wait. You have a good extra-virgin olive oil and you're ready for a big bruschetta.

A good bruschetta is simple: bread toasted over the coals…garlic, tomatoes, salt, and oil. Enjoying a rustic bruschetta is a fine way to cap a visit to a rustic village like Civita di Bagnoregio.

Orvieto, Umbria's grand hill town, sits majestically high above the valley floor on a big chunk of tufo — a soft and easy-to-cut volcanic stone.

A handy funicular shuttles visitors from Orvieto's train station and big free park-and-ride lot on the valley floor up to the town.

More and more European towns are dealing with their traffic and parking congestion by making life frustrating and expensive for anyone who insists on driving into the old center. Public transit is designed to reward those who park outside of town.

From the top a bus connects with the funicular and drops people right at the cathedral square. Pedestrian-friendly lanes make exploring the town a joy. Inviting shops show off Orvieto's famous and colorful ceramics.

The cathedral — or duomo, as they say in Italian — gets my vote for Italy's liveliest facade. This gleaming mass of mosaics and sculpture is a circa-1330 class in world history — back when no one dared question "intelligent design": Things start with Creation. Eve is tempted by Satan disguised as a snake, and so on, right up to Judgment Day.

Inside, the striped nave appears longer than it is. That's because the architect designed the nave wider at the back and narrower at the altar. Windows of thin-sliced alabaster bathe the interior in a soft light.

Adjacent the altar, the Chapel of St. Brizio is Orvieto's one must-see artistic sight. It features Luca Signorelli's frescoes of the apocalypse. The vivid scenes depict events at the end of the world, but they also reflect the turbulent political and religious atmosphere of Italy in the late 1400s.

The nearby city of Florence had become a theocracy run by the austere and charismatic monk, Savonarola. His ultra-conservative teachings polarized Christians, bringing tension to the Church.

In the Sermon of the Antichrist, a crowd gathers around a man preaching from a pedestal. It's the Antichrist — representing Savonarola — who comes posing as Jesus to mislead the faithful. This befuddled Antichrist forgets his lines mid-speech, but the Devil is on hand to whisper what to say next. His words sow wickedness through the world from a corrupt woman taking evil figures running mass executions.

Then, on Judgment Day, trumpeting angels blow a wake-up call, and skeletons of the dead climb dreamily out of the earth to be clothed in new bodies. Across the chapel, the saved gather happily in heaven enjoying a holy string quartet. Facing them, the damned experience the horrible mosh pit of Hell. Devils torment sinners in graphic detail, while winged demons control the airspace overhead. A demon turns to tell his frightened passenger exactly what he's got planned for her.

Signorelli's ability to tell stories through human actions and gestures, rather than symbols, inspired his younger contemporary, Michelangelo, who meticulously studied Signorelli's work.

Orvieto, with its natural hilltop fortification, was the pope's place of refuge in the 1500s. He wanted to be sure he had water during a time of siege. So he built an extravagant well.

St. Patrick's Well — 175 feet deep — is designed with a double-helix pattern. The two spiral stairways allow an efficient one-way traffic flow — intriguing now, but critical then. Imagine if donkeys and people, balancing jugs of water, had to go up and down the same stairway.

Digging this was a huge project. Even today, when faced with a difficult task, Italians say, "It's like digging St. Patrick's Well."

While the town is busy with tourists during the day, Orvieto is quiet after dark. The back streets feel oblivious to the crush of modern-day tourism. Evocative lanes seem to keep the mystery of the Middle Ages alive. Locals are out savoring their town with an after-dinner stroll.

I find restaurateurs are happy to let me cap my meal by taking my after-dinner glass of Vin Santo to a favorite spot to enjoy the magic of a hill town after dark.

The countryside of Umbria and Tuscany is velvety green in the spring. Fertile fields are set off by venerable estates and cyprus-tree-lined windy lanes.

Before moving on to our next hill town, we're stopping by the Tenuta Le Vellete vineyard to sample the most famous product of the region — the Orvieto Classico wine.

The Bottai family is happy to show thirsty and prospective customers around their estate.

Corrado: So, this is our farm that belongs to our family since six generations, and at our feet, we have a lot of history coming from the Etruscan times.
Rick: I can imagine.
Corrado: A good area for making wine because of the volcanic soil just in front of the view of the beautiful town of Orvieto. And if you like, I can take you to the vines to show you.
Rick: I would like that.
Corrado: So this is our soil, a volcanic soil, very rich in minerals, on which our vines grow and produce our Orvieto Classico wine. So this is a little bunch –
Rick: Yeah.
Corrado: — that would be ripe in September. It starts now to grow, and we'll pick it in six months.
Rick: And in how many years until that is actually drunk and enjoyed as wine?
Corrado: We'll drink this wine in 18 months, and we'll go on drinking this wine for two more years.
Rick: So how long have people been making wine right here?
Corrado: People have been making wine here since the Etruscan times. Twenty centuries.

And the family house has a history nearly as rich as the vineyard.

Cecilia: You know, Rick, this house is very old. The very central block was a control tower that was built in 1000. Then, when the tower got destroyed, the monks Premonstratensi took the place; they renovated it and made it a monastery. And my family, in fact, bought this property in the middle of the 1800s, and they re-renovated the whole building according to the style of that period. And so the frescos you have now, they are dated 1800-something.
Rick: So this is all Romantic from the 19th century?
Cecilia: Yeah, absolutely. This is the piano room, and my great-grandmother loved to play the piano. And this is a piano that Franz Liszt used to play.
Rick: Franz Liszt played this piano?
Cecilia: Franz Liszt played this piano several times.
Rick: I've got to try it. Can I try it?
Cecilia: Please.
Rick: Oh, my goodness.
Cecilia: My pleasure to listen to you.
Rick: Hmm. It's not Franz Liszt, but he might enjoy that.
Cecilia: So come on Rick, I take you to our secret place, the secret cellar. The little door and the cellar where the Etruscans used to store their wines. And this is 500 meters long, and was started to be carved 500 B.C. by the Etruscans.
Rick: So this is all dug out of tufo stone?
Cecilia: Yes, and this is perfect for aging the wines, and the Etruscan people knew that. And tufo has the perfect conditions to age the wines in terms of humidity and temperature. And modern wine makers are trying to duplicate the same conditions, and this bottle of wine is more than 30 years old.
Rick: More than 30 — ? Is it still good to drink?
Cecilia: It is absolutely wonderful to drink.

I've been bringing my tour groups to the home of Cecilia and Corrado Bottai since their parents were running the place. When I see the new generation taking over, and Cecilia pouring the family's wine into my glass, I feel the pride the Bottais have in sharing the fruit of their heritage and hard work with a visitor from so far away.

With a few bottles of Orvieto Classico in our trunk, we're ready for more hill towns. Crossing from Umbria into Tuscany, our next stop is Cortona.

Cortona has a history that goes back 2500 years to Etruscan times. It grew to its present size between the 13th and 15th centuries, when it was a colorful and crowded city. It was conquered by the regional powerhouse Florence, and eventually absorbed into its realm.

When Florence took over Cortona, its captains ruled the city from here, the Casali Palace.

Back then — like today — occupation was a thankless task, and every six months or so Florence would have to send in a new captain. When the new captain arrived he would establish his rule by putting his family coat of arms into the building's wall.

These date from around 1600, and were once colorfully painted. The medallions, like much of the city, were made of sandstone, and suffer badly from erosion.

While Cortona is extremely popular with Americans lately, its gritty personality survives.

My friend and fellow tour guide, Giovanni Adreani — whose family goes back seven centuries in Cortona — is joining us.

Giovanni: Many people from US, many Americans, they know Cortona because of the modern novel, Under the Tuscan Sun, but actually, for us, it feels different. It does feel different because it's been 200 years that we have people living in Cortona, foreigners. That romantic view we have about Cortona is about people from France, from England staying in Cortona. It was the grand tour.
Rick: So this dreamy idea we have about Tuscany, it's really 200 years old? Created by the French and by the English?
Giovanni: By the French and by the English. It's a romantic view that they made.

Giovanni: So this is what I mean as a romantic view onto Tuscany. This terrace is made by the people here, time of Napoleon, for enjoy the view of Tuscany, the valley.
Rick: They made it for the tourists.
Giovanni: Yeah. By the way, that's Umbria. Where you see the lake and the hills, here was the border of the Holy Roman Empire. You know Charlemagne? He was until here. And there was the state of the pope. So the Umbrians, they were under the pope for centuries, until the 1800s. But all over Italy is like this: divided. Every hill, every valley, another culture, and so we have many Italys.

The memorial bust of Giuseppe Garibaldi, the brilliant revolutionary and hero in the struggle for Italian unification, enjoys this same view. This is a reminder that uniting the many cultures of this peninsula was the main challenge the fathers of modern Italy faced back in the 1860s.

Via Nazionale, while only named in the 19th century to celebrate Italian unity, has been Cortona's main drag for a long time.

Giovanni: So this is the corso.
Rick: Yep.
Giovanni: It is the main street.
Rick: So people are walking. Passeggiata.
Giovanni: Yeah, because it's easy, it's flat. By the way, the real name is "Via Nazionale," but we call this road "Rugapiana" — that means "flat wrinkle."
Rick: The flat wrinkle?
Giovanni: You saw the other alleys, you know.
Rick: So this is really the only real flat road in town?
Giovanni: It's the only flat road we have.

And sooner or later, those strolling end up on the main square under the old City Hall. The mayor flies three flags: Europe, Italy, and Peace. Tuscany is famously left-wing and pacifist.

For a more contemplative peace, head for one of Tuscany's many evocative monasteries. The Benedictine Abbey of Monte Oliveto sits remote yet bold. While tranquil today, you can imagine the power monasteries like this must have wielded in centuries past.

The fine 500-year-old frescoes lining its cloister shows scenes from the life of the founder of the order, St. Benedict. Benedict established the first monastic movement after the fall of Rome. By filling the political vacuum left by the demise of the Roman empire, he planted the seeds of Europe. For that, today Benedict is considered the patron saint of Europe.

Visitors attending the daily Mass find the monastery is still very much alive with the monks worshipping as they did in centuries past: in Latin with Gregorian chants. This timeless music adds yet another dimension to the vibrant cultural landscape and culture of central Italy.

Our next stop is named for a less-famous saint, Gimignano — or, in English…Gimignano.

San Gimignano, with its distinctive skyline, stands like a medieval mirage on its hilltop.

About midway between Siena and Florence, San Gimignano was a natural stop for pilgrims en route to Rome. Its walls were built in the 13th century. Its mighty gates regulated who came and went. Through the Middle Ages a steady stream of St. Peter's-bound pilgrims stoked the town's economy.

This was a pilgrims' shelter — one of 11 in town. The Maltese cross indicates the building was constructed by the Knights of Malta...perhaps the medieval equivalent of a Rotary Club project.

Today, tourists replace pilgrims — and it can be really crowded. The locals may seem fixated on the easy money of tourism, and much of this old-looking architecture is actually faux medieval — reconstructed with a flair for the fanciful in the 19th-century Romantic age. But San Gimignano's so easy to visit and visually so beautiful, it remains a good stop.

Piazza della Cisterna is named for the cistern that supplied this old well. A clever system of pipes drained rainwater from these rooftops into the cistern built under the square. This has been the center of the town for a thousand years, and it's still the place to hang out.

San Gimignano's claim to touristic fame is its striking towers. Of the original 60 or so, about a dozen survive. Before there were effective walls, rich people fortified their own homes with towers like these. They provided a handy refuge when ruffians and rival city states were sacking the town. Prickly skylines like San Gimignano's were the norm in medieval Tuscany.

In the 14th century, San Gimignano's good times went very bad. About 13,000 people lived within the walls. In 1348, a plague decimated the town, cutting its population by two thirds. A crushed and demoralized San Gimignano fell under the realm of the regional bully, Florence. To make matters worse, Florence redirected the vital trade route away from San Gimignano.

And Florence required that most of the towers be torn down. The town never recovered, and poverty left it stuck in a 14th-century time warp. That explains San Gimignano's popularity with tourists — and its prosperity — today.

The hilltowns of Tuscany and Umbria offer a rich assortment of travel thrills. From dramatic settings to exquisite architecture, and from the rustic traditions of its food and wine to its hospitality, this region has all the elements that make travel to Europe forever fresh and rewarding.

I hope you've enjoyed our visit to some of Italy's unforgettable hill towns. Join us next time for more of the best of Europe. I'm Rick Steves. Until then, keep on travelin'. Ciao.


Not by Donatello but by…

In 1348 a plague decimated the community, cutting its population by two-thirds. It's really bad, two-thirds, imagine that.

…a plague decimated the community, wiping out about two-thirds of its surly population.