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 de 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 de 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 de Bagnoregio.