Chasing 15th Century Hill Towns Using 21st Century Technology: A Drive Through Tuscany

by Steve Smith

People often tell me that good travel is all about the journey, and the destination is irrelevant. While that’s true in a philosophical sense, and it’s the major reason why I travel, there is no journey without a destination. To try out the latest way of getting to that destination, I was equipped with a portable Global Positioning System (GPS) on a recent trip to Tuscany.

This relatively new navigation system, fast becoming a staple with automobile owners, came loaded with video and voice systems to guide me through the Italian countryside, an area around Florence, plus informative talks by my electronic tour leader, e-giovanni. Accompanied by my other co-pilot, otherwise known as my wife, I was able to navigate my way with ease through this land of fields and vineyards to its famous hill towns and less traveled pockets.

For this electronic marvel, we can thank the Renaissance genius Leonardo DaVinci, whose contributions to science and technology included breakthroughs in navigation. Some point to evidence that his knowledge of celestial navigation was derived from texts by the Chinese. And many believe it was the Arab civilization in the tenth century that laid the foundation for his remarkable works. Living in a desert environment with clear night skies, the Arabs combined the astronomical legacy acquired from their Babylonian neighbors with homegrown navigation techniques of their own. Arab merchants had passed along both the tools and the knowledge to their Italian trading partners well before DaVinci’s time.

Naturally I was concerned that even with this new marvel, I might not cope well with Italian drivers. I’d heard the stories about their chariot-racing gladiator heritage along with jokes that driving in Italy is a contact sport. I found these stereotypes far from the truth. Sure, Italian drivers can be aggressive. Some consider a stop sign to be discretionary, and frequently they’re bumper-biters. But since I’d grown up in Southern California, where the car is king and the road trip is a rite of passage, it was only a natural progression for me to take the wheel here as well.

But driving was only part of this adventure. Could I navigate using GPS? Or would I find myself lost and stranded after following directions from this device without question?

Luckily all this had been handled beforehand with written backup directions that accompanied my GPS unit. For added peace of mind, a cell phone call to Giovanni (the non-electronic one) was possible for help in the event of any unforeseen problem. However, I found that using a GPS was as easy as operating an ATM machine, and I never needed to use that mobile shoutout. When I followed the touch screen menu and selected a destination, a route was calculated that led to the best hill towns and scenic cypress-lined country roads. Even the narrow one-way city streets to the town hotel or parking garage weren’t a problem. And if I felt adventurous and elected to drive independently off the tour route, the GPS would chart an alternate course back to my original destination. It was that easy to find our way to my five favorite destinations in Tuscany, which I share with you here (in no particular order).

Siena, the town everyone loves. Although the herd doesn’t typically sway me, I vote with the majority on this choice. Make sure you budget at least two full days to cover this UNESCO world heritage site. Walk these medieval streets in any direction and drop into everyday life while sampling the many flavors of gelato and pan forte. For a true slice of life, spend an evening at the Piazza del Campo and watch the moonrise over the brick plaza, Siena’s front porch.

Montepulciano is probably best known for the famous wine of the same name. While this city is pedestrian friendly and traffic free, it’s most friendly to those with strong legs, as its topography emphasizes the “hill” portion of hill town. Visit its medieval churches and palazzos, but realize that they stand over a foundation of ancient Etruscan ruins. Ask to visit the wine cellar of just about any enotecha to descend into this subterranean world.

Spoletto is a perfect introduction to small town Italy. Take some time to explore the medieval cobblestone lanes and drink in the local ambiance. A must see is the archeological museum, a restored Benedictine monastery which encompasses a Roman theater as well as Roman and Etruscan artifacts.

Le Crete Senesi is an area of superlative drives. Just south and east of Siena, Road 438 traverses a rollercoaster series of clay hills coated with vegetation whose colors morph with the seasons.

Bevagna has everything a hill town has to offer but the hills. Walking here is the opposite of in Montepulciano, since very little is vertical and nothing’s more than 10 minutes from anything else. Take a stroll and have the residents show you their town. Just ask.

And one parting thought: Although all vacations must end at some point, the journey never really does. The memories of good travel remain even as the trip fades and our dreams propel us foreword to the next one.