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There have been many contenders, but currently perched untouchably atop the podium of road trip competitors is Tuscany. I consider myself a bit of a driving tour connoisseur, having motored through almost every state in the mainland U.S. and all but a few countries in western, central, and eastern Europe. My top criteria for road trip nirvana are all met in Tuscany: smaller roads, little traffic, eye-popping vistas around every corner, and one after another enchanting hill town just often enough to get out and stretch the legs.

Our own little corner of the Tuscan countryside lies just outside the small town of Casole d’Elsa; like many other communities in the area, it’s a medieval hamlet up on a hill with a stone fort, narrow winding streets, and a variety of small shops, eateries, public buildings, and homes.

We can walk there from our pastoral lodging … or not. The Tuscan landscape encourages relaxation and just being, and we spend plenty of time with a bottle of wine, a few snacks, and a view of layered hills covered in spring flowers.

When we do stir, we have a panoply of other towns to visit, and first up is Volterra. A walled city of Etruscan origin, Volterra retains its city gates, an acropolis, and the foundations of ancient temples from that era, as well as the usual Roman ruins. We visit right after breakfast and ascribe our unanimous election of Volterra as our #1 hill town, in part, to that fact. There are few crowds, the town is spotlessly clean and well-cared for, and the views from the main piazza are swoon-worthy. We very much get the sense that the town belongs to its residents; while catering to tourists through shopping (mainly alabaster, the city’s chief product) and eating venues, Volterra feels very “real” and unperturbed by the infusion of visitors.

We leave Volterra by mid-morning for San Gimignano, a town we have very high hopes for given its uniqueness as the setting of multiple high towers that erupt from the rolling Tuscan knolls. Our anticipation builds as we pass a whimsical red sculpture encircling a view of the hills and, later, get a sneak peek at the walled town and its pillars from afar.

As we approach the triple-walled city (also from Etruscan times), we get our first inkling that this is no Volterra. We start to see large tour buses winding up the last few kilometers to town. We pass crowded parking lots and wonder why people are parking so far away. We inch closer in order to drop at least my parents at one of the main gates but fear we may never find them again amid the growing hordes of visitors.

San Gimignano has eight gates, a fact that will soon play a role in our small family group getting separated from each other. We end up parking in one of the lots we had just pooh-poohed and allow son T to walk into town while my parents and I wait for a shuttle bus. Big mistake. T enters the city at a different gate than the one we are dropped at, and we all, in our separate parts of this tourist madhouse of a town, wonder how this will all play out with no means of communication.

The two groups decide on their plans: our group of three takes the easy route and plops right down at a table near the main city gate and orders lunch. Group 2, the impatient T, ponders. He stays put for fifteen minutes at his gate, wanders nearby for another quarter hour, has a dawning of comprehension about the relative immobility of Group 1, then hightails it through the city to what he guesses is the main entrance. He is correct, and he finally approaches, panting and hot, just as lunch arrives. Disaster averted, but we’ve had an unlucky start in the Manhattan of medieval Tuscany.

Unlike its larger neighbor, Volterra, San Gimignano actually feels much busier and more populous. It is later in the day, and even the sleepy-headed tourists are up and out now, so part of the bigger feel here is likely due to the visiting crowds. Nevertheless, the architectural uniqueness adds to the big-city impression. From about 1200 AD on, San Gimignano became the site of two centuries’ worth of competition between its wealthiest families, with these rivals striving to build ever taller tower houses. By the end of the Medieval period, there were some 72 of these stone skyscrapers, and 14 of them remain today.

As we leave town after a long and crowded stroll, we question whether we should try to squeeze in another city visit today. Oh, hell … my parents are only in their mid-eighties; we might as well make them walk another few hours today! But really, there is no arm-twisting involved, and we set off for the largest place of the day: Siena.

As we enter the town, the streets are not crowded, and the tourists seem to have left for the day. We easily find a parking garage that says “Cathedral Parking.” Great luck – the church is, in fact, our main target this afternoon! We begin to walk in the direction of a few other people and marvel at our good fortune to be here at such a quiet, peaceful time.


Until we realize there really should be more people. And that the 5-minute walk Google maps has over-confidently promised us has now been going on for more like 12-15. We blame it on my mom and her slow-but-steady pace. Like many mothers, she is regularly accused of dallying, too much window shopping, not paying attention to signs, and anything else delaying progress, but she is actually not at fault today. No, it appears we have simply parked at the very far end of the city, and as we wend our way closer, other visitors do materialize, and we finally find ourselves in the large square in front of Siena’s imposing black-and-white striped cathedral.

We are too tired to really enjoy it. My dad finds it garish, and the rest of us think it’s okay. We are impressed with the stacking of the black and white marble to heights that seem unimaginable in the days it was built, and we very much like the chairs that are available for us to sit on. After a few minutes of taking in the now-familiar Catholic furnishings, we gather the energy (and my worried wits) to go back down (the slippery marble stairs with no handrail) into the square for another short rest before making the lengthy walk back to the car.

It’s been an exhausting day, but we make the short drive home and rally with a Tuscan toast. A plate of cheeses and breads, a bottle of very local red (right from the property), and a Vernaccia from San Gimignano are appropriate refreshments for the early evening, and we sit on our patio overlooking the hills we’ve driven all day. Tomorrow is another day in paradise, and we have no agenda. Either way –  eventful or unhurried – we all find Tuscany to be the star of the trip.