We love to explore Italy on the roads less traveled. But sometimes, the back-roads are a bit more than we bargain for.

A few weeks ago we decided to drive to Montalcinoin southern Tuscany. We left at about 11 am, with the intention of getting there for lunch, taking  the Si-Fi superstrada, which means that Siena is at one end, and Firenze, Florence is at the other. We had no problem getting to Siena, but then inadvertently took a wrong turn. As the road curved along the south side of Siena the choices were to continue east, or head south. Since Montalcino is south of Siena, the choice seemed obvious. “Seemed” is the operative word.

Now, before I go any further, there’s something you need to know about Italian roads.

There must have been a jokester on staff when they installed signs on the Italian back-roads, because very often, they point in directions that can’t possibly be right. You’d bet any amount of money that it has to be a mistake because it just feels counter-intuitive. But then somehow, eventually, it usually takes you there. “Eventually” is the operative word here. We’ve turned around because we just didn’t trust the sign—only to find out later that it was right. Then of course, there are times when the signs actually have been wrong. That creates a bit of a dilemma—you have to decide: are the signs right or not?

This time, we were clearly on the wrong road as a result of our miscue. Rather than the #2 heading directly toward Montalcino, we were suddenly hurtling toward Rome on the #223! What??! Oh well, we’d just have to cut across to get back on track. But where? Our first try turned out to be a large driveway, and another choice dead-ended at a tiny village. We finally came upon a road through the town called Murlo which looked like it might work. We had to chuckle since we were trying to get to Montalcino, famous for its Brunello wine, yet having to go through “merlot”—a funny turn of events. However, our little bypass didn’t look like a big problem. Just a few short kilometers and we’d be back on track. Right. Wrong!

About half way across the new route, there was a sign pointing to Montalcino. We were faced with that same old problem: is the sign right or not? We decided to go with it. Turns out the sign was technically right, but failed to mention a few details . . . like  the countless twists and turns, or the more importantly, that it soon became an unpaved road. We almost turned back but it looked like a fairly short distance on the map (about half an inch), so we stuck with it.

We drove and drove and drove on what the Italians call a “white road.” Sounds quasi-romantic, right? They’re made of white-ish gravel and light colored dirt—hence the name. Hmmm. A little less romantic. They frequently sport countless potholes, wash-boarding and tricky ruts. Definitely unromantic!

But all was not lost, because after about 30 minutes on that dust-choked strada bianca we came upon an amazing sight. There in the middle of nowhere was a golf course! Now in August, Tuscany is mostly amber in color. With valuable water at its lowest level, we all wait for September rains. But there it was, in all of its majestic green-ness, as we motored along between the manicured fairways and immaculate greens with fluttering flags. It felt a bit surreal. There in the middle of the snakey white road and the sun-scorched hills was the 18-hole Castiglion del Bosco Golf Club!

Amused with our find, we continued on our way, thinking that Montalcino must surely be close by, otherwise who would ever find this oasis? As we slowly rounded blind curves, we encountered dust-covered . . . no, make that dust-encrusted black cars. Each one seemed to be going way too fast for the road conditions, but then again, it was around 1 pm. Tuscan lunchtime!

After roughly 45 minutes on the white road, we finally snuck up on Montalcino from the south west. I know, I know, we started out from the north.  We climbed out of the car and looked back over the valley that we had just crossed. It was beautiful (from this new vantage point), and we had finally arrived at our destination unscathed—one of the loveliest little Tuscan hill towns ever. We had a delightful lunch at Grappolo Blu and then headed out of town toward Pienza. Just as we got to the bottom of the hill, there was an ambiguous sign—pointing in the opposite direction from what we thought should be the right way. After our white road detour, we actually pulled to the side of the road to talk it over.

Then, throwing caution to the wind we decided to roll with the Italians no matter what, following their sign pointing in the opposite direction. After a delightful hour drive through the countryside on extremely smooth asphalt roads, we arrived in the equally beautiful hilltown of Pienza!

Posted on September 17, 2011