We are repeat offenders.  Our modus operandi is to go to the same places over and over again.  While it’s been years since we’ve traveled this road – close to a decade in fact, when Miss P was just a toddler and Miss V not even a thought – we have been here before.  It is a road with white knuckle turns, and with winds and twists that will have you alternating curses with prayers as you move the car ever closer to the edge to ensure that the road-hogging vehicle barreling toward you at top speed can pass.

For those, who like me, have issues with motion sickness, SS222 will leave your head spinning and stomach churning, but it is a small price to pay for what you find along this stretch of road: wine. And lots of it. SS222 or Via Chiantigiana, takes you through Tuscany ’s wine region and it is in the wineries in this tiny area of Italy that the famous Chianti wine is produced.

While we wanted to discover wines from a new winery or two, we also planned to stop at a couple of our favorites from the previous trip to purchase wine: Enoteca di Fontrutoli and Castello di Verrazzano.

117 of Castello di Fonterutoli’s 650 hectares of land are divided between 5 specialized vineyards: Fonterutoli, Siepi, Badiola, Belvedere and Caggio. These wines are available to taste and purchase at the Enoteca di Fonterutoli, just steps from the castle and vineyards. The estate also produces olive oil and cultivates lavender used for a line of cosmetics.
A 10th century tower looms over buildings from the 15th and 16th century at Castello di Verrazzano, the birthplace of Giovanni da Verrazzano, a name many may know from the bridge named for him (minus one “Z”) in New York.  The castle welcomes visitors, but you need to call ahead.  For those doing this drive on a whim, like we did, you can purchase wine at the punta vendita (sales outlet), just be sure to check the opening hours.

We chose to take this excursion – from the farmhouse near Siena where we were staying through the Tuscan wine region – on Prima de Maggio (May 1), which is a national holiday, so most of the wineries were closed.  Although a little disappointed, we were not defeated, because having traveled this road before, we knew about a wine cellar in Greve in Chianti.

Le Cantine di Greve is Italy’s oldest wine cellar, and offers more than 150 wines available to taste by the glass at any time, even on Prima de Maggio!  The cellar uses the Enomatic system and has a multilingual audio guide offering commentary for those wanting more information on the various wines.  Le Cantine also sells platters with variations of cheese, salami and bread allowing you to sample the wines with food.

I was happy to see that Le Cantine has managed to maintain its charm, while also keeping up with the times. The 500 year-old cellar now sells merchandise, including wine parphenelia, t-shirts, region specific travel books and has a Facebook page and a Foursquare account, a must in this age of social media.

Of course, I “liked” the page and checked-in while I was there.

As we sampled a number of wines, trying to decide what, in addition to Castello di Verrazzano and Castello di Fonterutoli, we wanted to purchase, we decided having the car was a curse and blessing. A curse because we had to relay on the spittoon more than we would have liked, and a blessing because we could buy a couple of cases to put in the trunk to bring home.

After making our purchases and loading up the trunk, we went around the corner to a little pizzeria we fell in love with on our first visit to the town.  Though the pizza is very good, and I would recommend the place to anyone going to Greve in Chianti, there are probably many other pizzerias in the area that are just as good.

But being repeat offenders, I doubt that we’ll ever know for sure.

Do you go to the same places over and over again, or do you seek to cover new ground?  Tell us the places you’re happy to revisit.