A Road Trip through Tuscany

Tuscany has always conjured up romantic images of golden-hued landscapes, with its rolling hills and cypress-lined roads. I had a mind to just jump in a car and drive--see what we stumbled across. As a result, I put much less planning into this portion of our Italian adventure than the Dolomites, taking a more on-the-fly sort of approach. As a result, I discovered that things like tours of renowned wineries book up very quickly and needed to have been reserved well in advance, and I know there were some picturesque spots, particularly in southern Tuscany, that we missed. But sometimes it is nice to just go with the flow--feels an appropriate state of mind for the wine-rich, sun-soaked, pastoral Tuscan countryside.

Siena

Siena was our first stop on the drive down from Florence. As with other towns with historical city centres, cars aren't permitted in the old town, so we found a parking lot outside the city walls. As it was nearly midday, the heat was oppressive, so I was eager to find an indoor activity. We made our way through the cobblestone streets, bustling with tourists, to Siena Cathedral. This medieval church, dating back to the 12th century, is quite the masterpiece of Romanesque-Gothic architecture.

The striking black-and-white striped marble interiors is quite unlike any cathedral I'd been in. They apparently symbolize the black and white horses ridden by Siena's legendary founders, Senius and Aschius. The floors were highly ornate, inlaid marble mosaics depicting scenes from the Old Testament, allegories, and virtues. Despite the throngs of people, the sheer size of the cathedral ensured they were suitably dispersed. It becomes easy to ignore the masses when you are staring up at awe-inspiring frescoes and stained glass windows.

A particular highlight was the Piccolomini Library, adjoining the main cathedral, which houses a collection of illuminated choir books. Floor-to-ceiling frescoes and elaborately painted panels depict the life of Siena's favourite son, Enea Silvio Piccolomini, who would go on to become Pope Pius II.

After we'd had our fill of religious monuments, we made our way through the winding streets back out of town, stopping briefly to see Piazza del Campo, considered one of the greatest medieval squares in Europe. It was nearly empty, as the blazing sun was bringing its full force to bear, with people seeking shaded sanctuary along the edges of the square (which in this case is actually shell- not square-shaped).

San Gimignano

About an hour's drive west from where we were staying lay San Gimignano, a walled, medieval town known for its 14 towers, of varying heights, punctuating its unique skyline. My excitement mounted as I drove up the hill, only to be quickly dashed when I realized I would have to deal with the practical realities of visiting a very popular destination in the Tuscan countryside and the madhouse of tourists that entails. I dropped off the parents at the city gates and spent a good 30 minutes driving to different parking lots, queuing to enter, only to discover there were no longer any available spots my car would actually fit in. I eventually found a free little parking lot down the hillside and hiked back up to town.

After a quick lunch, we walked up the main drag, lined with restaurants, tourist and artisan shops, flogging their wares. One that caught my mother's eye was a leather shop, Le Torri. She'd been inspired by the purse I'd brought, which discreetly houses my Sony camera, and had been searching for a leather purse in which she could put her own large camera. We were helped by a friendly saleswoman, who happily showed us a number of different options. Mom found herself a fetching purse, and I spotted a beautiful, hand-crafted satchel, made from the same kind of leather used for saddles (I'd been on the lookout for a respectable work bag since I started my job, and this more than fit the bill). Even Dad managed to find a small, over-the-shoulder leather bag to replace his somewhat bulky, belt-mounted pack.

Laden with our leather goods, we headed up to Piazza della Cisterna. Here, we had to join the rather lengthy queue to sample gelato from Gelateria Dondoli, which has produced world champion-winning gelato. We were almost lured in to the other gelateria in the square, with prominent signage claiming to be world-renowned, but some quick research set us right. Dondoli's gelato was very delicious--they even had a Thai mango and sticky rice option, which was superb.

Val d'Orcia

While the surrounding area near our AirBnB was rocky, verdant, and filled with vineyards, I was eager to take a drive south in search of the iconic Tuscan landscapes—golden fields, winding roads lined with cypress trees, and stunning sunsets. So we set off one fine afternoon towards Val d’Orcia.

One of our first stops was Bagno Vignoni, a small village known for its thermal hot springs. Just a short walk from where we parked were small canals of hot springs running from the main square and off the nearby cliff. Folks were just lounging on the ground, their bare feet dangling in the hot water. The views of the surrounding hills, dotted by farmsteads and villages, were also impressive.

Pienza

From there, we drove in the direction of Pienza, enjoying the seemingly endless rolling hills and patchwork quilt of fields and farm plots overlaying the landscape. We happened upon a stunning view, looking back at Pienza, bathed in the warm glow of the setting sun, as well as the distant hills in darkening shades of blues and greens.

I'd read about an ideal spot to watch the sunset and so somewhat frantically drove the winding roads to a hilltop, overlooking the valley below. We managed to arrive just in time to watch the setting sun, sparking a riot of colours against the thin clouds. While our time in southern Tuscany was very brief, just a long afternoon, it provided enough of a glimpse to whet my appetite for a return-visit some day.

Castles and Chianti

For our last day in Tuscany, we didn't venture too far afield, as there was plenty to see close to our little villa. Just 7 minutes away was Castello di Brolio, dating back to 1141. The castle has withstood assaults through the centuries, including artillery shelling during the Second World War, and as a result has had to be rebuilt in many places. This may account for the interesting mixture of architectural styles, from medieval to 19th century. The castle and its associated vineyards, have been in the hands of the Ricasoli family for the last 800 years, making it the oldest winery in Italy.

The interiors of the castle weren't open, but touring the grounds was plenty picturesque--especially the sweeping views of the Tuscan countryside from atop the battlements. I couldn't resist having a bit of a "Rapunzel" moment (as Dad likes to call it), perched at wall's edge.

We happily explored the courtyards and traipsed along the castle walls. After the crush of more popular spots like Siena and San Gimignano, it was blissfully quiet here, and we enjoyed having the place nearly all to ourselves for a time. The price of admission to the castle also included a free wine tasting in their wineshop. Never one to pass up free wine, I happily sampled Ricasoli's selection, grabbing a bottle of tasty white wine to take back home.

Radda in Chianti

There was soon a desire for gelato, as there was most days, and since we had some time to kill before our evening wine tour, we made a pitstop in a fairly random small town, Radda. It turned out to be an utterly charming spot, with a beautiful walkway outside the walls surrounding the old town that overlooked the surrounding hills and vineyards. We stopped at a produce stand to pick up some fruit for the road and got to experience a slice of local life, with its passionate Italian conversations and vibrant personalities.

We wandered through narrow streets, peeking into the artisan shops and wine stores. Despite being a small village, seemingly off-the-beaten path, there were still a surprising amount of tourists, though mercifully much quieter than Siena and San Gimignano. 

Badia a Coltibuono

From there, we made the winding drive, along narrow, tree-lined roads, to Badia a Coltibuono. Formerly a monastery dating back to 1051, it was owned by Benedictine monks until the 1800s. We were a little bit early for our tour, so we had time to explore the courtyard and beautiful garden (where Mom found perhaps the largest zucchini we'd ever seen at several feet long).

Badia a Coltibuono

Our friendly tour guide took us and an American couple through the winery, down into the cellars and through the family's private wine collection, housing untouched bottles from the 1930s. We then sampled four red wines (mostly Chiantis, given the region). Now my red wine knowledge is relatively minimal, but it was still entertaining to try to taste the nuances of the different wines. I particularly enjoyed the "Cultus" wine, which is more difficult to find internationally, so I grabbed a bottle to take home (my suitcase was starting to fill up with bottles of wine, which I suppose is how any return trip from Italy should be).

Sleeping & Eating

A highlight of our time in Tuscany was the lovely, 2-bedroom house (our little "villa") in the countryside, where we stayed for 3 nights. Set at the end of a gravel road, adjacent to a larger villa amidst woods and vineyards, it was a secluded, idyllic spot. The two-level home was very spacious--full kitchen, roomy living room, and one of the largest master bathrooms I've ever been in. It was definitely a place I would've happily spent weeks enjoying.

La Gorgia Vino & Cucina, Gaiole in Chianti

One of our favourite meals, perhaps of the entire trip, was at La Gorgia Vino & Cucina, in the small town of Gaiole in Chianti, not far from where we were staying. We sat outside at tables that were essentially in the street, sipping our wine and watching the small shops close up for the evening. The food was really outstanding--flavourful, inventive, and beautifully-presented. We started with risotto, which was finished off in a hollowed-out round of pecorino cheese, along with phyllo-wrapped delights drizzled in a cheese foam. Next up was pork tenderloin as well as rooster, stuffed with pork, in a pesto sauce. Just superb!

Osteria di Brolio, Gaiole in Chianti

Before visiting Castle Brolio, we stopped in at Osteria di Brolio at the entrance to the estate for a spot of lunch. It was a large restaurant, with a spacious patio, and we were visited frequently by what seemed to be the neighbourhood cat, who stared up at us longingly and was repeatedly shooed out the door by waitstaff. Mom kept things light with a mushroom salad with ham, and I couldn't resist mushroom pasta. Dad flexed his culinary horizons again and tried roasted pigeon for the first time (and quite enjoyed it!).

La Bottega del Nobile, Montepulciano

For our dinner in southern Tuscany, we stopped in at the hillside town of Montepulciano. It was after dark when we arrived, which was a shame, as I've read the views from the town are stunning (well, something for next time!). Nonetheless, we needed sustenance before making the hour-long drive back north to our AirBnB, and La Bottega del Nobile came well-reviewed. We started with a cheese and charcuterie board, the highlight of which was a chicken liver paté stuffed in a croissant (divine). Dad enjoyed sea bass, while mom sampled local pork cheek. I could never resist ravioli stuffed with pecorino cheese. We finished things off with a sumptuous dessert: chocolate done several ways (chocolate and orange brownie, chocolate and hazelnut sponge, and a ganache). Our culinary adventures in Tuscany were nothing if not decadent.

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