Travel /
Toscana

Wild Boars, Stolen Peaches, and the Long Road from Florence to Siena

“I decided, somewhat impulsively, that it would be a fun idea to walk from Florence to Siena. […] It all sounded very bucolic.”

 

August in Florence is a notoriously languid time. Restaurants close up shop, residents decamp to the sea, and the streets are deserted save for red-faced tourists. It’s too hot for anything other than drifting from shadow to shadow very slowly, while sipping cool sparkling water. It’s not, ordinarily, a time to set off on a three-day hike into the Chianti hills.

 

Nevertheless, a couple of summers ago, I decided, somewhat impulsively, that it would be a fun idea to walk from Florence to Siena. It would be some 50 miles between the two renaissance capitals along the historic Via Chiantigiana. Without too much persuasion, I recruited a brand-new friend called George to accompany me. Our plan was drawn up over bowls of spaghetti and an ill-suited map: for three days, we would walk through sparkling valleys and empty alabaster paths, sleeping on riverbanks of sage and stealing wild peaches. We circled pit stops at Greve-in-Chianti, Montefioralle, Panzano and Castellina. It all sounded very bucolic.

 

DAY 1

Strada in Chianti, Greve in Chianti, and Feeling Thirsty in Chianti

 

We set off at 5 a.m. that August morning, the streets dark and cool as we climbed out of Florence in the half-light. At dawn we came to the village of Grassina, and, pleased with our progress, decided to go off-trail along a dried-up riverbed to Strada in Chianti. Along that dusty path, we passed olive groves and overhanging peach trees asking to be stolen from. We were full of excitement, and as we were still in the earliest stages of our friendship, happy conversation kept us going for the whole morning. 

 

We found Strada in Chianti still asleep in the late morning, the heat already creeping in. The town’s squat, concrete houses had little historic beauty after Florence, so after a quick cappuccino and a re-pack of our tiny bags, we followed signs to Greve in Chianti. We climbed and climbed in a mirage of heat through more vineyards and rolling woodland, passing boarded up hotels and a hilltop monastery, but absolutely nowhere to fill our water bottles. 

 

By lunchtime, the heat was buffeting and our moods were darkening. We’d covered nearly 16 miles before reaching Greve in Chianti, where we collapsed in a typical Tuscan osteria in the central piazza. Here we ordered giant platters of pappardelle with wild boar ragu, cured salami and deep-fried coccoli dough. Fresh watermelon followed and for the moment, our heatstroke abated. 

 

At six o’clock, we filled our water bottles and made for the hills again in the golden evening light. On the grounds of a deserted masseria, we found a resting spot among parched olive trees. We assembled a small kindling fire on an old stone well cover and cooked some salty fat sausages we’d picked up in Greve, threaded onto barbed wire. I foraged blackberries and grapes while George assembled a makeshift spit, and we appreciated the romance of the moment. The dry embers burnt out before the sausages had even cooked through, but we ate them anyway. Despite the magic of it all, that first night under the stars was full of uneasiness.

 

DAY 2

Hitchhiking and Cinghiale, Dead and Alive

 

Around 5 a.m. the next morning, a hoarse, devilish cry jolted us awake. Without a word, we briskly packed up our bags and walked, in our pyjamas and under the light of the moon, to find some form of civilization. As we crossed a farm track, the shadowy figures of a herd of wild boards charged suddenly in front of us. Cinghiale–the creatures of yesterday’s sausages and pasta sauces–were rather terrifying in real life. The intimate chit-chat from yesterday was gone, and when I tentatively asked if George thought the howling could have been a wolf, he didn’t reply. The day continued in the same sometimes amicable, sometimes crotchety silence. We were thirsty, and idle conversation had to be kept to a minimum.

 

The option of hitchhiking hovered temptingly in the air every time a car slowed to look at us, two sweaty Brits with New Balance trainers and silly Swedish bookbags. The first time I saved George from the brink of a tantrum was when I flagged down a bewildered German couple, who took us the final mile or so up a particularly dull stretch of main road. Later that day, noticing me floundering in the unbearable afternoon sun, George repaid the favour and hailed a local farmer, who assumed we were looking for the restaurant nearby. We were, as it turns out: it was one of the simplest and best meals I’ve ever eaten. First came bread and home-pressed olive oil, bitter and verdant, still green from last year’s harvest. Then a milky burrata–oozing like gloopy white paint–alongside cool melon, basil and prosciutto. More pasta, perhaps an ice cream, a crisp glass of cold white wine. As we sat in the dappled vineyard, overlooking a vegetable garden, we marvelled at the ingredients, the perfection, the colours and the fragrance; harmony was restored. How lucky we are, we said, to taste and live and feel this moment. And how strange to share it with each other.

 

Replenished, we took the liberty of a siesta on some picnic benches. That night, after a couple more miles, Siena felt almost within grasp. A derelict farmyard presented itself as our bedroom, and we settled in the ruins of a strange lumberjack hut. The broken wooden floorboards felt like luxury, and I busied myself with domestic tasks like sweeping the millipedes away and lighting citronella candles.

 

Conversation flowed, and George told me about his sisters, his parents, his thoughts on God. Once again, I had the sense of a friendship accelerated by our poetic surroundings, the mundane washed away by the open road. The same heightened senses applied to the food we found–the berries and cherries and sticky fat grapes. Dinner was dry paninis, accompanied by Ennio Morricone cello music, washed down with the scarce water supply. More wild boars returned that night, scuffling around in the dry bushes, and the irony of having eaten their siblings was not lost. George found a large stick and blunt knife to keep by our bedsides and I fell quickly asleep.

 

DAY 3

Fluffy Robes and Victory Dinners

 

On that final day, Siena came into view. We took to the road once more for the last leg of our journey, hobbling through the ochre city walls in the late morning. A little delirious, we checked ourselves into The Grand Hotel Continental. Here, we were rewarded with lemon sorbet, a cold shower, and a victorious dinner of even more wild boar, this time slow-cooked. The cool atrium of the historic hotel may never have been more appreciated than by us two filthy travelers. We lounged all afternoon in fluffy robes, before enjoying a tour of their extensive wine cellar. After a summer in Florence, we’d recalibrated our senses and arrived somewhere more or less under our own steam. It was a joyous feeling. Nevertheless, as we agreed over pastries and fresh coffee at breakfast the next morning, we’d rent a Vespa next time.