We stay at a farmhouse in the valley that spreads out north west of Cortona, in an apartment that is on two levels and has five-metre ceilings. There is a pool, a large dog, soccer balls, a restaurant and a few other children. Unlike our hotel in Florence, where the kids were either bouncing off the walls or watching Popeye cartoons in Italian, here they are let loose on the beautifully manicured, though still operational farmland (producing wine, honey and olive oil, among other things). My nine-year-old daughter plays with the dog and sits at a table outside the kitchen, making terra cotta figurines. My son plays soccer and runs around with 10-year-old Italian boys, oblivious to the age and language barriers. My wife and I sit in the beautiful restaurant, enjoying the local wine, eating too much, talking without interruption. In the five days we are there, I routinely see my son sitting in the laps of Italian women, utterly at home, absently eating pasta or biscotti, their perfume lingering in his curls when he returns to us.

The considerable logistics of cycling are taken care of by Courtney, the Florence-based American guide our tour company, Butterfield & Robinson, sent us. She arrives every morning in her van with an array of bikes, gear, snacks, maps, English newspapers and sound advice. Every contingency is dealt with: We are left simply to ride the well-planned, largely traffic-free routes she has mapped, to eat in the welcoming restaurants she chooses.

The next morning we drive to Cortona, home of Frances Mayes, author of Under the Tuscan Sun. “Perhaps you saw the film?” asks Giovanni, a local guide explaining the town’s layered history to us.

“No.”

“Thank you. It was very silly.” It was filmed here, joining the growing list of films that have used the area as a backdrop: The English Patient , Gladiator (the scene where Russell Crowe is dying and imagines his Tuscan estate, the entrance lined by cypress trees), Life Is Beautiful, Much Ado About Nothing. Mel Gibson was scouting film locations in Pienza. To some extent, the films have helped revive these towns and cities, refracting them through the seductive lens of Hollywood. The young, who had almost uniformly moved away in the 1970s, are now returning and renovating the centuries-old apartments. The area has become desirable, and increasingly expensive.

In a small chapel there is a large beautiful canvas done by Pietro Berrettini, a 17th-century Cortona artist. It is the familiar scene of Jesus languishing; behind him is an oversized cherub, a beautiful boy. Giovanni claims this is the cherub that started a post-Renaissance industry. “Ten years later, there are hundreds of fat happy children flying all about in Florence,” he says dismissively. “They are rolling around with lions.” Another trend, like so many, that got out of hand.

During the tour, Giovanni cites the considerable shortcomings of nearby towns. The extent of civic allegiances in Italy is always a surprise. The City-States that existed until the country was united in the 19th century still retain their hold. The Romans are decried as loud and self-important, still believing they are the centre of the world 2,000 years after the fact. The Florentines are reserved to the point of coma, and the Milanese aren’t really Italian. There are criticisms of other towns’ wine, olive oil, art, claims on history. A special enmity is reserved for the people of Pisa. A local saying states: Better a death in the family than a Pisan at your doorstep. To which the Pisani reply: May God grant your wish.

In the afternoon, we take a 39-kilometre ride from Cortona down through the valley, my wife and daughter trailing behind on their bikes, my son’s questions dimly heard in the rush downhill out of town.

“If you were bad, would someone cut off your head?”

“No.”

“If you were superbad?”

The olive harvest is in two weeks, and in Cortona, pickers comb the trees with wooden rakes while the olives are green. In the south, they spread nets and wait until the olives turn black and fall off. That method is much cheaper, but yields an inferior olive oil, another reason to disdain the neighbours.

We descend into the valley, a rare long stretch of flat road, going past the massive shells of abandoned 17th-century farmhouses. Here on the flats, near the highway, they are unlikely to be reclaimed as so many others have, by foreigners or urban Italians, and remodelled into elegant holiday palazzos. They will remain historic orphans. Above us, on a hill, two cranes labour over the renovation of an ancient estate that is surrounded by stately cypress trees.

On the road we run over a small green snake that is lying near a dead hedgehog.

“From Medusa?”

“Probably.”

A light drizzle begins as we make our way up a hill. A sign that shows an incline with an unsettling percentage beside it (13) comes into sight as the rain intensifies into a downpour. The climb is four kilometres long, the kind that crushes the spirit of Tour de France riders who, while going perhaps marginally faster than me, don’t have to answer a million questions about good and evil. As we crest hills that stubbornly go on, we discuss Medusa’s difficulty in making friends, why she didn’t have a family.

“How did she brush her hair?”

“With a special comb.”

“A bad comb?”

Outside of Trequanda, my family abandons their bicycles for the protection of Courtney’s van, which is waiting on the side of the road. I, feeling brave, trade my hybrid bike for a sleek racing machine that weighs less than my water bottle. It is a greyhound, a titanium threat, easily the coolest bike I have ever ridden. I continue up the hills, and finally reach the summit and begin the welcome, frightening charge down. I am taking a route past Torrita di Siena but find that the road, which I was on the day before, is not only closed, but effectively gone, disappeared under construction. I take the unevenly marked detour and head toward Bettolle, then take a wrong turn down a pleasant, unoccupied road that I thought would lead to the main road, but leads instead to a cornfield. It is 5:45 p.m., and the dusk is glorious, the light spraying through the clouds in singular rays, but I am at least 15 kilometres away from the farmhouse and will lose the light in half an hour. I am also still completely lost.

It is dark by the time I find a familiar road. I labour through the hills and look up at the inviting lights of the four-star Villa Petrischio restaurant where I have had a glorious guinea fowl dinner and a bottle of Brunello of such depth that it haunts me still. On the flats I crank the bike up as far as I can and glide through the dark. Lightning flashes over Cortona on the hill in the distance, like a special effect from a horror film. It is well after 7 p.m. when the farmhouse comes into view with the welcome relief of home, my children playing in the front with the dog, the table set.

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