Taking Tuscany by foot

On the way to San Gimignano. Photos by Simon Cunliffe.

James Bond made it look easy. There he is at the outset of Quantum of Solace jumping into his Aston Martin in an unnamed exotic location and moments later stepping out in the Piazza del Campo in Siena.

True to form, he times his entrance to maximise the confusion and the visual impact in the middle of one of the most dramatic, but short-lived spectacles in the Italian cultural calendar.

The celebrated Palio - a thrilling, feverishly partisan horse race around the cobbles of the angled and tight-cornered Il Campo square - has featured in Siena since the Middle Ages, many centuries before 007's modern producers, in search of ever more exotic locations, contrived to place the spy in the midst of the twice-yearly, 1min 40sec event.

In mediaeval times, you arrived at Siena at a more leisurely pace and made your entrances a little less arresting.

This fascinating Gothic city stood on the pilgrimage route between northern Italy and Rome.

Mainly you travelled by foot, or horseback, along the trail, sections of which still exist.

Intermittently during our six-day stroll through the Tuscan countryside, we join the Via Francigena, today a network of dusty tracks hosting those who prefer to get a little closer to the land - replete as it is with culture and history - than is possible from car or bus.

In the embrace of a late-summer heatwave that has gripped Italy with the clammy intensity of a Berlusconi sex scandal, you tend to work up a little more of a sweat than the ever-cool Daniel Craig.

But for those who have come as well to sample the irresistible delights of Tuscan cuisine, and the local wines, the exercise is an excellent counterbalance to the inevitable ballast taken on board with a procession of meals, each seemingly more delicious than the last.

Knowing where to join the trails; which of the profusion of trattorias, ristorantes and pizzerias in the enticing Tuscan towns offer genuine value-for-money culinary treats; how to take in the culture without overdosing; what grapes and which wine labels to enjoy; and learning the history of the region and the countryside but without feeling as if you've joined either a school field trip or a queue of tourists all clutching the same well-worn guide book requires a degree of local knowledge.

As our guide, Brett Naisby, puts it with his trademark wit, the trial-and-error acquisition of that knowledge means "you end up kissing a lot of frogs".

Naisby, a Canadian, is married to New Zealander Eve Hope, a ceramics designer based in Tuscany, and together they spend four or five months a year based in Christchurch planning their next season's itineraries.

He can claim at least honorary Kiwi status.

It is partly this connection and partly felicitous word-of-mouth recommendations that have seen us break the habit of a lifetime - a diehard preference for DIY travel - and sign up for one of their Customwalks tours.

But back to the Piazza del Campo in Siena and its breakneck pulsating bareback ride.

Having hiked for a few hours on each of the four preceding days, we have earned an entire day off for shopping and sightseeing, and Naisby has conjured up a local expert to show us the ropes.

"They even wanted to put James Bond in the race itself," explains Rita, with a degree of disdain as if such a feat were impossible even for the celebrated secret agent, "but we refused".

She shrugs with pride, which is evident again as she takes us into the contrada, or quarter, of the town whose horse won the last Palio.

The symbol of the owl adorns the red and black flags that drape throughout the quarter, demanding renewed respect from the rest of the Sienese, and months of bragging rights.