There are several ways to blend in with the locals in Italy and simultaneously max out your cool points. Even if you don’t speak a word of Italian, buying a copy of La Gazzetta dello Sportwill imbue you with instant street cred for just one euro. Tuck its pink pages under your arm as you grab your morning cornetto and caffè – always consumed standing up at the bar – while sunglasses tilt at a jaunty angle on top of your head, whatever the weather.

As for getting from A to B, it has to be a Vespa, the waspish scooter that transports everyone from local priests to flirting teens and shopping-laden grannies. And now, holidaymakers.

Brett Naisby, a Canadian, has been based in Tuscany for enough years to know just about everyone in the small town of Gaiole-in-Chianti, and to speak Italian as much with his hands as his voice. He has offered walking and cycling tours for more than a decade, but has recently started three-night tours around the hills of Chianti on his fleet of seven red Vespas. They are aimed at weekending Brits who want to indulge La Dolce Vitafantasies with the support and back up needed for scooter virgins on the “wrong” side of the road.

This time, however, I was the token Englishman as we – three Australian women, one from Canada and another from California – cautiously got to know our lipstick-red machines in a car park, just down the road from Gaiole’s small, pretty piazza.

Everyone, including me, seemed rather nervous, despite the fact that the 125cc engine versions we were to drive are easy to operate and below the limit that requires a motorbike licence in Italy. My worries stemmed from the fact that the last time I was on something similar, 17 years ago in Indonesia, I drove straight into a wall in front of an entire village who just about died laughing. A bruised coccyx, a very bruised ego.

But now, there were no gears, just a push-button start, a throttle and front and back brakes. In fact, the hardest part seemed to be lugging it off its stand and then remembering to turn the indicator lights off after turning.

After about half an hour we were pootling – some more gingerly than others – along quiet country lanes in formation towards the hilltop village of Barbischio, Papa Naisby leading the way. I was aware, over my shoulder, that I was delaying a small car behind me as we headed towards the village of Castagnoli. As we passed pine trees and vineyards, I expected a scowl from the driver, but as the small Renault overtook, a pretty young woman smiled and waved as she pulled away.

Over the weekend, Italian drivers proved a pleasant surprise, never turning into their supposed Formula One-wannabe stereotypes, although some made generous use of both sides of the roads on corners.

That evening, feeling visibly more relaxed, we dined just outside Gaiole on the terrace of a small restaurant called Le Contrade, although two of the group had minor prangs getting up the gravel track. Just as well, with the red wine flowing, that we left the scooters where they were and walked back to our hotel, the quaint La Fonte del Cieco, up some stairs and tucked away in a corner of the town square.

On a typical day we would speed off (well, 25mph) after breakfast, stopping for a cappuccino in a village such as Lecchi, where the locals would gather round, pointing at the Vespas, recalling, I surmised, memories of way back when. (“Sophia! Phew! 1967, I think? What a summer!”) We buzzed through woods, by cypress trees, along fields of vines and olives, up and down hills of which sweaty, Lycra-clad cyclists seemed to be making heavy weather, to towns such as Radda. There we would explore the rambling lanes and invariably find our way to an ice-cream shop, before heading out again for lunch. Near Brolio castle, for example, at Il Carlino d’Oro, we had a simple, delicious meal of salad, tagliatelli with mushrooms, pana cotta, coffee and a glass of wine for £10 each.

A bargain – and we were the only tourists there. This is part of Naisby’s plan, sharing his favourite spots after 13 years in the area. We headed back to Gaiole in no particular hurry, having taken a stroll around the castle’s ramparts, and enjoyed some wine tasting on La Fonte’s terrace before dinner in the piazza.

Towards the end of the weekend two of the Aussies dropped out, preferring to go walking instead. “Perhaps I’m a slow learner,” said Karina Devine, “but I really wanted some more time to practise before we set out. If I went back, I’d walk rather than ride – being on the Vespas is a solitary way to tour. Having said that, I still consider these four days in Tuscany to be a highlight of my trip.”

Our dwindling group set off towards Siena under increasingly threatening skies. We cruised along the top of the Crete Senese, the area where the woods of Chianti give way to more rounded, clay hills, with large, open wheat fields that spread down over the horizon. In the small town of Asciano we stopped to observe a wedding before entering Siena, which seemed even more full of character (and empty of tourists) under a leaden sky that eventually spilt its rain just as we reached the Piazza del Campo.

On the way out of town we encountered our only really busy stretch of road of the whole weekend, which was unnerving given the traffic-free routes we had taken so far. Our arrival coincided with a traffic-surge caused by the end of a local football match. In trying to turn right from a side street, Elizabeth Brooks, our companion from California, tweaked her throttle a little too vigorously and almost skidded under the front wheels of a moving van, which screeched to a halt inches from where she lay.

“No experience necessary is one thing,” said Elizabeth, looking back and nursing a spiral fracture of her right ankle, “but leading people through rush-hour traffic wasn’t wise. Despite that, the weekend was fun. I loved the patterns of the rolling fields in all shades of golds and tender greens, outlined by the dark, green rows of cypress trees.”

Naisby has added extra information to the Scooterbella website setting out who he thinks the trip will and – perhaps more importantly – won’t appeal to. “We have found that most people who are over 45 and who have never ridden a scooter or motorbike have problems riding the Vespa,” he says. “If you have not used the ‘motorbike’ part of your brain before the age of 45, then it may be too late to learn – we just want everyone to have a happy and safe holiday.” Despite the Siena hiccup, I enjoyed myself enormously, whizzing from one glorious, calorie-laden blowout to the next. I’m not sure anyone ever mistook me for a real Italian, despite my best efforts on my lean, mean, little red pulling machine. If I can just master a few more hand gestures and groom the chest hair, though, I could be in with a shot.

Need to know

Scooterbella (01622 775222, www.scooterbella.com) offers three-night trips from £970pp from July to October. This includes use of the scooter, guiding, B&B stays, evening meals, and transfers from Montevarchi, but not flights.

EasyJet (0905 8210905 – calls cost 65p a minute, www.easyjet.com) flies from Gatwick and Bristol to Pisa from £43 return. Make sure your insurance covers you for riding a scooter. Helmets are compulsory and are provided by Scooterbella.

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