There’s something quite special that makes your head turn when a vintage Fiat 500 drives down the street in Italy. Their cute design, the nostalgic and romantic feeling of how things used to be and romantic thoughts of everything that comes to mind when you think of Italy; la dolce vita, Sophia Loren, country roads lined with cypress trees and intimate picnics in olive groves. I always feel the need to photograph these beautiful ‘Cinquecentos’ when I see them and I think that I would actually like to own one (even if just for the ease of parking in central Florence).

When Dragonfly Tours invited me to take part in one of their private tours of Italy, I was pretty excited, especially when they told me that I would be going on a Chianti Tour in a vintage Fiat 500!
Dragonfly Tours personally design unique trips to Italy for individuals or families, taking care of every last detail. From the moment you leave home, your private concierge will not only help you move around like a local but be there to assist with every experience, transfer, language barriers and anything you may have during your holiday. Every itinerary that Dragonfly tours create is tailor-made to satisfy individual needs and requests.

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Waking up to a gorgeous day of sunshine after what had seemed like weeks of rain prior, I knew it was going to be a special experience. I walked with an extra skip in my step that morning while enjoying the first feeling of Summer in the air as I headed to our meeting point in the busy Sant’Ambrosio neighbourhood. I was a bit worried about driving one of these vintage beauties around the busy centre of Florence because you have to hit the clutch twice when changing gears. (In Italian this is called the ‘doppietta’ ), but I needn’t have worried as Dragonfly Tours had thought of everything. Committed to providing only the highest level of service to their clients, my private guide approached, escorted me to a waiting luxury car with an English speaking driver who then drove us out of the city towards the Chianti region of Tuscany. Around forty minutes later, we arrived at the location where our gorgeous cars were waiting for us! I then met Giancarlo, my trusty driver and guide for the day who kept me entertained with his local knowledge and stories about each place we visited.

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Our first stop was the lovely, tiny village of Castellina in Chianti, which as you know if you have read my blog, is one of my favourite of the Chianti towns. It’s fascinating underground walkway, local trattorias, history and, of course, its castle makes it one of those quintessential Tuscan towns that you must visit. Of course, arriving in a vintage Fiat500 made the experience so much more special than usual.
After our little tour, we were back in the cars and headed to our next stop which I was pretty excited about as I had heard Giancarlo say that magic word, ‘degustazione’ – yes that’s right! Wine tasting!
It was mid-afternoon when we turned into the winery and the sunlight hitting the vineyards provided perfect picture-postcard photo opportunities. Once again, I was really happy that I wasn’t driving and was able to take photos, look out the window and admire this stunning Tuscan land. Upon arrival at the winery, we were led to the terrace where a table was set out and here we enjoyed seven different wine tastings, starting with a few whites including a Vermentino before moving on to some really great Chianti Classico reds including a Super Tuscan. Pecorino cheese with aged balsamic, bruschetta with extra virgin olive oil and salami accompanied our tasting and I could have sat here until the sun set, the location and view were just so idyllic. But no, our tour wasn’t over yet and I was happy to once again climb aboard my little car and head out through the vineyards. Another reason I was happy to have a driver was that I was able to really enjoy every glass that was part of my wine tasting. When on holiday, the last thing you want to worry about is not being able to drink because you have to drive, especially if you are tasting incredible Chianti Classico wines!

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After all that wine and savoury food, it was time for something sweet and Dragonfly Tours took me to a gelateria that I had never been to before but now that I know where it is, I will definitely be returning! I chose a new flavour and my usual; lime & basil for the new and pistachio, my favourite which I just can’t seem to pass up. The lime & basil was incredible and I would travel there again just for another taste!

As the golden hour approached, we arrived at the medieval borgo of Monteriggioni, famous for its original 13th-century architectural features including its fortified surrounding wall and its annual Medieval Festival. We arrived at the perfect time avoiding the busy midday tourist crowds. After a casual stroll around the town, and as the sun started to set, it was time to enjoy the last drive in my little Cinquecento as my tour was coming to its end. I said goodbye to Giancarlo, took a few more photos of the beautiful vintage cars and then climbed aboard my luxury car to be escorted back to Florence.

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The tour was beyond my expectations! The unique private tour experience made me feel like I was being taken around the Tuscan countryside with a friend. The cars had no flashy logos on the sides and so it seemed like I was out for a drive in my own car. I certainly felt very special and thanks to Dragonfly Tours, I got to experience and taste everything that I love about Tuscany.
I must admit I was sad to say goodbye at the end of the day. Having a local private driver was truly one of the best ways to experience everything you imagine Tuscany to be and more!