No matter who you speak to – whether they live in Italy, visited Italy or even heard about Italy – San Gimignano is on the top of the list of places to visit in Tuscany. And I now join this long list of fans, for San Gimignano is one of the prettiest towns I’ve ever seen. But I jump ahead. Let’s get back to our journey.

We are excited, nervous, anxious but most of all rearing to go as we pack up our cycle gear and leave Volterra – the Tuscany valley ahead – our dreams of cycling through its most famous towns finally coming true. We have decided, in the interest of flexibility of time, to opt for a self-guided tour as offered by Saddle Skeddadle. You are pretty much left on your own, given details of your journey, accommodation in each of the towns is pre-arranged, your luggage transported as you meander along at your leisure from city to city. I mean how difficult can this be, right?

S T O P ! – our self acclaimed leader shouts from the back of the group – We’ve missed the very first turn. Now, picture this. We are a group of wanna-be cyclists, who have ‘trained’ for this vacation, and are traveling down hill with the wind in our hair and smiles on our faces. You can imagine therefore that the thought of stopping and turning around uphill, is not very appealing – to put it mildly. We stop, we deliberate, our leader takes one for the team and retraces our tracks.

Minutes and minutes go by as we wave to passers-by who are probably wondering why we’ve decided to take a break on the corner of what has turned out to be a very busy road. We wave none-the-less pretending that this is part of our plan. Our leader returns and we are finally relieved to learn that we are on the right track. Smiles once again confident that we can do this, and we are on our way.

The day passes without another hitch. We amble through the recently harvested fields of wheat, stop for much needed refreshments (Prosecco and beer, of course) along the way and quietly skirt through the small towns and villages along the way.

It’s a tough first day of 36km – the sun is hot, the undulating terrain challenges our new found cycling skills as we are faced with an uphill stretch of 12km at the very beginning. One or two of us take our first bike spills, and, did I mention that the sun is hot. We are undaunted however. We laugh through it all as we continue our exciting journey.

We arrive in San Gimignano, sun scorched, starving, discussing the day and as we push our bikes through the welcoming arch we are left speechless – not because we are exhausted but oh my, this place is priceless – the quaint streets, unusual shops, towers, the charming square – warm our hearts and we are immediately relaxed. The challenges of the day immediately forgotten.

We are happy, exhilarated and most importantly triumphant. One day down, four more to go. We celebrate with Prosecco and pizza and, as the sun sets, we are surprisingly entertained by street musicians in the main Piazza.

Smiles are back on our faces and we look forward to another glorious day.