19:17 – Chiocchio: approximately 15km south of Florence

At a crossroads, our guides Matteo and Andrea are laying out our final option for the day. “From here we have two choices: we can take the flat road back to Firenze or the climb back up to Chiocchio for a spectacular view of the sunset”.

We all look at each other. I decide to start the decision making process, “well if it’s going to be a nicer view, then maybe the climb would be worth it..?” Matteo smiles “OK then, that’s decided. The climb to Chiocchio it is”. The group looks at me. It seems that I have decided for everyone. Now I really hope it’s worth it…

08:00 – Rolling Dreamers HQ: on the outskirts of Florence

It is July, an already glorious morning of bright sun and we are gathered to hear what the day ahead holds. We already know it is a road ride (mainly, more about that later) of around 130km. Most of us already have the route shared via Komoot on our Wahoos so there are no surprises on the distance for the amount of climbing involved.

We will be taking in the best that Chianti has to offer – ‘how do they define what makes Chianti wine anyway?’ I wonder to myself, making a mental note to later ask one of our guides. They outline what we can expect from the day ahead. Today is one of their more advanced options. They tell me they also offer shorter routes with or without guides and van support. Though the distance may be daunting for some, we have the van as an option. Not that anyone would necessarily want to consider it right at the beginning. But it’s good to know it’s there.

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Cycling in textbook Tuscany

For those who have never visited Tuscany, it often exists as a kind of filmic pastiche; a cliche of sunny days over vineyards, stone houses and cypress-lined avenues. Some people visit only Florence and call it done but we are here to see as much as one can in a day on two wheels. The idea is to get deeper than the obvious and for such a goal, one needs local insight. We have that in the form of our guides, with their combined decades of experience riding on and off road all around Florence.

They amicably chat about cycling in Italy, their experiences of Iron Man triathlons and famous cycling events. The walls of their office are adorned with race numbers and photos showing what, for most of us, would be a Bucket List of cycling experiences: Eroica, Nova Eroica, Strada Bianche, Maratona dles Dolomites, Roubaix… the list goes on. As we are here to ride and not just talk about riding we saddle up and get ready. However, as any dedicated Instagrammer knows #ButFirstCoffee.

We set off from the office to seek out a quality Italian coffee – no rushed espresso shots for us. Weaving through pedestrians and past book stalls, antique markets and locals already laden with supplies for lunch we arrive at La Ditta Artigianale. There they take us through the finer points of coffee: the beans, the growing, the selection and roasting, the different methods of production… This is as thorough an insight one could hope for and makes us appreciate the final product all the more. Certainly better than an over-priced cappuccino in the city centre. The ex-convent that houses this branch of La Ditta (there are two others in the city) has a serene atmosphere, the refurbishment of the space is clearly a labour of love and this fact is confirmed by the owner Francesco who informs us that it was four years in the making.

Once caffeinated we depart. The first few kilometres through the city give us a feel for our bikes: 3T Exploro Race models with Pirelli’s latest road bike tyres. The cobbled streets are an indication of how the bikes react to uneven ground even as we carve our way through the Florence.

A side note here: the city has been working hard over the past decade or so to make more cycling infrastructure and also to reduce the number of motorised vehicles in the historic centre. The result is a limited traffic zone that makes navigating the city by bike much less hectic than many other Italian cities.

We start to head upwards and reach the wondrous view of Florence from Piazzale Michelangelo; it’s a must-see and of course, pretty soon we are all stopped taking photos: of the view, of the bikes, of the bikes and the view…. 

The climb to Impruneta is the first proper uphill – the 50m elevation gained to Piazzale won’t get you many bragging rights – and serves as an introduction to the rolling Chianti hills. Our route is challenging but the gradients rarely go into double digits. The kilometres fly by but there is some disagreement about the bikes. Everyone has their own opinion on whose bike has the best colour scheme.

We agree to disagree and around us the palette is all-Tuscan: the deep green of the vines and the carefully controlled colours of the houses which seem to be as natural a part of the landscape as the wild flowers growing by the roadside.

No ride in this area would be complete without some Strade Bianche – the typical Tuscan white roads. This is gravel riding of the most soulful kind, some would say it is the home of gravel cycling. Way before the professional circuit included a race here locals were hammering themselves on their old steel steeds along the dusty backroads.

Our bikes are much more forgiving and one can only wonder at those heroes on their skinny tyres. Indeed Eroica translates as Heroic and it’s easy to understand why. We continue and the speed barely declines as the road surface switches from asphalt to gravel and back again. I get the feeling that this is exactly what these bikes are for; just one ride here would convince anyone.

On the route, we pass through well known places like Greve In Chianti with its picturesque town square and lesser-known places like Vertine, a tiny walled hamlet perched on top of a hill. By the time we arrive in Gaiole In Chianti, the home of Eroica, we feel that we are starting to get an inside view of Tuscany, helped along by the ever present guides and their cheerful insights. 

They are most cheerful as they talk about some of the more fearsome climbs in the area; ones that we will fortunately not be tackling today. “There’s one of there that goes over 20 percent!” We get the feeling they would rather enjoy introducing us personally to these Tuscan walls or “muretti” as they call them.

The furthest point from Florence is Gaiole In Chianti where there is time for a quick visit to White Roads – the “Bottega Eroica” to peruse the many items of clothing and accessories, all of which are designed and made by the owner. I want to buy everything. But we have a long way back. Matteo reminds me that we have the support van. He doesn’t realise I could easily fill the van with my purchases, so I take a card with the website on it instead. 

After a traditional Tuscan Panino (not ‘a panini’ as Andrea points out: panino is the singular, panini being the plural of two or more) we set off for our ride back in the gorgeous afternoon glowing light. The vineyards are becoming familiar now. The way the land is divided, with vines on the lower slopes and wilder, unkempt forest higher up is incredibly photogenic but the light is starting to fade. And so we eventually arrive at the crossroads where I become the unwilling decision maker on behalf of the group. 

Over 100km in the legs at this point we are all feeling the distance and the elevation but the knowledge that it is the final push takes us over the top. When we arrive there it is, incredibly, even more spectacular than what has been before as the vineyards open on both sides of the road and the valleys are bathed in the golden hour light. Matteo grins at me and I have a feeling that this was his plan all along and I merely served as his stooge. This hill, at this moment, is a perfect way to finish off a perfect day in Tuscany. And from here the last 13km are downhill; it doesn’t get more perfect than that. 

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