Explore: Florence with Rolling Dreamers

Three different and dazzling adventures around the Tuscan city of Florence in three days

This article was produced in association with Rolling Dreamers

Journeys never start when we physically set off. They usually begin much earlier, when we dream them up. All it can take is a glance at a map or a finger tracing a line drawn on a sheet of paper. For us cyclists, the desire to ride on new roads and in fresh places is a constant. And it can stem from a story told by a friend who has just been there, from a conversation overheard on the train, from a photograph that caught our eyes in the pages of a magazine – or from following a bike race on TV. For instance, watching the Giro d’Italia every day for three weeks for many years leads to an irrepressible attraction to a cycling adventure in the Bel Paese

According to the data collected by ENIT, the country’s tourist board, Italy is one of the two most popular destinations for cyclists from all over the world. (The other, unsurprisingly, is France, which has the most-watched televised sporting event in the world; no prizes for guessing its name.) Who hasn’t fantasised about visiting Tuscany, its white gravel roads and the Chianti hills around Siena after watching a stage of the Giro or the Strade Bianche from one’s sofa? We decided to make that dream a reality with three diverse rides, over three days in Florence.


For those who have never visited Tuscany, they may be familiar with the well-established cinematic cliché of blue skies, stone farmhouses, sun-kissed vineyards and long gravel paths lined with cypresses. “Some cyclists come to Florence to visit certain places they expect to see and our job is to make that happen. But as Italians and cycling enthusiasts, we also have the desire and pride to show those who ride with us that Florence and Tuscany are much more than what people already know.” These are the words of Matteo Venzi and Andrea Gelli of Rolling Dreamers, our guides for the next three days who have organised this cycling feast. florence siena by bike

Speaking of food and drink, a day on a bicycle in Italy can only begin with a coffee; in our case, it is a bar in the centre of Florence, set within the cloisters of a recently-restored former convent. In other countries, such a place would be a museum or a library; in Italy – and in particular Tuscany, which holds 11 per cent of the artistic and cultural heritage of all Italian regions – this use is perfectly normal.

Related: The best gravel bikes from Rouleur Live

At every turn in Florence’s alleys, we find a good reason to chat with someone or to take a photo. Every time we stop, chances are someone asks for details about our rides and where we are headed. That’s because Italy is a country of cyclists and the bicycle is a conversation starter. As we are about to leave the city centre, before crossing the Ponte Vecchio over the Arno river, we find ourselves in front of the breathtaking Cathedral of Santa Maria del Fiore. Built with white, green, black and red marble and completed in the 1400s, it is immense: 153 metres long, 90 metres wide and 90 metres high. We ride around it slowly and Matteo has his work cut out: “Let’s go! Today’s route is long, we’ll have time to enjoy riding in the city tomorrow.” It’s mid-morning: intending to do 130 kilometres, we have covered less than four.bike ride florence

The climb to Impruneta marks the first effort of the day and we are rewarded with a bird’s eye view of the city we’ve left behind from Piazzale Michelangelo, one of those world-famous vistas immortalised in many films. The gentler gradient is a welcome prelude to the rolling hills of the Chianti area. Along the way, we pass through well-known places like Greve in Chianti, with its picturesque square, and lesser known ones like Vertine, a village perched on top of a hill. Then it’s on to Gaiole in Chianti, the symbolic hub of the Eroica, the renowned granfondo that attracts many from every part of the globe. “Doing the Eroica on these gravel roads should be on the bucket list of any passionate cyclist, even with a modern bike,” says Matteo. 

The attraction of those strade sterrate is magnetic for us too; we can’t resist a few sectors at full gas. Unless you hit a particularly challenging sector, 28mm tyres are more than enough in most conditions. There is next-to-no traffic and anyone who travels on them is only there for the scenic route. Even the few travelling on motorbikes look ecstatic, despite being covered in dust. 

florence bike and food tour“Spring and autumn are the best times for a cycling holiday in Tuscany, but you can also have lots of fun in the height of summer,” says Matteo. With the help of the wind, even today’s temperature highpoint of 42°C is surprisingly bearable. After a sandwich and a cold beer, we visit Bottega Eroica, a shop with a wonderful cycling collection that could easily max out our credit cards. But we dodge financial disaster because, being on a bike, we can’t take our purchases home. “We can send them straight to your hotel in Florence,” Emanuele Nepi, the owner of the historic shop, tells us with a smile.

As we set off again, Gaiole marks the turning point of our excursion today. The late afternoon sun’s rays are not so fierce, and despite the kilometres and climbs in our legs, it’s still fun. Every now and then we hit a few short and steep ramps, the so-called muretti, or little walls, which in some cases have short sections with gradients approaching 20 per cent. The Chianti vineyards dominate the landscape around here.

florence bicycles

On the way back to Florence, we decide to detour via Chiocchio. The gently-rising road runs along a ridge with views of the surrounding hills and the scene is astounding in the softer evening light. Shades of yellow and orange envelop us. The return to Florence, on the valley road, already falling into shadow, turns into a kind of race finale with a friendly rivalry. We don’t know whether our motivation to go faster comes from enthusiasm for the excellent day we’ve had, the more bearable temperature or the desire to go to dinner. Perhaps all three together.


The Parco delle Cascine is a huge green space to the west of Florence and offers a perfect and peaceful way out of the city. There, the prevailing population consists of children on rollerblades, dog walkers and joggers. The park is closed to motor vehicles and we can ride side by side while continuing the conversations started during the sumptuous breakfast consumed earlier on at the Caffè dell’Oro near Ponte Vecchio. Diego, as always, reserves an outside table for the Rolling Dreamers’ cyclists with a priceless view of the historic bridge.florence bike holidayscycling tour florenceWe strike out west along the Arno, reach Montelupo Fiorentino and press on over the hills almost as far as Vinci, the birthplace of the Renaissance genius Leonardo. The hills of Montalbano are one of the lesser known areas of Chianti. We ride mainly on back roads, switching between off-road and tarmac. Swapping a road bike for a fast gravel bike was certainly the right choice. Along the Pesa river, we ride on a rocky embankment, where the trails are more demanding than yesterday and the heat here is more fierce. We emerge in Cerbaia, Machiavelli’s hometown and from there, after a short climb, we continue towards Chiesanuova, where we stop for a sandwich. “Here, they bake the schiacciate,” Matteo points out. For those who have never eaten one, it is a salty, stuffed focaccia, doused in Tuscan olive oil and fresh out of the oven. Enjoying one with a cold beer or a glass of wine is worth the price of the entire trip alone. 

“In trips organised for our customers, some of the main priorities are the food and the places where we stop for a break. What we aim for is not just refuelling breaks but real moments in which the pleasure of riding is mixed with the pleasure of experiencing Italian life, good food, the historic places we pass through and people’s company,” says Matteo. florence bike tour

Near the end of our ride, we meet Valerio, the owner of a roadside watermelon stall on the southern outskirts of Florence. “The King of Watermelon” is how Matteo introduces him, shaking his hand and hugging him, while we prop our bicycles against a roadside wall. “His watermelons are the best in town,” he says. It would be rude not to try a few big slices of cold, freshly-cut produce. We patiently fumble with our knives to remove the seeds and chat, enjoying the fruit while sitting at the side of the road by some folding tables, sheltered from the sun. Is there a better way to end a summer day on a bicycle?


The climb of the Consuma, east of Florence, is far from trivial: any ascent with an altitude gain of more than 1,000 metres deserves respect. For many local cyclists, this is a place of suffering that resembles an hour-long FTP test. However, on our gravel bikes today, we will climb admiring the view, instead of a power meter screen. And stop for coffee, ice cream, sandwiches and anything else we want because these three days of cycling exploration are all about having fun and taking it easy.florence bike tours

The extraordinary thing about the Tuscan road network is how widespread it is. With the sheer number of roads and lanes, the combinations to get from one point to another are practically endless. The region’s famous strade bianche are mainly located south of Florence, but our route instead takes us on the climb to Pontassieve where olive trees dot the landscape, before being replaced by vineyards as we approach Castello di Nipozzano. Here, the Frescolbaldi family produces a Chianti appreciated all over the world. bike tours florenceAs we climb, the vegetation of the woods is more akin to that of Alpine mountains. The tallest trees provide a welcoming shade that keeps us cool as we pedal on. Every so often, we come across families having picnics in roadside clearings or an occasional hiker, but for most of the time, we are the masters of the road – well, road in name only, as we are far from the asphalt. bike tour from florence to sienaThe network of trails that crisscross this area is wide-ranging. The partisans of the Resistance took refuge in these woods during the Second World War and managed to escape from the occupying forces hunting them down. 

bike tour chiantiThis part of Tuscany offers a perfect alternative to the more famous routes of the Strade Bianche or the Chianti Classico. As we descend on smoother roads back to Florence, I think that Italy truly is a unique place for its variety of landscapes and offerings. In three days, starting and finishing in Florence, we enjoyed three completely different adventures.

At the end of the day, we have another appointment for an evening aperitif in a rather exclusive place – at the table in the rowing club of Florence, usually members’ only, with magnificent views of the Ponte Vecchio. 

bike tour florence in chiantiGigi, the club director, welcomes us warmly and their friendly members ask us questions about our trip. The bicycle is ideal for meeting other people, especially in this environment. Cycling and gastronomy certainly have much in common. This is why, in Italy, the two can never be separated: to understand one of those two cultures well, one must experience the other, too.  

Rolling Dreamers

Established by Matteo & Andrea, Rolling Dreamers’s founding desire was to share their passion for sport and travel. What started with a single adventure – cycling from Italy to Barcelona and competing in the Barcelona Triathlon – has evolved into a way to create unforgettable adventures to visitors from all over the world. In addition to training athletes for endurance sports, they offer tours, guided rides and gravel bike rental from their base in Florence. Whether riding the Via Francigena to Rome, exploring the wilderness of Abruzzo or guiding visitors around their local Chianti hills, Rolling Dreamers are committed to making sport a means of sharing positive values and respecting one another and the planet.

Find out more

florence bikes


Made for performance, 3T has evolved from manufacturing components to become a leading bicycle manufacturer. Founded in Turin in 1961 and now based in Bergamo, as the innovative brand turns sixty, it has launched the Exploro RaceMax frame. This versatile range comprises the Strada road frame and the Exploro and Exploro RaceMax off-road models, the latter available in a Boost e-bike version.

Find out more

florence bike ride


Pissei began life in the Tuscan city of Pistoia in 1978 under the name Ellegi. From the off, they specialised in sportswear, adopting their distinctive current name in 2006. 

As passionate cyclists, they are in tune with their customers’ every need.florence gravelPissei stands out for their 100 per cent Made in Italy garments, which ensures top-of-the-range handmade excellence and quality control. Developing their range by working closely with experts, they mix functionality with an inimitable style, offering clothing for every cyclist on any terrain.

Find out more

Shop now