From Tuscany’s famous strade bianche, to the wide open vistas of the Val D’Orcia, the rural and undiscovered landscape of Northern Lazio and finally to the magnificent Eternal City of Rome.

Day 1

Florence to Siena: 95 km, 2100 m

Central Florence is a maze of one-way streets; it is a wonder anyone can get anywhere. We wind our way through them directed by Komoot and a helping of local knowledge from Matteo and Andrea of the Rolling Dreamers; our guides for this four day trip. When we cross the river Arno, one of the classic views of the city reveals itself: the Ponte Vecchio connecting the two halves of the city. That will be our route out and on towards Rome. But not yet. First, we have breakfast waiting.

The Portrait Hotel Firenze has provided a breakfast spread that is so abundant one suspects they know about the calorie burn we have ahead of us. In fact, the manager Diego is himself a cyclist and joins us to ask about the route, the bikes, the kit. As he sees the bikes lined up against the wall, there is a twinkle in his eye and he promises that next time he will join us. This hotel will be the first bookend of the trip with the Portrait Roma, its sister hotel forming our final stop in Rome.

Having had our cappuccino or espresso (and in some cases both – you know who you are) we roll across the Ponte Vecchio, departing through the Porta Romana or Roman Gate – the most spectacular and grand of the city gates; built in such a way that travellers in the past dong the opposite journey to ours would be impressed arriving in Florence even after experiencing the magnificence of Rome.

The first climb is mercifully on road, allowing for a warm up before we hit the first part of gravel. Almost immediately after leaving the city, the vineyards begin. The regimented lines of plants will be our backdrop for the entire day as we go through three of the Chianti regions: the Florentine hills (colli Fiorentini), then Chianti Classico and finally, the hills of Siena (colli Senesi). It’s always a good idea to ask for the local Chianti. Asking for a Chianti from Florence when in the hills of Siena might get you a stern look. Or worse.

Considering rainfall is their only source of water, the vineyards are surprisingly green. The silvery ever-green of the olive groves accompanies it and classic Tuscan views are to be had in all directions. The first gravel segment arrives and there is something special about riding the Strade Bianche of Tuscany on a gravel bike. Many locals consider Tuscany to be the spiritual home of gravel or mixed-surface riding. The season here begins (under normal circumstances) with the Strade Bianche race and Gran Fondo and ends with the Eroica and Nova Eroica, all of which are held on a mix of road and gravel. Our total kilometres will be slightly weighted, 55% in favour of gravel. Or at least that’s the plan.

If you have ever seen a photo of Tuscany, you can imagine the terrain: hilly, yes but nothing approaching the ferocious climbs of the more mountainous north. Even the bikes in 1x build have all the gears needed for the route. All of today’s roads are shared with vehicles but we see very few as the rural roads lead towards Volpaia for lunch. 

Italian life revolves around mealtimes which can be quite strict in when they start and finish but fortunately the people of Volpaia are not such sticklers and we order “pasta al pomodoro” – pasta with a simple tomato sauce – for everyone. It’s hard to think of a national cuisine that better matches the nutritional requirements for cycling.

We cannot get too comfortable, more KMs are to be done. There are tiny hamlets, individual dwellings and lazing Pastore Maremanni – Tuscan sheepdogs – that stare at us indifferently as we ride past. As we approach Siena the landscape begins to change. It is almost imperceptible from one minute to the next and yet by the time we begin to approach Siena as the light is failing, the hills are changed from those of this morning: they are wider, more open and more expansive. The workers are out harvesting the grapes as we descend down through the vineyards of Castello di Brolio. 

In the last of the daylight we arrive at the hotel just in time for dinner. The hotel itself is a typical Tuscan agriturismo and is the perfect stop off for this tour. At dinner there is no menu, so no decisions to make, just fine local seasonal food, allowing for any particular dietary requirements of course.

Next, Day 2: Siena to Proceno

If you would like to experience cycling from Florence to Rome, we have options for Self Guided Tours or our fully supported Pro Tour