Florence to Rome – Riding the Pilgrims’ way

Foto di Rolling Dreamers | Testo di Emilio Previtali | Tempo di lettura 12'

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 D+

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. 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 region. 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. 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.

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 as soon as we arrive 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.

In the last of the daylight we arrive at Ca’Bianca where Simone who runs the hotel will also be making us dinner. There is no menu, so no decisions to make, just fine local seasonal food, allowing for any particular dietary requirements of course.

Day 2

Siena to Proceno: 119 km – 2550 m D+

After a superb breakfast (again prepared by Simone) we are immediately onto narrow gravel roads lined with Cypress tress. It is today that we will join the Via Francigena and from here on, we follow it as closely as possible all the way to Rome.

The views stretch even further than yesterday. This is classic Tuscany. It is here that the most famous photos and films of the region have been taken or shot. The road surface is pretty good though heavy rain can make the gravel roads perilous for the inattentive, the water carving deep lines across them.

We ride on, past Buonconvento the home of Nova Eroica, through more vineyards that skirt the hill top town of Montalcino, stopping at some of the many water fountains that line the route. We pass walkers, some who greet us, others whose headphones block the sound of our approach. Everyone here is on their own personal journey; that is one of the things that makes the Via Francigena so special: everyone rides or walks the same path but they all have unique thoughts, experiences and reflections at the end.

After climbing another hill, we see San Quirico D’Orcia in the distance and that means lunch is near. Before we can eat, there will be the short and steep climb into the town itself. Once that is done, we ride through the narrow streets that seem unchanged by the passing of time.

Today is a long day and there is only time for a panino (prosciutto and pecorino, that seems to be the locals’ choice) before we continue to Vignoni Alto – a fine and typical example of a borgo or semi-fortified village. The south gate opens to an immense panorama of the valley below.

Shortly after a brief stretch on the asphalt road to Rome, the Via Cassia, we enter into Lazio. There is no signage announcing the change of region although it is now dark and our focus is on the more concentrated small, area of gravel road in front of us. When we do finally arrive in Proceno, we are warmly greeted by the Contessa whose family inhabit the castle and also run the Albergo Diffuso that will be our home for the night as well as providing our dinner.