In case you missed it, you can start with Day 1 – Florence to Siena

Day 2

Siena to Proceno: 119km, 2550m

After another superb breakfast we are immediately onto narrow gravel roads lined with Cypress trees. 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. Houses appear on hilltops looking like magazine covers, their driveways winding invitingly along the ridge. 

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. The only real heavy going is an impromptu trip across a muddy field to make coffee on the portable stove proper bike packing style. It doesn’t matter what you need, one of our guides seems to have it: coffe machine, check. Spare gel, check. Battery bank for the phone, check. Tubes, tyre sealant, tools… its a wonder they can pedal the bikes with it all.

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. 

The Via Francigena often splits into two: the mixed path for walkers and cyclists and the route for cars. Sometimes we follow one, sometimes the other. Our guides have ridden this route many times and personally discovered when the mixed path is impassable on a bicycle. On those occasions we follow the route for motor vehicles but we see few: some local farm traffic and a camper van or two.

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 houses were built clustered together for both the sake of safety and practicality. The south gate opens to an immense panorama of the valley below. Here the vineyards become less and less frequent, giving way to arable land. The palette of greens becomes yellow, gold and brown. 

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. 

During the heat of the day it was just jerseys and shorts but for the last part of the ride there are sleeves, gilets, jackets… it is raining and the lack of warmth from the sun makes it feel like an entirely different season. 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. Unlike traditional hotels an Albergo Diffuso has rooms or apartments dotted around a location. In this tiny village it is an ideal way to feel at home, as our group separates after dinner to their own quarters.

That dinner is, of course, another multi-course marvel: a cured meats and cheese starter, a first course of pasta and a second course of pork and potatoes. Everywhere we go there is a clear pride in the local food and a seemingly innate knowledge of what is in season. We retire warm and content.

Read next: Day 3 Proceno to Sutri

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