How to tackle the most beautiful cycling route in Italy

Adam Ruck
The Val d’Orcia, recognised by Unesco - This content is subject to copyright.

A target gives purpose to a bike ride, and the news that the pilgrimage route to Rome has been resurrected as a cycling trail is an invitation to saddle up. Completed in 2016 after a 10-year campaign of marking and mapping, the Via Francigena is the longest signposted cycle route in Italy: 620 miles from the Great St Bernard Pass to St Peter’s. Independent cyclists can download the maps and look out for the blue and white flashes by the wayside. 

For an easier and more sociable holiday, I joined a guided group organised by the cycling tour operator Saddle Skedaddle, which has added the last 200 miles of the Via Francigena to its programme: a “leisure cycling” ride through the olive groves and vine-clad hills of fashionable Tuscany and less-so Lazio, graded three on Skedaddle’s five-point scale of difficulty. 

The route is more than 1,000 years old, first charted in 990 by Archbishop Sigeric, who travelled to Rome to receive his cloak of office and kept a diary of the 79-stage return journey to Canterbury. Our trip follows Sigeric’s first 19 stages in reverse, starting from the walled town of San Gimignano; or, to be exact, from Fattorie Santo Pietro, a vineyard agriturismo estate below San Gimignano, reached by a long, steep and bumpy dirt track. 

“You’ll be riding back up this in the morning,” says our head guide Christina, as we bounce down in the minibus after a two-hour break for sightseeing and strolling. The tour proper starts, as is only fitting, with a feast. Chianti and reminiscences flow, and first-time Skedaddlers are welcomed into the fold. Almost half a century separates the extremes of our group, from millennial to a sporty septuagenarian with a preference for dirt over boring old Tarmac. A hi-tech cyclist has brought his own bike and a handlebar computer to record every possible statistic of our ride. A newcomer to distance cycling has reserved an e-bike – “because it’s a holiday, isn’t it?” 

Expect dirty roads and cheeky climbs Credit: PETER ADAMS

Halfway through the panna cotta, Christina bangs her glass with a fork. “Welcome to Tuscany – lots of dirty roads and cheeky climbs! We will ride through many beautiful old towns and they were all built on hilltops. But this is leisure cycling, so we don’t start until nine.” 

After breakfast, support guide Stefano unfolds a map on the ground and outlines the day, in a mellifluous tenor that makes our itinerary sound like a recitative by Pavarotti. “We don’t touch Poggibonsi, and we don’t touch Pienza. Follow the old railway track to Colle di Val d’Elsa, and please dismount in Siena. This is important. Siena is very touchy about this.”

No cycling in Siena Credit: SABINO PARENTE

Some of us dismount moments after leaving the Fattorie, losing traction on the first slippery hairpin.

Beneath a cloudless sky, Tuscany is a picture: the fields not yet cut and dried, but spring green and ablaze with poppies. Cypresses line the road and prick the skyline in a landscape lifted from a Renaissance painting, but offer no meaningful shade. A stretch of road with a canopy of umbrella pines makes a change, but their roots corrugate the road surface. Could we have the cypresses back, please? 

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Every cycling group needs an e-biker, to be the butt of its taunts. “Cheat!” and “How much for a tow?” we cry, as Helen flicks a switch and sails past, quoting her favourite lines from A Room with a View as the rest of us toil up the hill wiping sweat and sun cream from our eyes.  

Pilgrims of old took the high road over the hills to avoid malaria, says Stefano. Much as we complain about the cheeky climbs – and tougher ones, termed “interesting” – the downhill “dirty road” bits are the most trouble. 

“Lean back, don’t grip the handlebar too tight and let the bike find its own way,” says Christina, standing on the pedals with her bottom over the back wheel. Braking with a loose grip takes some doing. After a few grazed knees, some of us swallow our pride and walk down the most awkward sections. 

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During pauses we take turns on the e-bike, engage its Turbo setting and feel the surge of power as we press the pedal. All right! But would the downhill rush be so rewarding, if we hadn’t done the uphill grind? Would the beer and ice creams taste so good? So long as we can make it up the hills Christina puts in front of us, we would rather not be seduced by the e-bike. If someone is seriously off the pace, the guides must find another solution. There are enough of them to split the group and find an alternative route involving fewer hills and less gravel.

Thirty miles may not seem much for a day’s cycling, but progress on the country paths is slow, and towns like San Gimignano keep popping up as an excuse to stop for pictures.  

San Gimignano Credit: GETTY

Tuscany is full of treasures, and our arrival at Siena is much anticipated. Having pushed our bikes on to the world’s most beautiful non-square, the shell-shaped Piazza del Campo, we line up for group photos in front of the Palazzo Pubblico. Now what? Its door is open and we have a window of leisure time before supper. The stripy Duomo with its dazzling mosaics is a few minutes’ walk away.

The group decision is to enjoy the scene with beer in the foreground: cycling is thirsty work. After a second round it’s time to find the hotel and reassemble for supper after a quick shower. We will saddle up again after breakfast, so that’s Siena done and dusted. A pretty square with a fountain and a gelateria is all the sightseeing that leisure cyclists require.

After Montalcino and its immaculate vineyards, Tuscany’s highest mountain, Monte Amiata, is the backdrop to our exertions for two days. Medieval pilgrims did not feel the need to go up it, thank goodness. 

Monte Amiata Credit: GETTY

A long, hot climb brings us to the highest point on our journey, the fortress village of Radicofani (2,470ft), which commands the lovely Val d’Orcia, recognised by Unesco for “the beauty of a well-managed Renaissance agricultural landscape”: paradigm Tuscany. Its agriturismo is a highlight, too; outstanding food, a charming menagerie and a pool with a view. Crossing the regional border is an important moment of transition. “I love Lazio,” says Christina; “Tuscany is too perfect!”

“Lazio drivers are the worst in Italy,” says Stefano, a proud Tuscan. Olives give way to hazelnuts and the landscape takes on a more disordered look. Between villages on outcrops we ride down dark lanes enclosed by walls of volcanic rock.

The scene opens up when we crest a brow and look down on the shining mirror of Lake Bolsena, the largest of central Italy’s crater lakes. Christina calls a halt and offers us a choice: by road, downhill all the way to our lakeside hotel, and beer, in half an hour; or a scenic track – “more interesting” – through the fields to the old town of Bolsena and its fortress. Beer in half an hour gets the majority vote and the group splits. 

Lake Bolsena Credit: ©FPWing - stock.adobe.com

After a close encounter with a ditch on the scenic route, I’m glad of the chance to wash Lazio’s rich earth off my weary body in the lake.

The warm-up to our next adventure is a steady climb to Montefiascone, a fine belvedere 1,000ft above the lake. While we take in the pretty scene and refuel with energy bars and cherries, Christina’s phone rings. Her face darkens: Stefano, today’s driver, is in trouble with the carabinieri. “And he has the lunch. Disaster!”

Montefiascone Credit: ©e55evu - stock.adobe.com

The police will not allow picnics in the town park Christina has selected at the foot of Viterbo’s Centro Storico and papal palace. Finding another picnic spot is too complicated. Is the group prepared to ride another 12 miles to the hotel at Vetralla? It is, and finds lunch waiting in the garden, with wine included since our cycling is done for the day. An afternoon walking tour is on offer, but the bedroom calls. Calm descends, disturbed only by snoring and the cicadas’ whining descant. 

At Sutri we picnic more successfully beside an amphitheatre, some Etruscan tombs and a monolithic chapel decorated with a mural of pilgrims. Charlemagne came through Sutri on the way to his coronation in 800, possibly led by a less exacting guide than Christina, who makes us ford a stream (“Keep pedalling!”) and selects a track better suited to crampons than wheels for our approach to Campagnano. “You’ll look up and think: I’m not cycling up there. But you are!”

Sutri's Roman amphitheatre Credit: ©asferico - stock.adobe.com

Cycling and hiking versions of the Via Francigena share many off-road sections, and pilgrim sightings become more frequent as we get closer to our destination. We cyclists must be a great annoyance to those on foot, but they stand aside and bear it bravely, wishing us “Buona pedallata!” as we ride by. Our last 10 miles are an easy ride on an exercise trail beside the Tiber, busy with runners, cyclists and roller skaters… but no pilgrims.  

“They go over the hills and walk down to the Vatican,” says Christina. “It’s a beautiful approach, very emotional. Mountain bikers can do it too, but it needs skill and there is a lot of traffic” – not suitable for us. 

Our peloton keeps its shape through the city centre traffic lights and tramlines before rounding the Castel Sant’Angelo to cut – politely – through a throng of tourists and costumed gladiators. The Via della Conciliazone is our finishing straight, then it’s sweaty hugs and handshakes all round and group pictures in front of St Peter’s. We may not be bona fide pilgrims, but there is a great sense of completion. 

Journey's end: Castel Sant’Angelo Credit: GETTY

I take my Credenziale log book to the pilgrimage office for a final stamp and a scroll to take home. “We have cycled 227.56 miles, climbed 5,732 metres and burnt 13,351 calories,” our scorer says. Now what? It must be time for a beer. 

How to do it

The Via Francigena leisure cycling holiday is a nine-day guided tour from Pisa to Rome, graded moderate, with seven days’ cycling, available through Saddle Skedaddle (0191 265 1110; skedaddle.co.uk). It costs from £1,440, not including flights, evening meals or bike hire (£160; £180 for an e-bike). Departures in May, June and August 2018. Skedaddle also offers a mountain bike version of the trip, on more challenging off-road terrain, and can supply the pilgrimage Credenziale on request.

For more information about the pilgrimage, see pilgrimstorome.org.uk; and for detailed maps of the Italian stages of the route, see viefrancigene.org