It was my first day of walking the Via Francigena trail along with a group of ten people. We were a diverse group, comprising of people from different countries and different age groups.

It was a bright October morning, and we were standing on a panoramic point overlooking the Arno Valley draped in a series of small hills, with cypress and olive trees in the heart of Tuscany. “San Miniato, where you are standing right now, has been on the crossroad since the middle ages. Due to its strategic location, it was a bone of contention between Florence and Pisa. As it lies roughly twenty-miles away from each of them, it earned a name of the ‘twenty-miles town’,” explained Erica Masani, my environmental guide.

Almost forgotten for centuries, the Via Francigena is undergoing a renaissance. In 2009, the Italian government decided to revive the Italian leg of the route based on the journal written by Sigeric, archbishop of Canterbury, on his way back from Rome in 990 AD. However, the revival was a bumpy ride. Roadblocks existed both in the landscape and mindscape. Over the past few years, a sensible modern route has been waymarked through Tuscany to avoid stretches of main road and hiking maps have been published. From a time when locals didn’t want the pilgrims in their area to offering them free food, water and shelter, Via Francigena has come a long way in less than a decade.

Erica spoke encyclopaedically just about everything we could ever want to know about Via Francigena, from the historic relevance of the walk to the power struggles of the middle ages to the fact that every rural home has thousands of olive trees.

She said, “Via Francigena is to Italy what El Camino is to Spain. In the Middle Ages, the 1,200-km pilgrimage path began from the Canterbury Cathedral in England passing through France and Switzerland before reaching the eternal city, Rome.”

Highlighting the route’s rich history and long pilgrimage tradition she continued, “The route welcomed travellers from the Etruscan merchants, Roman soldiers, pilgrims to Europe’s greatest minds. As a result, it had seen a succession of civilisations, architecture, culture, and gastronomy.”

The journey

The whole trail of 1,200-km takes approximately 90-days but I decided to do a portion of it (almost 100-km) in five days. Those five days were an excellent introduction to the Tuscan countryside — unspoilt landscapes, UNESCO protected medieval towns, delightfully open-hearted people and exceptional gastronomic delights. And, to top it all, it was a more sustainable way to explore Tuscany when mainstream holiday destinations are struggling with over tourism.

We continued to be guided by simulacrums of the ancient pilgrims, a tiny image of a pilgrim appeared almost on every patch of the trek – whether, on a lamp post, small signage or spray painted on the pavement – to guide modern pilgrims like us.

Day 1: San Miniato to Gambassi Terme (24km)

Our first day was long but scenic, where the classic Tuscan vistas welcomed us with quilted green hillocks, skirting vineyards, freshly harvested wheat fields and olive groves. After three hours of walking on a snaky path in some 28˚C, we reached the cool surroundings of a recently restored 1,100-year-old Romanesque Church — Pieve a Chianni. It was here, where Archbishop Sigeric stopped on his way from Rome to Canterbury. After a hearty Italian picnic lunch, we continued our journey to the vertiginous town of Gambassi Terme.

Vineyards, Via Francigena, Tuscany

Day 2: Gambassi to San Gimignano (17.6km)

The second day was one of the most anticipated days of our walk as we marched towards San Gimignano, a UNESCO world heritage town dubbed as the ‘Medieval Manhattan’. Though the route was shorter than the earlier day, it was more diverse in appeal – freshly overturned fields with earthy fragrance, never-ending golden-yellowish vineyards where most grapes were harvested, dry sunflower fields, long avenues of cypresses, rolling hills crowned with vertigo-defying citadels and lush forests that had started adorning fall colours.

San Gimignano, the UNESCO world heritage town

At mid-afternoon, we reached the city of towers and straight away we began our guided tour. Standing on top of the tallest tower – the Torre Grossa – we heard tales about the patrician families who built around 72 tower-houses as symbols of their wealth and power.

When the Tuscan sun blanketed the whole valley into its golden glow, an expert sommelier took us on a sensual journey of wine-tasting at the Museo del vino Vernaccia di San Gimignano. We tried several varieties of Vernaccia, a fruity local dry white wine produced only in Tuscany since the 13th century before wrapping our day with a wonderful homemade Tuscan meal.

Vernaccia Wine tasting in San Gimignano

Day 3: San Gimignano to Abbadia Isola (25.4km)

With a reluctant heart, I left San Gimignano to cross the Elsa river valley where we jumped into the freshwater stream and rested for a while before reaching Abbadia Isola, a 1,000-year-old abbey. This large Romanesque abbey was covered with marshlands until the 11th century when Benedictine monks took charge and built a church and a monastery.

Abbadia Isola, a 1,000-year-old abbey

Day 4: Abbadia a Isola to Siena (18.6km)

A golden misty morning greeted us as we made our way to the perfectly preserved medieval walled town of Monteriggioni. Despite power changing hands several times, the Lego-sized town didn’t lose a bit of its Medieval character.

“The castle of Monteriggioni has never been conquered. And, that’s why nothing has changed here — from cobbled streets to its city walls.” said the Mayor of the town while we stood on the fortified walls of the castle overlooking the valley.

The fortified castle of Monteriggioni

Picturing ourselves as medieval warriors, we had fun trying armour suits and medieval swords at the Armoury Museum. When in Italy, it’s a cardinal sin to not treat oneself with gelatos. And, I did exactly what the Romans would do in Rome.

Staying on course with time, we made two quick stopovers before reaching Siena. The medieval masterpiece of Tuscany was an important stop for pilgrims, artists and traders, where architecture, art and spirituality cohabited in perfect harmony. I was particularly excited to see Duomo – Siena’s black and white striped cathedral, and Piazza del Campo — world renowned for ‘Palio’ (a historic horse race).

Piazza del Campo, Siena

Day 5: From Lucignano to Buonconvento (13.6km)

The final stop on this section was dedicated to gastronomy and why not, after all, we were in Italy. The Tuscan countryside is like the Chianti produced there – meant to be savoured rather than gulped. A short ride from south of Sienna brought us to Lucignano, from where we walked on the soft ochre coloured Sienese clay hills topped with a line of cypresses to reach Buonconvento. Food in Italy tastes much better than anywhere else. It’s been several months since I returned from the trip yet my mouth starts watering when I think about Cacio E Pepe, and Fagioli (white beans) I had at Fattoria Pieve a Salti, a 700-hectare Agritourism organic farm near Buonconvento.

Fattoria Pieve a Salti near Buonconvento

The trip had a befitting finale with wine tasting at Italy's first all-woman run vineyard — Donatella Cinelli Colombini where I was introduced to a novel concept of wine tasting with music.


As we walked, we recreated the 10th-century experience — swapping diesel engines for strong legs, pencil heels for hiking boots, and technology gadgets for adventure gear. We wanted to emulate the ancient pilgrims as much as possible, however, one important thing that differentiated us, the modern pilgrims, from the ancient pilgrims, was our motivation – while they were driven by religious spirit, we were stoked by adventure and slow travel.

I might not be a classic pilgrim but you don’t even have to be religious to experience the joy of walking the 1,200-years old lost pilgrim path to Rome. I met and bonded with people who I could have never crossed paths with in ordinary life — who don’t just do lip service about bringing a change in the world — they actually walk the talk.
This trail is no ordinary trail, it connects you with the heart of Tuscany, and in doing so, offers enlightening insights into the simple pleasures of Tuscan life and provides a mirror to gaze and reflect on your own.


How to get there?

Fly from any Indian metro city to Florence or Pisa and then take public transport to reach San Miniato.

When is the best time?

May-June and September.

Where to stay?

You can stay at pilgrim hostels, monasteries or 3-star hotels on the trail. I stayed at La Cisterna in San Gimignano, Pilgrim Hostel Sigerico in Gambassi, Ostello Contessa Ava in Abida Isola and Hotel Italia in Siena.

How to do it?

A self-guided tour for three days starts at €140pps and guided group tour for five days start at €570pps with Sloways. Prices exclude flights.

What to pack?

Correctly fitting hiking shoes, comfortable clothing and a hat are vital. Keep your daypack light with a reusable water bottle, snacks, sunscreen and camera.

For more information on the Via Francigena see or

Archana Singh is a brand strategist turned travel entrepreneur and writer, who likes to visit offbeat places in search of untold stories. Follow her on Instagram.

— All images courtesy of the author.