Hiking the Via Lauretana

Nick Kelly, accompanied by friend Brendan, entertainingly documents his 5 day walk from Siena to Cortona...

Owing to COVID travel restrictions, I’d been deprived of the chance to visit our family’s little corner of Tuscan heaven at the foot of the hill of Cortona for nearly two years. I’d also long been envious of those energetic Camino-goers who Instagram their way across swathes of Northern Spain. When I finally found a 7-night window in October when I could escape Ireland, I decided to see whether I could cram both experiences into one.
To my delight, I turned up what seemed like the ideal solution on the Tuscan Tourist Board website: a section of the Via Lauretana, an ancient pilgrimage route, wending from Siena to Cortona over 5 days and 130 kilometres. (The Via Lauretana historically led right across Italy, from Rome through Tuscany and Umbria to the shrine of Loreto by Marche’s Adriatic coast, where the original walls of the Virgin Mary’s house were said to have been transported by retreating Crusaders in the 13th Century)
Having persuaded my friend and former adland account manager Brendan to book the flights, I then realized that while the route may be ancient, its promotion as a viable tourist excursion is very recent – so much so, in fact, that I couldn’t find anybody to arrange the trip for us. As I observed to Brendan, while we’d often idly discussed setting up an agency together we hadn’t realized it would be a travel agency.
I spent many days studying the not-very-detailed online maps, endless surfing for the best options from a surprisingly limited range of hotels along the route, then negotiating with each hotelier individually (via a creaky translation App) to arrange transport of our bags onwards to the next night’s accommodation while we walked. After a few false starts, I finally had a plan of action that looked like it would work. And, for the most part, it did…
Day 1: Rome – Siena – Vescona
While both Pisa and Bologna are closer and easier airports to negotiate, our limited schedule meant that we needed to start walking on our day of arrival, so we elected to take the earliest flight available from Dublin. This landed us in Rome’s Ciampino airport at 10.40 am where our most efficient and pleasant Transfeero driver awaited. Our three-hour (and €400) road trip took us directly past our first booked hotel, the Castello Di Leonina, where we dropped our bags before continuing to Siena’s Porta Dei Pispini which marked the start of our hike.
Having wolfed down some sandwiches and filled our water bottles in a café very conveniently located just outside the city’s picturesque gate, we set off on our hike towards Vescona. The initial few kilometres took us through the suburbs of Siena and along some fairly busy narrow roads, always following the discreet but plentiful red and white waymarks (they come in both new sticker and more traditional paint daub form, with the occasional fancy “Via Lauretana”-branded arrow sign giving distances to the next destination). An early warning of the limitations of this system came as the signs disappeared around some recent roadworks at Arbia, possibly displaced along with their host lamp posts, causing us to miss a turn. Using a combination of SatNav, the very inadequate large-scale map provided in the only (Italian-language) guidebook available for the Via Lauretana, and the slightly more detailed Insight Guide pull-out map for Tuscany, we managed to rejoin the route a kilometre up the road. This was the first of a regular series of moments of uncertainty on our journey over the coming days. One of the fanatastic but also complicating aspects of the Via Lauretana is that it is, as yet, largely undiscovered by the hiking community. On our entire camino we only came across one young couple coming the opposite way. If you’re after tranquility – and a certain amount of chaotic meandering – you’ve definitely chosen the right path.
We finally left the tarmac of the Provincial SP438 and had our first taste proper of the region’s most unexpected natural phenomenon, the “almost lunar” (as one guidebook aptly describes it) desert landscape of the Crete Senesi, a wide plateau of picturesque but arid clay hills.  As our brand new hiking boots quickly whitened with the fine dust, we could quite easily imagine ourselves in a Spaghetti Western or on the surface of Mars.
Within a relatively short time we arrived at the Castello Di Leonina for the second time that day, this time on foot, allowing us to appreciate its magnificent location surmounting a hill, its approach avenue shaded by a stately colonnade of pines. This four-star hotel was much the poshest one I’d booked for our trip, but the remoteness of this first stretch presented no other obvious options. We were a few kilometres short of Vescona itself, the first official waypoint – but as we would confirm the next day, this is no more than a tiny cluster of mostly deserted houses, with not even a shop or café, much less hotel accommodation, to offer.
We concluded what had been a long day’s travel, though a relatively short walk, with a welcome shower. Sadly the fact that the hotel’s highly-rated restaurant was closed to host a wedding meant that we had to make do with sandwiches and red wine in our room.
Total distance: 14km
Total walking time: 3 hours
Accommodation: Castello Di Leonina, Strada Leonina, 5, 53041 Asciano.
Day 2: Vescona – Serre Di Rapolano
Unbroken blue skies over the fresh snap of a Tuscan Autumn morning greeted us as we strode down the far side of the hill of Castello Di Leonina. Within a couple of kilometres we arrived at the much-heralded “Transitory Site”, a striking minimalist modern sculpture on a rise that offers magnificent 360 degree views across the Sienese plains.
As our route continued along the dusty path across increasingly undulating bare clay hills and through deserted hamlets completely devoid of food, water, toilet facilities or, indeed, humans, we started to appreciate how inadvertently perfect our timing had been. Even in the low 20s Celsius, we were soon stripped to t-shirts and hoovering through our bottled water supplies. Had we tried this hike in the much hotter mid-summer, we’d have run out of steam and hydration very quickly. And if there’d been any kind of rainfall at all, the heavy clay underfoot would have turned this landscape into a Somme-like quagmire.
With very few vertical structures to attach a sticker to, and our route taking us across farmland where no historic right of way was going to be allowed to interfere with the primary seasonal work of ploughing, we found ourselves hopelessly lost and disorientated. At one point we hiked all the way up to the top of a steep clay hill – passing a pack of yappy but luckily not aggressive farms dogs and stepping gingerly around an adder lying across the middle of the path – only to realise that we’d taken a completely wrong turn and had to retrace our steps.
We finally triangulated our various inadequate maps and App-translated route notes and struck out in the right direction. The rigours of a fairly steep and, by this time of day, warm climb were offset by the stunning vistas back towards the now barely-visible steeples of Siena across the otherwise empty hillscape, and in my case by the extendable hiking poles which I’d felt rather foolish packing but now was greatly appreciating. We finally hit a high and winding paved road, so quiet that no vehicle of any kind passed us over the surprisingly lengthy stretch into Asciano. Another feature of our walk was how often we underestimated the distances and / or our ability to burn up time in wrong turns. With our water bottles now empty and having only had a couple of half-melted energy bars for sustenance since breakfast, we walked into the ancient walled town well after lunchtime with grim foreboding. However, to our great relief and delight, it turned out that several refreshment options were still open in the Piazza Garabaldi to cater for laggard tourists like ourselves. We recharged our batteries on delicious pizza, strong coffee and ice cream, and refilled our bottles.
The final 6.5 km stretch from Asciano to the pretty hilltop village of Serre Di Rapolano was across relatively flat and verdant fields, a welcome respite after our earlier haul through the clay dunes of the Crete Senesi. By the time we reached Serre di Rapolano both the sun and our energy levels were fading fast, and the long soak in the hot spring baths of nearby Terme Rapolano I’d envisaged for the end of our second day’s hiking was clearly too ambitious.
Our accommodation for the night, at the Antica Granaione tucked away in an exquisite little piazza towards the top of the town, was a delight – an ancient townhouse upgraded in flamboyant style and with all modern comforts, presided over by a charming and vivacious Cuban manageress. There was even a rec room with a well-tuned piano, whose ivories were tinkled briefly before we showered off the day’s extravagant dust. After savouring the views from our lofty window over the terracotta rooftops to the darkening Tuscan plains beyond, we wandered back down through the empty streets to the restaurant our hostess recommended (there didn’t seem to be many other eating options on a Sunday night).
There was even a rec room with a well-tuned piano
San Rocco was located in the rear of a tobacconists and entirely deserted when we arrived, which was not promising. But the pasta Alfredo was excellent and as we gradually filled up, so did the room.
Total distance (including detours and wrong turns): 30 km
Total walking time: 6:19
Accommodation: Antico Granaione, Via F.lli Rosselli sn, Serre di Rapolano Toscana 53040. (+39) 0577 236016 / www.anticogranaione.com / reservation@anticogranaione.com
Day 3: Serre Di Rapolano – Sinalunga
After a great night’s sleep, a good breakfast and an effusive farewell from our hostess, we struck out on the next leg of our journey. An hour and a series of comically wrong turns later we realized that we were inadvertently retracing our steps back towards Vescona. Once we finally embarked on the right path, we quite quickly found ourselves on the San Gimignanello estate, our route taking us between forest and vineyards up to the handsome castle itself, which, while well-maintained and clearly occupied, showed no signs of the coffee or lunch which our guidebook had promised might be available.
The red and white marker let's you know you're headed in the right direction...
We gamely continued along the path before getting ourselves comprehensively lost in the increasingly overgrown thickets surrounding a deserted farmhouse where the few waymarkers we found only added to our mounting paranoia that some hiker-hating local had deliberately sabotaged our route. Again, by triangulating guidebook, map and compass we eventually managed to find our way to a quiet paved road where – cheering and air-punching – we picked up a precious red and white marker again.
The route brought us along the shoulder of the spectacularly located Scrofiano, another sleepy hilltop hamlet. Through the pass we caught our first glimpse of Cortona in the far distance. Once again, as we hauled up the steep alleyway into the village, we realised that whatever limited eating options were likely to be available were also likely to be closed, as a combination of our initial false start and our floundering lost in the brambles along the way had delayed our arrival until nearly 3.00pm, long after Italian lunchtime. The only small sandwich bar we could see had indeed stopped serving, but the proprietress, taking pity on us, filled our water bottles and sold us a couple of panini.
Thus fortified, we set off back down the hill, though not before getting thoroughly befuddled by more confusing waymarks on the path out of town. Finally by a process of elimination we found ourselves on the winding forest path that in turn issued onto the backroad that led us into the suburbs and then the centre of Sinalunga.
Stopping for a much-needed ice cream at the Bar l’Angolo Bossi on Piazza Garabaldi (every town has one, I’ve realized), I studied our itinerary and realized that the accommodation I’d booked for that night was another couple of kilometres further along, down a very steep hill. We descended to Il Rifugio di Dante, which turned out to be located, literally and figuratively, on the other side of the railway tracks in a not especially charming commercial zone of this not especially charming large town. But despite initial appearances, the rooms were very comfortable and the initially rather gruff manager earned our undying gratitude by squashing us into the back of her tiny car and driving us back up that formidable hill to the town centre where we dined deliciously at the excellent Ristorante Alle Volta.
At least, we said as we eventually rolled back down to our beds, we’ve already done the first stretch of tomorrow’s hike…
Total distance (including detours and wrong turns): 28 km
Total walking time: 6:30
Accommodation: Il Rifugio di Dante, Via Piave 35, 53048 Sinalunga. (+39) 0351
213 4287.
Day 4: Sinalunga – Valiano
Waking to a crisp and bright morning, we started off very pleased with ourselves, already, we reckoned, 2km down the road. Fairly soon our route took us into the Fratta Estate, strolling along straight ancient paths through wide vineyards and well-tended fields, intersected by small waterways, and the occasional handsome old building. We were thrilled to catch sight of a small herd of deer bounding across the plain.
Fratta Estate
As the morning ripened into a warm and cloudless Autumn day, the much flatter and more open terrain and generally easy-to-follow waymarking meant that we reached the impressive and well-maintained ancient fortress town of Torrita Di Siena for once in good time for lunch. We found a small bar directly opposite the picturesque town hall that served us panini and filled our water bottles.
Our afternoon took us through endless sprawling vineyards – we were now in the hinterland of Montepulciano – and, slightly more unexpectedly, some well-tended fields of cannabis which we learned later is grown, these days completely legally, for medicinal use.
Fields of medicinal cannabis
Throughout our journey we passed very little in the way of tourist infrastructure outside of the few larger towns – both a blessing, in that you have the route mostly to yourself, but also a curse when you’re in urgent need of food, water or toilet facilities. As the afternoon wore on, it became apparent that we would soon – very soon – require some of the latter. We entered the town of Abbadia with some relief, presuming that its long main street would boast a hotel, restaurant or at least coffee shop that would be able to provide what we needed. In the end, we were reduced to the extreme embarrassment of explaining our predicament to the tour guide at the local Villa S. Anna winery who took pity on us and allowed us access to their (extremely plush) restroom. Feeling in every way lighter, we pressed on for Valiano, on a long straight path across tilled fields which brought us under the thundering traffic of Italy’s main North-South motorway, the A1. Valiano was clearly visible on the horizon, but at a considerably greater distance than we’d initially calculated. At one point, rather ominously, our path flanked a fiercely burning ditch for several hundred yards – probably some kind of weed-clearing operation, but it felt like a Biblical portent.
Finally, as the afternoon waned, we approached the edge of the town and I decided we were close enough to tap our pre-booked lodgings into my Google maps. The thunderbolt that we actually had another 7 km to walk was intensified by my own belated realization that I had once previously undertaken Valiano’s testing incline some years earlier, on a bicycle training ride which was still etched painfully in my memory. Eventually I summoned up the courage to break the news to Brendan, who unfortunately was now suffering with a foot-blister the size of a ping pong ball. As we trudged up the steep approach and along the almost deserted main street of Valiano, both sun and conversation levels dropped. On the long descent into the next valley and climb up the hill beyond on an undulating country road, with no obvious restaurants or other signs of commerce in sight, our minds were fast turning to the question of whether there’d any kind of food available in the Agriturismo La Terra. Consumed with guilt at my poor route-planning, I swore to the stoically-hobbling Brendan that I’d pay the price of a taxi to the nearest open restaurant and back if necessary.
Luckily as we finally hauled our weary bodies up the driveway of La Terra, it became clear that we wouldn’t starve after all. As well as maintaining a small number of pristine and spacious self-contained bedrooms, the urbane owners offer all guests a home-cooked four-course dinner in a purpose-built outhouse with a wooden verandah giving wonderful views across the valley to Montepulciano. We slumped into garden chairs for a most welcome pre-dinner glass of white wine as we watched the last rays of the setting sun, and by the time our truly delicious meal had been scoffed, our spirits had recovered sufficiently for us to lead the three other couples present in a multi-national sing-song into the small hours, borrowing the guitar which our hosts had thoughtfully hung on the wall for such purposes.
With a borrowed guitar we lead the three other couples present in a multi-national sing-song into the small hours...
Total distance (including detours and wrong turns): 34 km
Total walking time: 7:26
Accommodation: Agriturismo La Terra, Via di Petrignano 2, 23045 Valiano di Montepulciano (SI). (+39) 0578 1998000 / info@agriturismolaterra.it / www.agriturismolaterra.it
Day 5: Valiano – Cortona
Well-rested and just a little hungover, we picked up the Via Lauretana again in the village of Petrignano, just a few hundred metres from La Terra. Our route took us off the minor road onto a pathway through farmland interspersed with commercial forestry. With Cortona visible on the now not-so-distant mountainside, our complacency led us astray yet again as we somehow wandered off track and found ourselves in a vast plowed field surrounded by thick trees with no visible waymarkers and no obvious path out. Rather than retrace our steps several kilometres, we struggled through dense overgrowth to follow a stream which we hoped would lead us back to relative civilisation. We were rewarded when we emerged beside a tiny chapel in a clearing and picked up the red and white stickers once more.
Out of the woods, we were now walking across the wide plain of the Valdichiana over freshly ploughed sunflower fields and vineyards towards our destination. Despite some random gaps in the waymarking, we found an underpass beneath the main Rome-Florence trainline and emerged up into the village of Ossaia. Our last stretch took us through the  winding lanes of the hamlet of Metalliano to the outskirts of Pergo, before we turned left and arrived at the familiar weathered walls of the restored fattoria that houses my family’s own apartment, noting that the signpost between its gates and the tiny and ancient adjacent church that gives Sant’Angelo its name and World Heritage Site status now boasts its very own Via Lauretana waymark, making Il Chiostro the perfect end destination for pilgrims (especially those who can’t quite face the last couple of kilometres climb up the back hill into Cortona and elect to postpone that pleasure until the next day).
Total distance (including detours and wrong turns): 22km
Total walking time: 4:21
Accommodation: Il Chiostro di Sant'Angelo, 52044 Cortona (AR). (+39) 0340 8601919 / robertomarri@yahoo.it
What we learned.
The recent promotion of Via Lauretana as a mini-Camino across Tuscany from Siena to Cortona does offer a fabulous new way to experience this beautiful and richly historic area.  It also opens a potential income stream for Cortona-based property owners out of season, with hikers interested in relaxing in or around the town for a few days after achieving their primary goal of completing the trail.
The walk itself does require a moderate level of fitness, and of pre-planning, given the relative thin-ness of infrastructure. We consistently underestimated our water and snack provisioning. I was also grateful for my hiking poles, especially on the hillier sections (though Brendan managed fine without them).
The ideal time to undertake this trek would either be late Spring (April-May) or early Autumn (September-October). It would be quite challenging in either extremes of heat or any kind of rainy weather.
While Tuscany is generally very well-served with accommodation and eating options, the first 30 kilometre stretch across the Crete Senesi in particular is surprisingly bereft of both of these features, and – with the welcome exception of Asciano – you’ll struggle to find anywhere open at all if you miss lunchtime, so you need to choose and time your pit-stops with some care. Despite my worries in advance, all our hosts efficiently organized the daily transfer by taxi of our bags for an average cost of around €50 (La Terra’s owners generously delivered them for free with their own car).
The fact that it’s only just been launched as an official route does mean that the route is generally pristine and very quiet – but also sparsely documented in guidebooks, especially in the English language. This, coupled with the sometimes-haphazard placement of the waymarks, makes it easy to wander off-track in places.
But you will gain a whole new perspective on this region, a great sense of personal achievement, and a significant toning of your calf muscles.
Article and Photographs © Nick Kelly, 2022
Nick Kelly, Dublin, Ireland, 13/04/2022 08:41:28

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