Hiking Around Cortona: Historic Trails and Panoramic Walks

Cortona is where the trails cross. Perched on the edge of the Valdichiana at 494 metres above sea level ¹, this Etruscan hilltown is the meeting point for pilgrim routes centuries old, ridge paths walked since the Neolithic, mountain loops that look out over Lake Trasimeno, and slow strolls through the olive groves. Trekking around Cortona isn’t one experience but several, and this guide is here to help you pick the right one: a map of the historic routes and of every way there is to explore this land on foot, from the multi-day walk to the hour-long ramble. We write it as people who see these trails first thing every morning. Hotel Villa Santa Margherita — a quiet retreat with a garden and private parking, a short walk from the old town — makes an easy base for setting off at dawn and getting back at dusk without a single logistical worry.

How to choose your trail based on what you’re after

Cortona doesn’t have a single “trek” — it has four families of routes, each with its own rhythm and its own level of difficulty. Before you start hunting for GPX tracks or buying a guidebook, it pays to work out where you fit. The table below is the fastest way to do exactly that.

The great historic and pilgrim routes

This is the beating heart of the place. Some of the most important routes of faith and history in central Tuscany weave together around Cortona, and here walking means passing through centuries.

The most sought-after is the Way of St Francis, the network of paths also known as the Via di Francesco, which passes through Anghiari, Arezzo and Cortona before climbing to the Sanctuary of La Verna, where the saint received the stigmata ². Along the way you meet Franciscan traces in art and in hermitages, starting right at the Le Celle hermitage on the edge of Cortona ². It’s the route with the deepest spiritual charge, and it works just as well for a single stage as for the full multi-day walk.

The Via Lauretana follows an ancient Etruscan-Roman road that linked Cortona to Montepulciano and Siena, later becoming a pilgrim route towards the Holy House of Loreto. The track sets off from Porta Pispini in Siena and reaches Camucia on a lovely walk through the heart of the Chiana countryside — on foot, by bike or on horseback ³. In effect it ties Cortona into the Via Francigena, which crosses Tuscany for roughly 400 km ².

The Via Romea Germanica has revived a very old pilgrim road that once joined Stade, in northern Germany, to Rome, and that passes through Cortona’s territory ³. Together with the Lauretana and the Via Clanis, it’s one of the routes that make the Valdichiana Aretina a historic hub of European pilgrimage ⁴.

Finally there are the historic trails of Roman origin: the MAECparco trail project brings together a network of Etruscan-Roman paved roads running to more than 120 kilometres ³. Walking on those stone slabs means retracing ridge routes that have existed since the Neolithic, with stretches of Roman-era paving still legible underfoot ³. It’s no accident that Cortona turns up in the historic gazetteers under its ancient names, Corito and Curtun ⁵ — a reminder of just how deep the layering of these roads runs.

Climbs and mountain loops across the Cortona ridge

Above the town rises the Sant’Egidio ridge, and this is where a Cortona trek becomes a hike in earnest: real climb, real effort, real reward at the top. These are day routes, to be tackled with proper footwear and legs that have done some training.

The Monte Sant’Egidio loop is the classic. You start from the old town, home to the MAEC, climb towards the mountain along paths with an ancient history, and close the loop by dropping back into Cortona past the Le Celle hermitage ⁶. One of the most complete variants — the loop linking Torreone, the Croce di Sant’Egidio and Le Celle — measures about 12.50 km with 500 metres of ascent ³.

The climb to the Croce di Sant’Egidio is the panoramic goal of the whole ridge. From here the ridges and counter-ridges open up views over the Valdichiana, Lake Trasimeno and the Umbrian-Marche Apennines ³. In all honesty, the busiest ascent — the Alta di Sant’Egidio via Cortona — is also reckoned the toughest in the area, rated 3.9 stars across 12 hiker reviews ⁷. Don’t expect a stroll; expect a hike that earns its view.

CAI Trail 50 is one of the backbones of the local walking network, threading through the Tuscan countryside that rings the town ⁸. For those wanting more, the advanced ridge hikes towards Monte Ginezzo reach routes like the one taking in Monte Maestrino and the Rocca di Pierle, around 11.60 km with 450 metres of ascent ³, or the loop of Portole, Teverina and Falzano, 12 km with 650 metres of ascent ³. The whole Monte Ginezzo area is a Site of Community Importance, protected for its heaths, grasslands and birds of prey — and the wolf has even been recorded here ³.

Spiritual paths and slow walks

Not all walking around Cortona asks for effort. If anything, the note most in tune with the soul of this land is slowness — made of silence, of contemplation, of a pace that eases off among the stones and the olive trees. It’s the side we most love to point our guests towards.

The walks on foot to the Le Celle hermitage are the most requested. Le Celle is the wonderful hermitage that St Francis reached following the route of his travels through Tuscany, accessible along CAI trail 563 ³ — the first convent the saint founded, and to this day a place of peace and nature ⁶. You can get there in under an hour from Hotel Villa Santa Margherita, and the return down the Rio di Loreto valley holds a surprise: along this stream of just 3 km there were, until the middle of the last century, no fewer than 17 watermills, some of them still recognisable today ³.

The Farneta Palaeontological Trail is an easy loop of about five kilometres that sets off from the old abbey and crosses the countryside where important fossil finds came to light. Signage and information panels accompany the walk, which suits families with children and bikes just as well.

The paths through the olive groves are the gentlest way to experience the Cortona hills, between silvery rows and wide horizons, perfect for anyone after a slow journey through fields, woods and meadows ⁹. And right above the walls, the walk through the Poggio quarter offers a short but intense bit of urban trekking, among the stone houses of the town’s highest core. These are itineraries for the early morning or the warm light of late afternoon, and all they ask for is comfortable shoes and a taste for quiet.

Nature, water and landscape along the trails

The land around Cortona isn’t a backdrop — it’s the very reason these trails are worth the effort. The Tuscan countryside around the town lends itself to countless outdoor activities, and trekking is the first of them all ⁸. A short distance from the town a crown of protected areas opens up, from Monte Ginezzo about 7 km away to the Ferretto-Bagnolo woods at 13 km, from Monte Dogana at 14 km to the park and Lake Trasimeno at around 17-18 km ¹⁰. It’s a patchwork of habitats that makes every season different.

Water is a less obvious but captivating thread. Beyond the mill valley of the Rio di Loreto ³, the valley floor offers something altogether different: the Sentiero della Bonifica along the Canale Maestro della Chiana, a flat route of about 60 kilometres, ideal for anyone after a walk with no climbing ³. For those travelling with children, the Palaeontological Trail links the Abbey of Farneta to the Palaeontological Museum over five kilometres that even the youngest can manage, and that work on a bike too ¹¹. Flat stretches like this one lend themselves perfectly to pairing a walk with an e-bike, and the hotel offers rentals for covering the valley-floor distances without breaking a sweat.

When to go and how to prepare

The good news is that Cortona is walkable all year round. Even in winter the Valdichiana Aretina offers hikes along the scenic trails, with the stone villages turning into something out of a fairy tale ⁴. Spring and autumn remain the ideal seasons, with mild temperatures, long light, and blossom or foliage that reshape the landscape. Summer is best met by setting off early, before the heat, choosing routes shaded by woods or olive groves.

Three practical rules apply to everyone. First, be honest about your level, because a ridge loop with 500 metres of ascent ³ is not the stroll up to Le Celle, and reading the times and difficulty of each route before you set off saves nasty surprises ¹¹. Second, get hold of a reliable map, because up on the ridge the phone signal isn’t guaranteed, and the local cartographic guides cover the whole CAI network and the Roman roads ⁹. Third, carry water, trekking shoes and a windproof shell, because at altitude the weather turns.

One last word on atmosphere. Coming back from a walk to find a quiet garden, private parking where your car is waiting, and a terrace looking out over the Valdichiana is as much part of the experience as the morning’s climb. It’s the rhythm of slow travel that Cortona — a town of views facing every point of the compass ¹² — gives back to anyone who crosses it on foot.

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