Day Walks around Cortona

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caspin journeys
Cortona - Monte S. Egidio - Le Celle

This walk takes us NNW of the city. Leaving through one of the city gates, we continue towards the top of S.Egidio enjoying superb views of the valley below, before descending through typical Mediterranean vegetation to end our walk at the Celle hermitage, a slender group of stone buildings founded by St Francis in the 12thC, a spectacularly set, spiritual place.

Walking - 3hrs moderate


Cortona – Madonna del Bagno - Pergo

This walk takes us SSE of the city. With views opening onto the beautiful valley below and surrounded by horseshoe shaped hills, we walk along the contours to reach the remote medieval church of Madonna del Bagno. We then descend gradually to an area of Pergo called La Dogana, meaning customs, the border between the Papal States and the Grand Duchy of Tuscany.

Walking - 3.5hrs easy-moderate


Cortona - Tecognano - S.Angelo

This walk takes us SSE of the city. A gradual downhill trail leads us into a sleepy world of scattered farmsteads and elegant country villas surrounded by cultivated farmland, olive groves, formal gardens, pine copses and woods. On a promontory sits a tiny chapel and in the bottom of the valley the 9thC single nave church of St Angelo.

Walking - 2hrs easy


Ossaia - Tuoro - Isola Maggiore - Passignano sul Trasimeno

We continue along the ridge until we begin our descent to Tuoro and the ferry, which takes us to Isola Maggiore. From its picturesque fishing village we take a circular walk of this peaceful car-free island enjoying wonderful views of the vast expanse of the lake and of our final destination Passignano sul Trasimeno, a bustling lake shore town with many lakeside cafes.

Walking - 4hrs moderate


Ossaia - Sepoltaglia - Piazzano

We continue along the ridge until we reach Poggio Capanna and begin our descent with ever changing views of Cortona down to Piazzano in the val d ‘Esse the erstwhile private hunting grounds of Cardinal Passerini, right hand man of the Medici family and especially Pope Leo X.

Walking - 4hrs moderate


Ossaia - Gosparini - Passignano sul Trasimeno

We continue along the ridge towards Monte Sorbena and Monte Castelluccio until we come out onto a large meadow. A 17thC milestone marks the borderline between Tuscany and Umbria. At the junction of Gosparini we once again have magnificent views of the Lake Trasimeno as we enjoy our lunch at the local trattoria before continuing to Monte Castiglione and then descend to the bustling lake shore town of Passignano.

Walking - 5hrs strenuous


Rocca di Pierle - Molino di Bordone - Montanare

On the other side of the Val di Chiana , between Cortona and Mercatale, lies the Val di Pierle with its imposing Rocca castle. Built in the 13thC by the dominant Casali family, this is the start of our walk. We begin climbing through oaks and chestnuts, prime places for wild boar & porcini mushrooms. At the top of the hill we are rewarded with impressive views of the two valleys and Cortona in the distance. We descend into the Val di Chiana enjoying views of its vast plain, stopping for lunch at our 17thC Tuscan mill.

Walking - 3.5hrs moderate-strenuous




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