Cortona is an interesting old city to explore, and doing so, I have discovered some places that I would like to pass on to future travelers. Having become quite popular for the Hollywood movie ‘Under the Tuscan Sun’, it is for other reasons that I have come to enjoy this destination. Here are 7 free things to do in Cortona Italy and an extra little adventure for a small fee.
Walk to New Cortona
One of my favourite things I did within the first few days of arrival, was walk down the hillside to the new part of Cortona. Now it’s not the city that is of interest, but the 40-minute walk through terraced ancient olive orchards and farmland. Start your journey at Piazza Giorgio Amendola (link here) and take that sharp turn to the left, immediately heading down the hill beside a stone wall.
Along the way find incredible viewpoints and a most amazing place, an Etruscan tomb called Tanella Angori. Dating from the 2nd century BC, one senses mystery here, standing in this ancient place.
If you can steel your gaze away from the views, notice the various types of cacti, medieval stone walls created by the farmers and of course the beautiful flora all around.
Via Jannelli
In the old city of Cortona is the most amazing and historical street called Via Jannelli. The medieval brick and timbre houses that were constructed in the 14th century survive virtually unchanged. This street is precious and is situated on the lower side of the main square called Piazza delle Repubblica. Feeling like I have stepped onto a movie set, this architecture is stunning to see. People are still living in these homes and in fact, one is even for sale!
Public Park
There is a walking park in Cortona that is the prettiest oasis to discover. In fact, its regularly filled with locals, families out enjoying the sunshine and spending quality time together. The park doesn’t seem to have an official name, instead it is a road called Viale Giardini Pubblici on Google Maps.
For a long stretch, several kilometers if I had to guess, it is a wide gravel path. A small church rests at one end that is beside an area full of shade trees, fountains and statues. Part way down is a playground and an amphitheater.
All along this beautiful promenade are benches and the most incredible views over the Tuscan valley below. The other reason this park is so wonderful? It’s the only flat piece of land up here on this hilltop, so a pleasant respite from the up and down of walking stairs and traversing hilly roads.
Stone Village
One of the areas of Cortona that I really enjoy is not the central, tourist heavy, main streets and square, but rather up behind that. It’s a neighborhood that feels like a distinct space, a village perhaps. Walk up the hillside away from the main square, towards the fortress, past the Convento di San Francesco. It is these old stone streets that you will find yourself having time travelled back to medieval ages.
There are several things to see while exploring this small area. An 18th century shrine nestled into the corner of a courtyard, depicting Sant’Antonio Abate with a pig at his feet and a skull on the table. A large and ancient well, peek in through the holes in the wooden door to see inside.
And the doors, medieval wooden ones, with fantastic old hardware and Florentine coats of arms engraved into the stone above them. Marvellous! Such an enchanting area to explore.
Church of San Niccolo
A most exquisite and humble church, constructed in 1440 that is tucked into the old village just above the central core of Cortona. It is privately run now, so opening hours can vary. Not much to see from the outside, but the interior is stunning.
Neither grand nor fancy in the traditional sense, but astonishing that almost the entire thing is painted, even the coffered ceiling. Go behind the altar into another room, filled with the treasures of the parish. These items are still used once a year in a procession on Good Friday. Having visited my share of ornate and extravagant churches, it is these little ones that intrigue me the most now. A small donation may be requested upon entry.
Saturday Market
If you happen to be in Cortona on a Saturday, you must visit this little market. Full of travelling vendors who have arrived into the hilltop town with their trucks, it’s when the locals come out to shop.
Find porchetta, loads of amazing cheeses, fresh produce, clothing and the best olives and preserves. Located in the Piazza Signorelli it is the perfect place to sample Tuscan specialties, people watch and learn about local and authentic products.
Cimitero della Misericordia
Normally I would make a separate post about the cemetery I visit in each destination I travel to, but this one is too small. Even still, it is not to be missed. One can see it form part of the picturesque scene when standing at the edge of town. Its stunningly beautiful.
Walk down the hillside, perhaps only 10 minutes from the old city gates, and you will have arrived. The main portion contains many above ground sarcophagi that resemble ancient Roman ones almost exactly. I have never seen this before and am quite intrigued.
Around the back and down below is the crypt, a beautiful and quiet place to explore with amazing views down into the valley. When you walk back towards the entrance, don’t miss looking up at the old city, it is a lovely vista to behold.
Fortezza di Girifalco
This one is not free, however for €5 and a steep walk to the highest peak in Cortona, one can visit this 15th century fortress. Built by Cosimo Medici on the site of an ancient Etruscan fort, it was an important stronghold for his Tuscan empire. Left to ruin, it has only recently been restored enough to allow visitors to explore.
The interior section is being used as a gallery and was being cleared out from an art exhibit on the day I visited. But it’s the exterior and walking the walls and ramparts that you really want to experience.
The views and seeing the main structure of the fortress, its medieval architecture and size is amazing. Do mind the signs to be careful and not get too near the edges. Once you are up here, the Basilica of Saint Margaret can be your next stop and the convent right beside it, both free.
There has been more to discover in Cortona than I anticipated. While I have not felt as welcome here as other cities I have recently visited, it’s definitely worth a stop. A charming place to study authentic medieval architecture and be close to that ever-beautiful Tuscan landscape.
