Evaluation: This is the longest, but probably the nicest hike you can make on the island of Sýros. An advantage is that you can start from Ermoúpoli - this hike is a succession of the red-white hikes no. 1, 2 and 3 and the green hikes no. 1 and 2. The hike brings you to the acropolis of Kastrí, very famous because of its findings from the early-Cycladic civilisation (3200 - 2000 B.C.). It leads you through a beautiful mountainous landscape and you reach heights of more than 300 m. Basically all the time this hike offers magnificent panoramic views on the wild east coast of the island. Clearly, it deserves an evaluation of ***. 
[Updated by Raymond on September the 24^th, 2014.]

Estimated time: The actual walking time is 1 hour to the hamlet of Richopó (hike no. 1), 30 minutes to Platý Vouní (hike no. 2) and 35 minutes to the valley of Glysoúra (hike no. 3). The climb to the height of Kastrí will then only cost you an additional fifteen minutes (green hike no. 1).
Finally, descending back to the valley and climbing up to Chalandrianí (greens hikes no. 1 + 2) will take a little under 50 minutes.
All together, this makes for a total actual walking time of 3h10, which refers to a full hiking day – the height of Kastrí is of course the ideal picnic spot.  

Route description: (0h00) You depart at the quay, in the centre of Ermoúpoli, at the winged monument in memory of the resistance during the Second World War, situated between two palm trees. On the opposite side, the street El. Venizélou runs straight to the Platía Miaoúli and you can already see the neoclassical dimarchío (town hall) from far away. Beyond the town hall you can also distinguish the large church with two towers and the blue dome – this church of Anástasi is your first aim.

(0h04)After a few minutes you reach the elegant marble square with a lot of pleasant outdoor terraces. In the far right-hand corner, on the left of the OTE building, you take the Merkoúri street, bending to the right until it reaches the Bardaka square with the theatre of Apolloon. You continue on the right of this theatre and you take the slightly rising street straight ahead. In this way, you soon reach the square with the beautiful forecourt, planted with palm trees, of the Agios Nikólaos church, dating from 1848. 

The church of Agios Nikólaos.

When going up the steps you can see the highly situated Anástasi church from the entrance – so you know which way to go now. You take the small street all the way to the left of the Agios Nikólaos church, the Odós Vafiadáki. You pass a few typical town houses and then the street turns into a broad staircase street. After three minutes you take a side road with concrete steps to the left , the Odós Samíou, and at about the highest point of this street you go right, into the Odós Ierou Lochou. This street has a lot of steps and it leads you straight to the highest church – behind you, there is a great view on the harbour. After a steep climb you get to the concrete retaining wall of the church; you go left and then right and then you have arrived. From the terrace with benches underneath the church you have a marvellous view on the entire harbour, the town and the bay. The entrance to the church is on the left side. 

The Anástasi church dominates the whole city.

(0h16) You then take the asphalt road on the far left of the church and you follow this Leofóros Kyprioon Agnoumenoon for about 6 minutes – on the left you have a nice view on Ano Sýros.

Panoramic view over Ano Sýros.

You continue on this windy asphalt road, between the highest situated houses of Ermoúpoli; you keep a little to the left and after 6 minutes you reach a crossing. A signpost points straight ahead to Ermoúpoli, but you take the broad asphalt road on the left. After a couple of minutes already, in a slight bend to the left, you take a gravel road off the right, leading to the chapel of Agios Panachrántos (signpost). The insignificant chapel is closed, but you have a nice view on Ano Sýros.

(0h26) You continue on the gravel road and, at a bifurcation, you should keep to the right (hiking sign Richopó 35’ / Platý Vouní 1h10); very soon you notice the beginning of a monopáti, on the right of a wall – this trail is indicated by means of a red [1] on the wall.

The hiking sign announcing walk [1].

At first the trail runs on the right-hand side of the gravel road, but in a bend of the road, the rocky path continues straight on [1]. You keep going straight ahead and gradually up the hill. After some 3 minutes the trail becomes steeper, running to the left of a wall [1] and you can see how the trail and the wall continue far in front of you. After about 11 minutes, it curves to the left and a little later, you keep to the right on the stony slope – you now proceed above and to the right of the old, overgrown path. Behind you, you can enjoy a beautiful view over Ermoúpolis and Ano Sýros.

Panoramic view on Ermoúpolis and Ano Sýros.

You keep going higher and higher, against the slope and between two walls.
You continue going up, but then the slope gets less steep and Ermoúpolis and Ano Sýros disappear.
The walls diverge and you should follow the right wall, until they converge and you arrive at the top.
Here, the view on Tínos is very nice and to the right, you also can see the islands of Mýkonos, Rhínia and Dílos, Náxos, Páros and Antíparos. You can see some houses and roads in front of you. You descend for a couple of minutes until you arrive at a couple of white houses and a small white chapel – this is Richopó.

(1h00) There is a sign pointing to the cave of Ferekýdis and from now on, the path is signposted with a [2].
Past the houses you continue by keeping more or less to the right, between walls. The following trajectory is very beautiful: you go down on the right-hand side of some steep rocks and you have a great view on the sea and the islands of Tínos and Mýkonos straight ahead – sometimes, the path is paved. 

The monopáti to Platý Vouní.

(1h13) After 10 minutes you get to a steep descent and you can see the continuation of the trail in front of you. You now get to a difficult stretch, because of the rubbish and all the plastic that is strewn on the path – it comes from the refuse dump that lies down to the right – a real shame!

The rubbish on the path! 

When you arrive almost down, you find a sign pointing to the cave on the left and there is also a narrow trail going up on the left – there is nothing to be seen on that side, though. The beautiful and sometimes paved trail continues and after 4 minutes you get at the top and in front of a valley – on the other side you can see some houses again.
You can take some rest here and – in contrast with what you saw a few minutes ago – enjoy the splendid views: on Tínos, Ystérnia and Kardianí are clearly visible, and you also can see Andros (to the left) and Mýkonos ans Náxos (to the right).

You now get to a beautiful and sometimes paved stretch.

The path to Platý Vouní. 

Your trail continues to the left and it runs around the entire valley; almost down, you veer to the left and after 16 minutes you arrive at the bottom of the valley, in the bed of a dried up river and near a large water tank. The path continues to the hamlet: first, there is a difficult gate, but then you proceed straight ahead through the houses. The street becomes paved and you pass a house with a blue water tank – some 20 metres further down you find a small paved street off the left – there is also a red-white trail marker [3] on the wall. Very soon the street turns into a really nice trail.

(1h34) You now walk past some beautiful little vineyards and after 2 minutes you DO NOT take a left – this path leads to Chalandrianí – , but you continue straight ahead [3]. On a trail that was recently cleared you go down into a bed of a river for a few minutes: you cross it and go up again on a narrow path. After some minutes, you pass through a gate made of a wooden pallet [3]: the path is somewhat vague and continues on a slope with frýgana (little bushes), but in front of you, you can see a more clear and brownish path. But first, you get to a little road, where you take a right for a few moments; very soon, you can take a path to the left, that runs straight to a pole (red mark), and then, the clear brownish path begins.
You arrive between walls and then follow the lower wall. About 7 minutes later, you arrive against a side wall: you take a right for about 20 m and then you go through a wooden gate in a breach in the wall, to the left (trail marker [3] on the other side of the wall). You descend and after 4 minutes you cross a small valley with some reed and even a broken palm tree. In this way you arrive at a white house with a couple of trees and some ruins nearby – this is Psýcha. From here you have a nice panoramic view on the island of Tínos.  

1h56) Just before the white house your trail goes down on the right, but almost immediately you get to a junction, where you take a left. A little further you reach a wall with a wooden gate and the trail continues in the same direction.
You pass through a slight depression, then you go up again towards a small ruin [3]; the trail now leads straight to the beach, and finally the descent is rather steep until you get to the pebble beach of Glysoúra.

While descending to the beach of Glysoúra. 

(2h09) Once arrived down, you continue diagonally to the left and then you start climbing up the steep face of the acropolis of Kastrí, guided by many, sometimes redundant arrows. The first three minutes of the climb are difficult and then you reach a vague junction, where you go up on the right (red arrows). You zigzag up and after a rather strenuous climb you go through a breach in the wall and you reach the actual plateau. You then continue to the left and further up. 

The ring-wall of the acropolis of Kastrí.

At first you walk on the right-hand side of the ring-wall and you keep going higher and higher; you thus arrive at a wooden gate in a wall, with lots of red signs. You should actually go to the far left and upper corner of the rocky plateau in order to get a good impression of the exceptional location of this akropolis, between the deep valley of Glysoúra and Kastrí. 

(2h23) Except for the walls, there are few remnants of the early-Cycladic settlement that used to be situated here, at the time of the early Bronze Age (3200 - 2000 B.C.). On the opposite side of the valley of Glysoúra you can already distinguish the houses of Chalandrianí, your final destination.

[You can see some nice photos of Kastrí on http://www.ou.edu/finearts/art/ahi4913/aegeanhtml/cyintro.html ]

Remains of the acropolis of Kastrí.

On the opposite side, towards the northwest, you have a view on the islands of Andros, Tínos and Mýkonos.

View on the bay of Glysoúra.

In order to descend you first take the same road. You should pay attention to closely follow the red signs, otherwise you might go down too much and you will miss the hole in the ring-wall! You should reach this hole after about 8 minutes. For the next 6-7 minutes you carefully descend into the valley. 

(2h38) At the opposite side of the valley (red dot) you first go up again, but after this steep climb of about 3 minutes you should watch out! In a curve – close to the beginning of the beach – you remember that earlier today you came from the vague trail straight ahead. Now, you go up on the right, following the red trail markers. After about 2 minutes you have to watch out again: you DO NOT go through a breach in a wall, but you follow the obvious trail that takes a left BEFORE the wall (red dots). Some 1-2 minutes later you go slightly towards the left, moving away from the wall. A little further you have to go straight ahead (red dot), but later on you curve to the right and you thus climb up until you reach the wall again. You walk through a wooden gate and the following climb of 7-8 minutes is rather difficult. The panoramic view on the rock of Kastrí gets more and more impressive.

The impressive acropolis of Kastrí.

(2h53) You then go through another breach in a wall and you can now clearly see the houses of Chalandrianí, not too far away anymore, fortunately. The path gets less steep and after another 10 minutes you reach the beginning of a concrete road and a sign pointing to "Kastrí Prehistoric Settlement".

(3h03) You take the road on the far left (so not one of the two roads going up) and you now walk all around the town of Chalandrianí. Some 3-4 minutes later you go straight ahead and NOT to the left.

[The road on the left runs in the direction of Platý Vouní and this would be a possibility to return to Ermoúpoli...]

You keep following the concrete road going up. After 4-5 minutes you arrive at another junction: on the right you could descend to Chalandrianí. In this neighbourhood more than 500 graves were found, often with findings (pottery utensils, jewels, weapons, implements…) from the period 2800 - 2200 B.C.

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