I first saw the distinctive twin peaks of Ermopoulis on my first trip to Greece in 1981, but did not land at Syros until autumn 1991, and that landing was unintentional. I was storm stayed on my way from Naxos to Piraeus (and eventually missed my flight home). I went back to Syros in spring 1995, again I was initially storm stayed and decided to stay on until the first day time ferry to Naxos (having kept my landlady up until gone midnight when I was initially storm stayed, I did not want to arrive in the middle of the night).
In 1995 the huge breakers I saw from the plane were an ominous sign.
I arrived on Friday night, and stayed until a hydrofoil left for Naxos on Monday afternoon. The first night I stayed at the Hotel Diogenes, a very smart hotel in a pleasantly restored old building, with "sanitised" stickers in the bathroom, a mini-bar, matching bedspreads and curtains. It was all very plush - and expensive, but not my idea of Greece. Next morning I went out to look for alternative accommodation, and I was seduced by the kittens at the kafeneion 'Apollon'. The kafeneion owner carried the kitten inside and fed it a huge piece of fish.
Whilst at the kafeneion we were approached by a a large, lanky, tan-coloured nondescript one-eyed dog called Raki. When I left Raki followed me. I found rooms at the nearby 'Pension Dioskouri', run by Maria …(I never discovered her surname), aided by her husband, and abetted by Raki, the dog who acted as room tout. Pension Dioskouri caught my attention because of the first floor loggia style balcony overlooking the road. Inside it was an old -fashioned (but clean and comfortable) nineteenth century house, with rooms off the loggia and off the central hall cum sitting area, with arm chairs one of which was invariably occupied by Raki (when he was not lounging in the loggia). Each time we went in we smelt a slight smell of wet dog (the storms continued, and we squelched our way round Syros). From the loggia we heard a strange repetitive noise, and later found that we were living above a printing press. [NB On a later visit to Syros I spotted the building we had stayed in, but the building was no longer a Pension.]
Why were both my visits to Syros the result of being storm stayed? Before I saw Syros at close quarters (rather than from a ferry) I had imagined it being something like a smaller version of Piraeus, that is not very attractive. Syros is attractive, but in its own way. It is large, and definitely a town, almost a small city with large west Eupopean city sized buildings. In the mid nineteenth century Syros was the most importanrt port in Greece. A relic of this is the number of large houses there today. The centre is old world Greek without any tourist tweeness, a workaday town for workaday people. Out of the centre are relics of Syros's ship-building past, huge numbers of collapsing and decaying Greek Victorian type buildings. I found these areas of historic interest, and hope that something can be dome to arrrest the decline of these once beatiful buildings; others may find the decay depressing. The crumbling buildings are a sorry sight - but show what a grand place Syros must have been in its heyday. You need not venture out as far as the ruins, the town is not crumbling in the centre. A small scale city feel. Pleasant. Makes Naxos feel provincial. Less tourist dominated that otther islands. A pleasant 'Greek' town. [NB On a later visit I noticed fewer old buildings. Some restored, others demilished, I suspect. Or perhaps the place looked less derelict when it was not saturated with rain].
The main 'market street' , Odos Hiou, was particularly pleasant, lined with food and other shops. One fishmongers (always popular with cats) had fish displayed in an old boat. The shops were small and old-fashioned. This street led to the main square dominated by the large town hall. Off market street I found an excellent wine shop with a very helpful and informative owner. I also found a number of bookshops.
Being lazy, I caught a taxi up to Ano Syro, visited both the Catholic and Orthodox cathedrals, and walked down. Walking back down to the harbour I realised just how extensive Ermoupolis must have been in its heyday such is the area that the built up (or once built up and now crumbling) area covers. Up in the hills of the town you can find something of the atmosphere of a Cycladic village. Downhill the atmosphere is more that of a non Cycladic town, but pleasant nonetheless.
I went by bus to Dellagrazia (alias Posidonia) where there are a number of large nineteenth century country houses, presumably built by ship owners. One surprising feature by the roadside was a red British K6 type telephone box! I walked round to the fishing village of Finikas. I had hoped to do a circuit of Syros by bus, but the bus I caught back came by the same route as I had gone out on.
Don't stay in Syros town if you want a 'typical' Cycladic village (though you may find the uphill areas more to your taste) but enjoy it for what it is. Different, with a charm all of its own.