Off-Off-Season on Syros

“Winters on the Greek islands are undeniably brutal, and not something prospective visitors will see pictured in the sunny travel brochures. So, when you have experienced the off-off-season in Greece for decades, and yet voluntarily sign up to spend a month on one of the lesser-known Cyclades, you are either a glutton for punishment or ready to court new experiences; gather in a new trove of memories. The latter was the case when I decided to spend a month on the island of Syros . . . in the middle of the worst winter in 45 years.”—Chiara-Sophia Coyle

Clicks & Relativity

By Chiara-Sophia Coyle

SONOMA California—(Hubris)—1 August 2023—Winters on the Greek islands are undeniably brutal, and not something prospective visitors will see pictured in the sunny travel brochures. So, when you have experienced the off-off-season in Greece for decades, and yet voluntarily sign up to spend a month on one of the lesser-known Cyclades, you are either a glutton for punishment or ready to court new experiences; gather in a new trove of memories. 

The latter was the case when I decided to spend a month on the island of Syros . . . in the middle of the worst winter in 45 years. Absolutely magnificent thunderstorms and once-in-a-half-century snow storms were in store for me, along with gale-force winds and seas too rough for ships. (My PTSD kicked in a few times over the course of my sojourn as I traveled back in time to recall vivid childhood memories of being cold to the bone on Mykonos.)

The sight of the Syros’s port and hills—from the ferry—comprised a very familiar visual, as all ferries traveling from Mykonos to Piraeus make an obligatory stop there. In high school, back in the day, Syros was where we Mykonian teenagers went to participate in athletic competitions with teams from the neighboring islands: three days marked by high anxiety and pressure to “win.” I’d never been back, since. I had no desire to stir up memories of high school athletic events, and of harsh criticism coming at me from all directions. So, from the boat I would always look out at Syros from the deck of a ferry, coming and going, and say thanks but no thanks.

Over the last few years, though, the chatter has been all about how this island was becoming an art and music scene, chock full of “culture.” The history of Syros is rich; the main town a beautiful blend of architectural styles, combining elements of the neoclassical, Venetian, and Cycladic. 

But, above all, Syros is a small corner of Greece still holding its own against the torrents of visitors who have overrun other, more popular Cycladic islands. In other words, on Syros, it’s still the good old days, in stark comparison to Mykonos and Santorini. 

So, one of my best childhood friends and I decided to embark on a one-month trip to Syros, renting a modern Airbnb, and, so, pretty sure we would be warm, indoors at least.

Despite the pandemic’s limiting much of what we could participate in, indoors, in winter, we were convinced that our lodgings and nature outings would make for a memorable experience. Looking forward, as well, to cooking a lot, something we both love (although my friend is a professional chef, which I am not), we set off.

And, though I grew up just across the way on Mykonos, Syros took me very much by surprise!

An island of two faces, perhaps more, with two dominant hills up which the capital rises theatrically, Syros is a stage where the Greek Orthodox and Catholic religions meet and coexist, each claiming its own space and lending the island its unique character. Numerous smaller, humbler settlements scattered across Syros maintain their own distinct visual identities. On Syros, I felt transported once again to childhood memories and familiar countryside landscapes.

I may even have picked up one small rock to bring back to the US as a keepsake and reminder that, while much in Greece has been lost to tourism, so, so much is still alive and well, if you seek it out.

Ano Syros, the hill-top neighborhood of the main town, is an area I visited frequently despite the long uphill climb to the summit. Built during the late Byzantine era, it is a classical Cycladic medieval settlement built up densely with narrow, winding streets, and decked out in all the glory of Greek blue and white. (It reminded me of my hometown, Hora, Mykonos, but 40 years ago.)

I fear Syros will eventually fall victim to tourism; loved to death like so many other Greek islands, but, for my winter memories and pictures from the numerous outings my friend and I took, I am incredibly grateful.

Oh, and if you plan to visit in winter, make sure your heating bill is included in the cost of your rental: you don’t want to end up monitoring the ticking device that tells you, in no uncertain terms, how much your precious heat is costing you.