Syros, The Best Greek Cyclades Island to Visit in Winter

Few people visit the Greek islands in winter because it’s typically cold. But the lack of tourists presents great deals and a different kind of romantic feel. Many businesses shudder their doors for the season, often heading back to the mainland or focusing on renovations. A hotel proprietor in Mykonos told us that “many business owners enjoy spending winter in Thailand because it is cheap and warm.” So if you find yourself in Greece during this time, the Best Greek Cyclades island to visit in winter is the capital of Syros.

Most Hotels and Restaurants in Mykonos Are Closed in Winter

If you also stay in Mykonos in winter, like we did, it is virtually deserted, but you’ll still pay higher prices for accommodation because it’s the island that adorns the walls of Greek restaurants world wide, and is the name sake of many of them. We paid more for a run down hotel room in Mykonos with a view of concrete, than we did for a lovely little apartment in Syros, with a wonderful view of the town and harbor. And Syros is equally beautiful to Mykonos, and in winter it’s a better mix of relaxed, but with more businesses open.
Sunset on the capital town of Syros, best greek cyclades island
Sunset in Syros

Syros’ Capital of Ermoupoli

The town of Ermoupoli is not just the capital of Syros, but the administrative capital of the entire Cyclades island chain that includes Mykonos, Tinos, Ios, Paros and Naxos, to name a few of the 220 islands. This means that unlike Mykonos town, Ermoupoli is a fully functioning small town of 13,400 inhabitants. It’s the perfect balance of size and relaxation, with enough restaurants, cafes and bars to keep a happy couple occupied for several days. Ermoupoli is arguably even more beautiful than Mykonos’ main town of 9,300 residents because the town sits atop a higher mountain and is more colorful, while offering a similar view of the neighboring islands. Far off in the distance you can see Mykonos from Syros, along with nearby Tinos. When ferries are more frequent, it’s easy to island hop over for Mykonos’ famous summer night life, without having to overpay to stay there.
Shore of Syros, best greek cyclades island

Syros as a New Year’s Destination

We planned to spend New Year’s in Mykonos but were advised that Syros was the far better option. So we rented an apartment for 4 days and had a great time exploring the island and town. New Year’s eve in Syros was a strange sight and we were forewarned ahead of time. Greeks like to spend midnight with their families. It’s only afterwards that they go out. So all the bars were shut before midnight, with only a few restaurants remaining open. We found a small restaurant to open the new year and had a lovely meal with warm Greek style hospitality. Bell asked for a rakomelo, which is basically warm grappa with honey and spices, and frequently found in Greece. While it wasn’t on their menu, just after midnight, the proprietor brought us some free of charge, as she had tracked some down from a neighboring taverna and exclaimed “Kali Xronia!” (literally “Good Year” in Greek and what is said by everyone who wishes you well for New Year’s).
View of Syros from the pier, best greek cyclades island
View of Syros from the pier
We left the restaurant at 12:30am and found a bar in the main square that had just opened for business. It was quiet when we arrived and we found a table next to the large window, with a great view of the excitement in the square. By 1:15am you could barely move inside and we were extremely lucky to have seats. Most people were well dressed and the vibe was festive. We stayed until almost 3am and moved to another bar on the opposite side of the square. By 4:30am the party had faded but was still going, comprised of virtually all locals. But we were fully spent and headed back to our apartment. The island had beaten us.
Bell ringing in the New Year at a packed bar in the main square of Syros, best greek cyclades island
Bell ringing in the New Year at a packed bar in the main square of Syros.
Bell and I both agree that our New Year’s in Syros was one of our all time favorites. Unless you’re in your early twenties, it beats a night out in Ireland which gets far too sloppy well before midnight. But that’s a whole other story as Ireland is also a fantastic place to hang out, it just happens that we currently live here.
Sunrise from our lovely little apartment in Syros. best greek cyclades island
Sunrise from our lovely little apartment in Syros. Not bad for €27 per night.
It’s also worth noting that Mykonos gets very crowded in summer, and its prices are higher than anywhere else in Greece. So for some, Syros would be one of the best Greek cyclades island to visit no matter the season.
Syros, best Greek Cyclades island
Playground in front of a Greek orthodox church in Syros, best Greek Cyclades island
Playground in front of a Greek orthodox church in Syros 🙂

Where to Stay in Syros?

We usually find that offers the best hotel deals, especially in Europe, but even in North America. If you’d prefer to stay in an apartment over a hotel and have never used Airbnb, sign up here and receive credits off your first stay! Be sure to book places with consistently good reviews for the best experience!

More on the Greek Islands

There are so many wonderful Greek islands, but two other favorites of ours are Naxos and Crete. Read why Naxos has long been a favorite island of Greek tourists, that has recently become more popular with international visitors. Crete is the largest island in Greece, offering excellent value in the winter too. Chania is a major highlight, featuring one of Greece’s best culinary scenes, in a charming town that was previously occupied by the Venetian and Ottoman Empires.

Travel to Syros Cheap

Play the credit card points game and use bonus point sign-ups for free plane tickets! There’s a wide variety of banks offering bonus point sign ups that equate to free plane tickets. These days we rarely pay for international flights. If you have questions on travel hacking, leave a comment below or get in touch with us. We’re happy to help! Greek village pin for Pinterest Have questions or something to add on travel in Greece? Leave a comment or email me at [email protected] and I can assist you! 

About the Writer and this Website

Alex Kallimanis is a UCF graduate who grew up in the Orlando, Florida area before living in destinations like Australia, the Netherlands, Ireland and east coast destinations like Boston and Washington, DC. As a travel journalist and travel consultant, I enjoy assisting readers with getting amazing experiences and value from their trips. I’ve visited 58 countries and counting. Alex working on his computer along the beach in Sanibel Island, Florida I’m also a Greek citizen that has made 10+ trips to Greece. My wife of nearly 17 years, Bell, is an Australian scientist working in cancer research. We first met in a hostel in Brugge, Belgium while backpacking Europe solo after college. You can read more on that story in our about page if you’re interested. I encourage you to browse some of the other destinations we’ve covered for helpful tips. I also share advice in our resources page that could save you thousands on travel costs! Disclosure: This article contains some affiliate links. We receive a small commission when you book or sign up through certain links and it costs you nothing extra. Thanks for supporting independent travel journalism during these challenging times for the industry. 


  • Alex&Bell

    Alex and Bell originally met while solo traveling after finishing university in 2002, in Brugge, Belgium. Alex grew up in the USA and Bell hails from Australia. During our nearly 20 year marriage we've lived around the world, including spending six years living in the Netherlands and Ireland. We have traveled to nearly 70 countries and enjoy giving readers authentic and quality travel tips. Alex is an award winning travel journalist and travel planner, who also freelances for other outlets. Bell is an award winning PhD scientist who currently works for a non-profit lung cancer advocacy research organization called Lungevity. Happy travels and if you have any questions leave a comment or drop an email!

6 thoughts on “Syros, The Best Greek Cyclades Island to Visit in Winter

    1. Haha, we probably saw more olives than gold, but they probably bust out more gold to sell when summer rolls around 😉

    1. I think Syros is a great place to take kids! It has a warm family friendly vibe and is not so expensive. And indeed Mel would love it! 🙂 For some parents the beaches in summer might be an issue because they would be topless. But the vast majority would be no more risque than South Beach in Miami, so that would be your gauge on comfortability.

  1. i recently visit Syros, it was planed to visit Mykonos instead but due to the waves our captain decide to visit Syros. Believe me it is a great and lovely place, not expensive. Nightlife is awesome.

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