The capital of the Cyclades, Syros (Σύρος) lies 78 nautical miles southeast of Athens in the breathtaking Aegean Sea. With about 20,000 inhabitants, the island is well-populated and seen as a center of culture and civilization, first occupied over 5,000 years ago by the Bronze Age Kastri civilization.
Its capital and premier port city, Ermoupoli, was built during the War of Independence in the 1820s by refugees from other islands fleeing the war. For a time, it was seen as a more significant port than Piraeus!
About a half-hour walk from Ermoupoli is sophisticated hilltop Ano Syros, which dates all the way back to the 13th century Venetian times.
Only about a half-hour away on the slow ferry is cute as a button Tínos, which is easy to pair with Ermoupoli and Ano Syros while you’re visiting. Just make sure to check those ferry timetables extra carefully!
It’s easy to get to the Greek Islands from the port of your choice. If you’re coming from Athens, that will likely be Piraeus. We used Direct Ferries to book our tickets and it was a seamless experience. You can book with their widget that we’ve embedded below or directly for Blue Star service here.
Know Before You Go
A few things to keep in mind as you plan your trip:
- Tap water is not potable on most Greek islands, Syros and Tínos both being examples. Prepare to purchase many large bottles of water to drink and cook with because the tap water is not drinkable.
- The sewer system is extremely delicate, so you can’t flush anything down the toilet anywhere– including toilet paper. All bathrooms have trash cans next to them to place your toilet paper.
- Water in general (even the tap water) is a precious commodity, with limited hot water available, so prepare yourself for very short showers.
- Many restaurants will automatically bring you a big bottle of water and a basket of bread with your food. We noticed a lot of people complaining about this on Google reviews, but usually it’s only a 2€ or so surcharge, and you need to drink bottled water anyway… so doesn’t really seem like something to complain about particularly, but it’s a good thing to know.
- While the shopping areas and many restaurants are down at the port level, most of the houses, hotels, and accommodations are up, up, up along the winding streets via a series of steep staircases. A previous visitor to our Airbnb counted 110 steps to get to the apartment– and we were only a 5-minute walk from the port. Keep in mind while packing that it may not be the best call to bring a huge rolling suitcase– backpacks are best.
With that in mind, here are some tips for things to do in lovely Ermoupoli, Ano Syros, and Tínos– all packed with kitties, restaurants, waterfront views, and Greek charm.
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What to Do in Ermoupoli
You can likely do everything you need to do in Ermoupoli in a few hours, which is what makes it so lovely to spend more time in, particularly if you’re doing a “workation” like we did.
We were easily able to see all the sights (more than once), and also unwind over Greek coffee, people-watch along the waterfront, and meander through the winding streets, admiring the neoclassical architecture in a variety of pastel shades.
Here are Ermoupoli’s can’t-miss attractions:
- Explore the Municipal Palace in impressive Miaouli Square, as well as the neat Archaeological Museum and Cycladic Art Museum nearby
- If vintage machinery is more your style, check out the Industrial Museum, housed in 3 former factories
- Marvel at the Apollo Theater, modeled after La Scala in Milan
- Check out the waterfront “Little Venice” area with shops and restaurants
- Visit the Vaporia Quarter and the beautiful Church of Saint Nicolas (Agios Nikolaos), the patron saint of the island
- Speaking of churches, the Church of the Assumption of Virgin Mary has a holy icon of the Virgin made by the painter El Greco
No one would blame you for feeling a bit peckish after all that walking, and Ermoupoli has great restaurants and cafés in spades. Extra-lucky for us, many of the city’s residents are year-round residents, so most everything is open in the wintertime.
Here are a few places we loved:
- Traditional Greek food at To Tsipouradiko tis Myrsinis (Το Τσιπουράδικο της Μυρσίνης). Absolutely massive portions, nice service, and beautiful waterfront location.
- Hip cocktails at Barrio or Espiritu.
- Quick to-go lunch and vegetarian/vegan-friendly options at Street Food Stories Syros, or pasta to-go (what a concept!) at Kings of Pasta.
What to Do in Ano Syros
Most known for its stunning Cathedral of Saint George, Agios Nikolaos church, and the Monastery of Agios Ioannis, you can see all the way to Paros and Naxos from its viewpoints on a clear day. Even if it’s a bit overcast, you’ll still get stunning views of the South Aegean below.
Climbing up to Ano Syros gives you a totally different vibe to Ermoupoli, namely, one that is much more medieval and Catholic in character due to its Venetian origins. Its courtyards burst with bougainvillea even in winter, and its pastel-colored, whitewashed houses are simply adorable.
While it’s certainly quiet in winter, it’s a lovely place for some contemplation and a bit of cardio to work off all those Greek sweets and cheeses you’ll certainly be indulging in.
Speaking of, to get to Ano Syros from Ermoupoli, simply walk up, up, up until you can’t go up any further. A winding road will give way to a jumble of narrow, steep steps, as the houses below get smaller and smaller in the distance
What to Do in Tínos
Located about half an hour from Syros on the slow ferry, Tínos is absolutely charming. While perhaps more traditionally “cute” than Ermoupoli, its main city, Tinos (or Hora) is much, much smaller and less touristy. We visited for a half-day and had more than enough time to see the sights there.
It merits mentioning that, if we had visited in summer, we would have loved to stay on Tínos– particularly to check out its other towns like Pyrgos and Panormos. But ultimately, we’re glad we chose to stay in Syros rather than Tínos for the week in the wintertime. That said, the main port area on Tínos is a marvelous day trip year-round.
If you decide to go, don’t miss:
- Visiting the iconic Panagia Evangelistria (Our Lady of Tinos), one of the most important churches in the Greek Orthodox tradition, visited by thousands of pilgrims each year who crawl up to the church on their knees
- Checking out the religious items for sale along Megalochari Street as you trek up to the church
- Exploring the adorable whitewashed cobblestone streets of the chora, or main town area
Trying Tínos cheese and other local treats at its many restaurants. We had a fabulous lunch at Malamatenia near the port.
We had a lovely “workation” in Ermoupoli, and really enjoyed spending some time on the Greek Islands during the winter off-season. We’re eager to go back in the summertime to see what all the fuss is about, but winter is a lovely, calm, and serene time to visit for some R&R, great food, and bottom-of-the-barrel prices.
For more Greece content, don’t miss our guide to a winter visit to Athens, and keep an eye out for Thessaloniki, coming soon. In case you missed it, our Greek Island Winter Guide has all the best tips for navigating the Greek Islands in the off-season.
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