While Amsterdam is by all accounts a fabulous city, the winter weather in the Netherlands could break even the most stoic among us. Needing a break from the gloomy gray skies and relentless misty drizzle, we started investigating where we could do a “workation” – somewhere we could remote work for a week or so and get some winter sun.
From what we’ve seen, it seems like most Europeans opt for either skiing in the Alps or sunning themselves on the Canary Islands this time of year, leading to some pretty eye-popping prices.
As we poked around on Google Flights, round-trip flights to Athens were only 70€. The weather forecast wasn’t necessarily warm, per se– mostly in the 50’s Fahrenheit, but at this point, anywhere with the sun icon on Apple Weather would do!
Ultimately, we decided a better location for some winter R&R would be one of the (many) Greek Islands. We ended up opting to spend 2 full days in Athens at the end of the trip and a week on an island, working during the day and enjoying the sun. But how to choose???
Indeed, it was certainly a bit of a daunting choice, with so many islands to choose from. To save you some time, we’ve combined all our best Greek island winter tips and our thought process in this post.
Luckily, Tegan has a Greek coworker, who gave us some tips for choosing a Greek island in the off-season.
- Tip #1: Check the ferry schedule, as it’s seriously limited in the winter.
- Tip #2: Don’t go too far from Athens, as most of the fast ferries only run in the summer. This leaves you with the slow ferries, which (at risk of stating the obvious) are very slow!
- Tip #3: Go where the Athenians go. Many Athenians have “weekend homes” (what a dream) on an island, and some go year-round if they live close enough. Islands like Syros, Tínos, Aegina, or Hydra are a good bet for this reason.
- Tip #4: Stay in the “chora”, or main town. Many of the smaller towns are completely desolate in winter, with nary a grocery store even open. Even if you can get a ferry there, a week in a ghost town in January is not bound to be a very fun experience.
- Tip #5: Make sure your accommodation has heat. While it’s not snowing by any means, it’s definitely not hot in the wintertime. Having the option of turning the heat on is for the best. We didn’t even end up using ours, but it gave us peace of mind to have it.
With these handy tips in mind, we browsed options on Airbnb and landed on Syros, the capital of the Cyclades. Its chora, Ermoupoli, is populated year-round because of its capital city status, and one Blue Star ferry arrives and departs from there each day.
The same ferry also serves other islands in the Cyclades, stopping first in Syros and then going on to Tínos and Mykonos. We found a lovely apartment on Airbnb that cost a measly $200 for the week, and we were in business!
While we considered Mykonos, it was quite a bit further away and much more expensive– that summertime hotspot status definitely bleeds into the winter season! Tínos is also lovely, but way too small to spend a full week, so we did a half-day trip over there to check it out instead. But more on that later 😉
Note: Second place for us was Hydra, in the Saronic Islands. It’s much closer to Athens but much smaller, and there weren’t a lot of accommodations available.
So the decision pretty much made itself– we were off to Syros for our Greek Island winter workation.
Getting to the Greek Islands from Athens
The ferries to the Greek Islands take off either from Piraeus or from Rafina. Piraeus is the obvious choice in the wintertime because of the ease of access directly from the Athens airport.
However, apparently a lot of people prefer Rafina in the summertime because it’s a lot quieter and more manageable than the “universe-upon-itself” that is the port of Piraeus.
Needless to say, we took off from Piraeus, so that’s where we headed when we hopped off the plane.
It’s super easy to get to Piraeus from Athens on public transit:
- When you exit the baggage claim, follow the signs for “trains.”
- Turn left as you exit, go up the stairs (the Sofitel hotel will be on your right) and enter the signs for the parking garage.
- Take the moving walkway until you enter the train area, where you can get your ticket or ask for help.
The tickets from the airport cost a flat-rate 9€ per person. Simply purchase your ticket, swipe into the platform area, and board the train going to downtown Athens. This can be a bit overwhelming because the signs are only in Greek, but don’t panic– just ask someone which platform to go to.
Helpfully, the airport is the terminus of that metro line (the blue line), so you technically can’t go the wrong way 😉
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You’ll be on the metro for about an hour, taking it from the terminus at the airport to the terminus at Piraeus. You’ll pass all the way through downtown Athens, passing hotspots like Monastiraki, Syntagma, and Plaka.
There are 2 metro stops in Piraeus– check which one your hotel is closest to, and get off there. You’ll have to swipe your card again to exit, and then walk over to your hotel.
There are loads of accommodations in Piraeus, and many are quite inexpensive. Our hotel, Piraeus City Hotel, was extremely bare-bones but clean, and cost only 35€ for the night– perfect for our purposes. We grabbed some spanakopita to go to the nearby Bread Factory, checked in for our ferry, and got everything ready for the next morning.
Finding your Greek Islands Ferry
As we said before, the port of Piraeus is not exactly for the faint of heart. For one thing, it’s absolutely massive, with several “gates” populated by behemoth boats. The gates aren’t always well-signalized, and are fairly spread out from one another.
Here are a few tips to make your check-in a bit smoother:
- Double-check your departure time. Between when we booked and when we departed, the ferry schedule changed by 45 minutes on both ends. We did not receive email confirmation or anything about this, and we absolutely would have missed both boats if we hadn’t double-checked on the Blue Star website. With ferries only running once a day… this would have been far from ideal.
- When you check in for your ferry, it’s crucial to take note of which gate you’re departing from– this place is like a massive airport, on steroids. The Blue Star ferries were all departing from E7 as of the writing of this post, near the Blue Star corporate office.
- Be sure to read the fine print when you check in. There, we found out that we were supposed to arrive 1 full hour before departure, and that N95 masks were required to board and must be worn at all times. By the way, this was still the case in January 2023, despite mask mandates seeming to be a thing of the past. We saw some folks get denied boarding due to this, and it’s definitely enforced.
- While the receptionist at our hotel told us that half an hour before boarding would be a fine time to arrive, we’re really grateful we left with plenty of time. The port is huge and a bit chaotic to navigate, and we had a hard time finding the gate. Our return ferry to Piraeus actually left a few minutes early… which would have been quite bad news for us if we’d been running late.
Once you reach the port area:
- The easiest way to navigate is to enter the port at whatever gate is closest to your hotel (in our case, E9), and follow the maroon-colored pedestrian walkway as it winds around the various gates.
- There are a lot of cars, taxis, 18-wheelers, and general chaos going on, so it’s good to stay aware of your surroundings.
- Once you find your boat, approach anyone wearing a yellow vest and they’ll point you in the right direction. There were a bunch of cars entering the lower part of the ferry, but if you’re just walking on, there’s an entrance on the right side.
- Your ticket will be scanned, mask verified, and you keep going upstairs. There are standard seats, a café with more seating, or you can go outside. We booked our tickets with Direct Ferries and it was a super seamless transaction– check out their widget right below to get started or for Blue Star service directly here.
DirectFerries booking widget
Since the fast ferry wasn’t running, it took us almost 4 hours to get to Syros from Piraeus. The time goes by quite quickly on the boat– you can purchase Wifi, or just download some books or admire the gorgeous blue waters.
Tip: you can bring on whatever food you’d like, so we definitely recommend packing lots of snacks and water. The food at the café wasn’t super appetizing and was quite expensive.
When you arrive at your island of choice, everyone files off the boat, and it departs again a few minutes earlier.
It’s certainly a well-oiled machine, and once you get the hang of it, an easy way to travel.
For our tips on what to do in Syros in the wintertime, check out our guide to Ermoupoli, Ano Syros, and Tínos. For planning the perfect trip to Athens in combination with your island escape, we’ve got you covered as well with our 2-day Athens guide. Keep an eye out for Thessaloniki, coming soon.
You can save this guide for later by clicking on either of the photos below, and as always, check us out on Instagram!
