Astypalea – The Greek Island That Surprised Me the Most
Astypalea. That was the reaction I got from most of my friends when I mentioned my next destination in Greece. A blank stare. Sometimes a polite nod. Once, someone thought I said “Amsterdam”.
And that reaction — that complete lack of recognition — is honestly a big part of why I love this island so much.
I have visited most of the Greek islands by now. The famous ones, the popular ones, the ones everyone posts on Instagram. And after all of that, Astypalea is the one that genuinely surprised me the most. It is the one I keep going back to. Here is exactly why.
Astypalea’s old town at night — one of the most atmospheric views in Greece
Where Exactly Is Astypalea?
Astypalea is genuinely one of the least-known islands in Greece — and it deserves better.
It sits right in the middle of the Aegean, between the Cyclades and the Dodecanese. Technically, it belongs to the Dodecanese — same group as Rhodes and Kos. But visually, it looks nothing like them. It looks like a Cyclades island.
Whitewashed houses climbing up a hill, windmills at the top, a medieval castle watching over everything. The kind of image you picture when someone says “Greek island” — except almost nobody has heard of it.
Getting there is part of the adventure. You can fly — the airport is tiny, with only national flights and connections from Athens twice a day. It is so small that they open it when the flight arrives and close it once it takes off.
Alternatively, you can take a ferry. From Athens, budget around nine hours. A bit less from Rhodes, and around four to five hours from Santorini. You can save some time with the fast ferry.
In both cases, the trip is not quick or straightforward. And that is exactly why the island has stayed the way it is. The effort filters out the crowds. And what you find on the other side of that effort is something very hard to find anywhere in Greece anymore.
The Chora
The pastel colours of the Chora — unmistakably Cycladic, completely Astypalea
The first thing that hit me — really hit me — was the Chora.
I have seen a lot of old towns in Greece. A lot. And I say this with full confidence: the Chora of Astypalea is one of the most beautiful I have ever experienced. Possibly the most beautiful.
It sits at the top of the hill, with the Querini Castle right at the summit — a Venetian fortress that has been watching over the island since the 13th century. Below the castle, the houses cascade down the hillside in classic Cycladic white, with blue and coloured doors, tiny alleys, cats everywhere, and views over the sea that stop you mid-step.
What makes it different from Santorini or Mykonos — where you also get white houses and spectacular views — is the silence. There are no tour groups filing through. No velvet ropes. No Instagram crowds blocking the narrow streets. You walk through the Chora of Astypalea and you feel like you discovered it yourself.
The narrow alleys of the Chora reward those who wander without a plan
I remember sitting on the steps near the castle one evening, watching the sun drop behind the windmills. Nobody was selling me anything. Nobody was in a rush. It was just the light, the view, and the feeling that I had found something most people would never find.
The view from the Querini Castle — one of the great viewpoints in the Aegean
That moment is a big part of why I keep going back.
The Beaches
Astypalea has some of the most beautiful beaches in all of Greece — and almost nobody talks about them.
The main one close to the town is Livadi — about five kilometres from the Chora, a relaxed village with accommodation right on the water and restaurants a few steps from the sea. I spent a couple of afternoons there just reading a book. Very quiet, very easy, perfect if you want beach life without the chaos.
The beachfront restaurants at Livadi — fresh fish, local wine, no rush
The beaches that really stayed with me are Paralia Steno — absolutely stunning shallow water, partially organised but mostly free, with a lovely taverna serving genuine local food. Honestly, the perfect day.
And then there is Kaminakia — a small cove you reach on a dirt road. Completely raw, no facilities, no sunbeds. Just rocks, clear water, and the feeling that you are the only person on the island.
The sealed road on Astypalea essentially goes from Livadi in the west to Analipsi in the east — less than ten kilometres. Everything else, all the best beaches and hidden spots, is dirt road. Unsealed, sometimes rough, sometimes uncertain.
The only way to reach Kaminakia — dirt road, scooter, no plan
I rode around the whole island on a little scooter on my first trip and never had a problem. The worst-case scenario is simple — the road becomes too rough, and you turn back. Just make sure you have enough fuel, because stations are only in the old town.
On my last trip, I also tried AstyMove — a sort of electric Uber available on the island. It worked well and was reasonably priced. The only drawback was the waiting time, though the service is reportedly expanding for next summer, which is great.
The bus system, unfortunately, is unreliable. There was a timetable, but buses did not always show up. I would not suggest counting on it.
Where to Stay
Where you stay on Astypalea completely changes your experience — because the three main areas feel almost like different worlds.
Astypalea Old Town — The Chora
The Chora is where you go if you want character. Romantic, full of atmosphere, the castle above you, the view in front of you. Perfect for couples. Not ideal with small children because of the steps and narrow alleys, but as an experience, nothing comes close. My personal favourite of the three.
- 🏨 Gerani — Stylish boutique apartment steps from the castle walls
- 🏨 Karai — Design-led stay with stunning Chora and sea views
Livadi
Livadi is the beach option — relaxed, family-friendly, accommodation right near the water. If you are travelling with older kids and want easy beach access without effort, this is your base.
- 🏨 Allegro — Seafront apartment with direct beach access and lovely views
Analipsi (Maltezana)
Analipsi harbour — local life unchanged by tourism
Analipsi sits on the other side of the island. Quieter, more remote, almost no tourist infrastructure. Perfect if you genuinely want to disconnect. The beach is calm, shallow and safe — great with small children.
- 🏨 Akrotiri — Peaceful waterfront property perfect for complete relaxation
Why I Keep Going Back
So — why do I keep going back?
It is not one thing. It is the combination.
It is the Chora in the evening light. It is the dirt road to Kaminakia with the engine switched off and the only sound being the water. It is the fact that in a country where even the remote islands are now on TikTok, Astypalea somehow still feels undiscovered.
And there is something else. Astypalea has this strange geographical shape — two landmasses connected by a narrow strip of land, almost like a butterfly. That shape means that wherever you are on the island, you will be close to a beach.
I first went there when the internet was barely a thing. I have been back several times since. And every time, I find something I missed the last time.
That is very rare. And that is why Astypalea is, for me, the Greek island that surprised me the most.
One more thing — once there, book your boat trip to Kounoupa Island, where you will experience one of the most beautiful double beaches in Greece, shared with just a handful of people. That was definitely one of the highlights of my last trip.
Ready to Visit Astypalea?
If you are planning a trip to Greece and looking for something different — something that still feels genuine, still feels off the map — put Astypalea on your list. Seriously.
If you have been to Astypalea, or if this article makes you want to go — I would genuinely love to know. Drop a comment below. These are the conversations I enjoy most.
