In this destination trip report, we will guide you around the sights of Astypalea Town and show you the best cafés, shops and restaurants.
Arguably the greatest highlight of the island of Astypalea (also spelled as Astypalaia, or Αστυπάλαια in Greek) is the island’s capital, simply called Astypalea Town or Hora by the Greeks.
Although it doesn’t have the same allure as more famous places in the Aegean such as Oia on Santorini or Mykonos Town, Astypalea Town is certainly not inferior to those places. In fact, the relative obscurity among foreign holidaymakers means that you can enjoy the sights and sounds without being drowned out by giant tourist mobs.
Astypalea Town has always been relatively popular among Greek holidaymakers as well as a handful of foreign travellers in the know, which means that the island capital has retained much of its original character unlike some on the islands more saturated by tourism.
Having settled down in my lovely boutique studio just outside of Astypalea Town, it was time to walk the short distance to the entrance of the old town.
If you are looking for some fabulous views over the island capital, you can simply walk or drive along the northern and southern access roads as both have sweeping views over the hilltop town.
Basically, Astypalea Town exists of the old town proper (Hora/Chora) with its hilltop castle (Kastro) and its harbour at the foot the hill which is called Pera Gialos.
It must be one of the most stunningly located towns in all of Greece and the view doesn’t grow old even if you stay a week.
Entering the old town
The old town of Hora is completely car-free so if you arrive in town with a rental you have to park it at the town’s entrance. There is a small (free) parking lot, although this fills up pretty quickly, especially during evenings when both locals and tourists flock to town for dinner and drinks.
You thus might have to drive a bit away through some nearby streets and find any suitable parking place along the road.
The pedestrian area begins at Astypalea Town’s famous windmills, one of them having its blades still attached. Here you will find also some of the most popular restaurants of town, which at lunchtime are rather empty but are bustling with customers later in the evening.
Immediately after the entrance to the old town, there are several streets climbing steeply up to the hill. On my first day on the island, I visited Astypalea Town in the late afternoon, a time of the day when such towns are eerily quiet.
There were almost no humans to be seen on the streets except for the occasional other tourist and the omnipresent Greek community cats.
Although the streets are much more lively in the evening which makes for an excellent time to visit as well, I prefer walking around in the late afternoon as it’s just so much better for photography purposes, especially given that the whitewashed houses bask in the gorgeous lights of the slowly setting sun at this time of the day.
Astypalea is part of the Dodecanese archipelago, but the streets and whitewashed houses definitely have more of the feel of a town on one of the islands of the Cyclades.
The white steps with their grey decorations painted on them also have more in common with Cycladic cities such as Naxos Town. The same can certainly be said too about the doors and window frames painted in light blue.
One of the great aspects of Astypalea Town are the partial sea views you have from many of the streets leading down the hill as you climb higher up. This creates some fabulous vistas, especially so on the streets with overhanging bougainvillea and other flowers.
At every street corner, you have the sudden urge to stop again to take in the view and make some more snaps. After just walking in town for half an hour I had already snapped well over a hundred pictures as the town is just that gorgeous.
As you climb up higher towards the Kastro, you will start to notice that more and more of the buildings are either abandoned or in a slight state of neglect and decay compared to the perfectly plastered buildings lower on the hill.
It brings up an entirely different vibe to the town – although I certainly cannot say it is any less beautiful.
From almost everywhere in town, as well as in the wider surroundings, you can see the hilltop castle (kastro) of Astypalea Town. Originally, the main settlement on the island was down at the water level, but due to the danger of marauding pirates the local inhabitants gradually moved their houses higher up the hill.
When Astypalea was occupied by the Venetians in the 14th Century, a rich Venetian noble family decided to build the hilltop castle to protect the town.
It would end up standing fierce and proud above town until its eventual decline after the Venetians were first replaced by the Ottoman Turks and when Astypalea finally became part of the modern Greek state.
In the middle of the 20th Century, the last inhabitants moved out of the Kastro after a devastating earthquake crippled the last stone houses. You can still see the impressive ruins of these structures inside the Kastro.
You enter the castle through a narrow entrance, which opens up towards the main courtyard. If you look back, you can see that the tunnel-like entrance actually runs right underneath the blue-domed Church of the Virgin of the Castle.
There is another church within the premises of the castle walls. This is the smaller Church of Agios Georgios, from where you have commanding views over the deep blue waters of the Aegean Sea.
Although there isn’t much else to see within the Kastro, the sweeping vistas from the other side of the castle over Astypalea Town and the little harbour of Pera Gialos are excellent.
Astypalea Town has one other church which is well-worth a visit. This is the Church of Holy Panagia Portaitissa, located just outside the Kastro walls on the southern tip of Hora.
Unfortunately, the church itself was closed at the time I arrived, but the small church garden and surrounding streets make for a pleasant walk.
As the sun was nearly setting, it was time to walk back down from the Kastro through the winding lanes of Hora. Since I had pretty much skipped lunch, I was getting quite hungry and eager to test out one of the restaurants near the windmills.
Needless to say, there were plenty more great views to admire walking down the hill.
A must-stop on your way down is the little store called ‘Keranthos’, which you will find at the entrance of the old town. This gem of a shop sells all kind of local, organic products such as pastries, herbs, liqueurs, jams and other preserved foods. I can highly recommend the fig compote, among many other products!
There are plenty of good restaurants to be found in Astypalea Town, with the bulk of them being located near the windmills at the entrance to the old town.
Maria, the kind host of my studio, had recommended the local tavern ‘Ageri’ to me. This turned out to be a great choice, as I certainly enjoyed my meal.
Given that I was extremely hungry, I ordered some dakos (Cretan salad of tomato, wild greens, peppers, tomatoes and feta and barley rusk) as well as some grilled cheese and some pork dish in a clay pot. All of it was absolutely tasty.
Although the taverns were still fairly empty when I set down, they quickly began to fill up with both locals and tourists after darkness fell. Ageri indeed seemed to be very popular among the locals and Greek tourists, as some people even began to wait on the square near the windmills until some tables became available!
The square also seemed to be a highly popular place for the local kids to run around and play on now that the temperatures had finally dropped to a more pleasant level.
After the excellent meal, I retreated back to my studio being tired from the long day with the knowledge that a good bottle of Greek red wine was awaiting me.
There were some excellent views over an illuminated Astypalea Town from both the winding coastal road, as well as from the terrace of my studio. Dare I say it, I think that the view over town is even prettier at night than during the day, or at the very least more evocative with the hilltop kastro shining bright in the darkness as a beacon of light.
Although there are plenty of great accommodation options smack in the middle of Hora, I certainly did not regret opting for a studio just outside the old town as it had the benefit of having an excellent view.
The next day I picked up my rental car and went on to explore a huge chunk of Astypalea and to visit some of the island’s best beaches, something which I will detail in depth in the next chapter.
Having returned from my drive in the late afternoon, there was one important part of Astypalea Town left which I didn’t manage to discover yet: the small fishing harbour of Pera Gialos, which is often simply called Skala by the locals.
Until recently, Skala was also the main port of the island of Astypalea, although nowadays all ferries use the small port of Agios Andreas, located in the middle of nowhere some 7 kilometres away by road.
This means that Skala is nowadays essentially a fishing village, even though it feels like just another neighbourhood of Astypalea Town being fully intertwined. As the entire hill is built up all the way from Skala down at the sea to the hilltop Kastro, you don’t really see the distinction between Skala and Hora when looking from afar.
From the entrance of Hora – or anywhere along the main coastal road higher up on the mountain – it is a steep climb down to Skala by road or steps.
Once you hit the waterfront, you will find plenty of local taverns, shops and services. In fact, most of the shops and services of Astypalea Town, such as the local banks, are located here and not in Hora!
At the far end of Skala, at the intersection with the main coastal road, you will also find the island’s biggest supermarket (Kritikos), which is a handy place to stock up on supplies if you stay in a self-catering apartment or studio.
Although Skala does have a stone beach, it doesn’t rank among the best beaches on the island of Astypalea in my opinion, although it would certainly do for a quick dip if you don’t have a rental car to drive somewhere else.
One thing which the Skala beach does have, is many seaside taverns, some of them even having tables right on the beach of overlooking them. Most of them have superb views as well over Hora and the hilltop Kastro, making them great locations for a seafood meal.
That was exactly what I did for dinner on day two on the island, sitting down at ‘Akrogiali’ for some grilled octopus and a Greek salad.
Although the Skala harbour opens up to the sea on the east and the sun sets on the wrong side behind a hill, the skies still gave away some gorgeous purple and red sunset colours.
After a great meal and a few glasses of white wine, I climbed up the hill again to my studio to end day two on Astypalea.
On day three on Astypalea, I again used the entire day to tour the island with my rental car, only to return to Astypalea Town in the late afternoon to check out of my studio and to pick up my luggage for my overnight ferry to Kastellorizo.
Of course, I had to make one last walk through Hora and to absorb the last views over gorgeous Astypalea Town before driving down to the ferry dock. These views never grow old, really!
I’ve visited many lovely Greek islands, but Astypalea really is a class apart. Although there are plenty of attractive beaches and towns on the island, it is Astypalea Town itself which is the true highlight.
With its picture-perfect vistas, winding lanes, old windmills and hilltop castle, it really is something like a crown jewel of the Aegean Sea. When people think of beautifully located Greek towns they will without doubt mention Santorini, but Astypalea Town is absolutely magical too.
Whether you admire the town from afar during day or night, explore the small alleys, or sit down at one of the great cafés and taverns, there is so much to like about Astypalea Town!
Perhaps the best part of it all is that the place is relatively undiscovered among foreign tourists. Some 90 percent of annual visitors are Greeks from other islands or the mainland, which means that Astypalea still retains its authentic character and off-the-beaten-path atmosphere.
Astypalea Town really is one of Greece’s best island capitals and I cannot recommend a visit enough to this fabulous place.
Trip report index
This article is part of the ‘A Dodecanese Dream: Summer Island Hopping in Greece‘ trip report, which consists of the following chapters:
1. Back in the Skies – My First International Flight in the Age of Corona
2. Review: Kimon Hotel, Athens, Greece
3. Exploring Plaka: Through the Winding Streets of the Old Town of Athens
4. Climbing up the Acropolis: Visiting Athens’ Most Famous Sight
5. Review: Skyserv Melina Merkouri Lounge Athens Airport
6. Review: Sky Express Athens to Naxos (ATR 42)
7. Review: Studios Zafiri, Naxos Town, Greece
8. Naxos Town: The Gorgeous Historic Heart of the Cyclades
9. Review: Blue Star Ferries Naxos to Astypalaia
10. Review: Belvedere Studios, Astypalaia Town, Greece
11. Astypalea Town: The Unknown Crown Jewel of the Aegean Sea (current chapter)
12. Astypalea Island Guide: Exploring the Butterfly of the Aegean
13. On a Night Boat in Greece – Astypalea to Kastellorizo With Blue Star Ferries
** rest of the chapters to follow soon **