Astypalea Town: The Unknown Crown Jewel of the Aegean Sea

In this destination trip report, we will guide you around the sights of Astypalea Town and show you the best cafés, shops and restaurants.

Astypalea Town

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.

astypalea town
Astypalaia Town (Hora) with its hilltop castle (Kastro) can be seen from far away. ©Paliparan

Astypalea views

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.

astypalea town
The steps next to my studio has some gorgeous bougainvillea. ©Paliparan
astypalea town
You can clearly spot the castle and windmills of Astypalea Town when looking at the island capital from the other side of the small harbour of Pera Gialos. ©Paliparan
pera gialos
View over Astypalaia Town and its fishing port of Pera Gialos. ©Paliparan
astypalaia town
View over Hora and the hilltop Kastro from the southern access road. ©Paliparan
astypalea town
Astypalea Town. On the left you can see a Greek Navy vessel guarding the entrance to the small port of Pera Gialos. ©Paliparan

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.

astypalea windmills
The windmills of Astypalea Town. ©Paliparan
astypalaia windmills
The windmills of Astypalea Town. ©Paliparan
hora astypalaia
The windmills form the entrance point to the old town (Hora) – which is only accessible to pedestrians. There are many authentic taverns found here, which are especially lively in the evening after sunset. ©Paliparan

Climbing up

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.

astypalaia town
Walking through the deserted late afternoon streets of Hora. ©Paliparan
greek cat
It being Greece, there are of course always cats around. ©Paliparan
astypalea cats
Cats on the streets of Astypalea Town. ©Paliparan
astypalea town
If you want to visit Astypalea Town, you better prepare for the many steps and steep streets up the hill. ©Paliparan
astypalea town
Climbing up through the small alleys of town. ©Paliparan
cats of greece
Just like the human population, many Greek cats use the afternoon hours for a little siesta. ©Paliparan
astypalea town
A small alley in Astypalea Town. ©Paliparan
cat greece
Another cute Greek cat. ©Paliparan

Cycladic feel

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.

astypalaia town
Walking through Astypalaia Town. ©Paliparan
town square
A lovely small square in the middle of Hora. ©Paliparan
astypalea town
It is just absolutely delightful to explore the winding lanes of Astypalea Town. ©Paliparan
astypalea town
Bougainvillea and other flowers abound in Astypalea Town. ©Paliparan
astypalea town
In most parts, Astypalea Town has a strong Cycladic feel to it despite being officially part of the Dodecanese (in fairness though, it is the most western island of the archipelago and thus closest to the Cyclades). ©Paliparan
hora astypalea
A street in Astypalea Town. ©Paliparan
astypalaia town
As you climb higher, there are lovely vistas back down towards the sea. ©Paliparan
astypalea town
Just look at this pretty view! ©Paliparan
astypalea greece
Another postcard-perfect Greek view. ©Paliparan

Abandoned buildings

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.

astypalaia town
If you climb up higher towards the Kastro, you will notice a big number of abandoned or decayed buildings. ©Paliparan
astypalaia town
Walking through the streets of town. ©Paliparan
kastro astypalea
The ruins of the Kastro can be clearly seen towering above the old town. ©Paliparan
sea view astypalaia
The higher you get, the better sea views you have. ©Paliparan
astypalea town
Panorama view over Astypalea Town and the Aegean Sea. ©Paliparan
astypalea town
Astypalea Town. ©Paliparan
koen astypalea
The obligatory selfie! ©Paliparan
cats of greece
Cute cat in the streets of Hora. ©Paliparan
astypalea bougainvillea
Picturesque street in the upper part of Astypalea Town. ©Paliparan
astypalea town
Astypalea Town. ©Paliparan
bougainvillea leaves
Pink bougainvillea leaves on the street. ©Paliparan
hora astypalea
Some more pretty bougainvillea in the upper part of Hora. ©Paliparan
hora decay astypalea town
Decayed buildings in the upper part of Hora. ©Paliparan
astypalea kastro
Looking down some steps after climbing almost all the way up to the Kastro. ©Paliparan

Kastro

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.

kastro astypalea
The hilltop Kastro can be seen from almost anywhere in the old town. ©Paliparan
kastro astypalaia
A narrow entrance leads into the Kastro. ©Paliparan
castle couryard
The narrow tunnel opens up to the castle courtyard. ©Paliparan
church kastro astypalea
The entrance to the Kastro basically runs right through the Church of the Virgin of the Castle. ©Paliparan
kastro astypalaia
Most of the Kastro is in ruins after it was hit by a devastating earthquake in 1953. ©Paliparan
agios georgios astypalea
The Church of Agios Georgios is the second church within the castle walls. ©Paliparan
kastro ruins
A ruined house in the Kastro. ©Paliparan
astypalea town
At the time I entered the Kastro, the sun was slowly setting over Astypalea Town. ©Paliparan
pera gialos astypalea
Looking down over Astypalea Town and the adjacent fishing port of Pera Gialos. ©Paliparan
kastro view astypalea town
The views from the Kastro are absolutely gorgeous. ©Paliparan
astypalea coast
Looking out over the barren landscape of Astypalea. ©Paliparan
rooftop bars astypalea
Looking down over some rooftop bars in Astypalea Town. ©Paliparan
agios giorgios church astypalea
The blue dome of the Agios Giorgios Church. ©Paliparan
greek navy frigate
A frigate of the Hellenic Navy guarding the coastal waters of Astypalea. ©Paliparan
astypalea town
Looking down from the castle walls over the Church of Holy Panagia Portaitissa. ©Paliparan

Church

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.

astypalaia hora
Walking down from the Kastro towards the Church of Holy Panagia Portaitissa. ©Paliparan
hora astypalea
Some more lovely bougainvillea in the upper part of Hora. ©Paliparan
Church of Holy Panagia Portaitissa
Church of Holy Panagia Portaitissa. ©Paliparan
Church of Holy Panagia Portaitissa
Church of Holy Panagia Portaitissa as seen from the Kastro. ©Paliparan
church porch
The church porch has great views over the sea. ©Paliparan
church cemetery greece
A small cemetery next to the church. Not a bad location for a last resting place! ©Paliparan
astypalea street
A street next to the Church of Holy Panagia Portaitissa. ©Paliparan
greece cat
Cute cat jumping on the wall to have a look what’s going on. ©Paliparan

Walking down

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!

astypalea sun
As the sun was slowly setting in the evening, it was time to head downhill again and find a place for dinner. ©Paliparan
aegean sea view
Looking out over the Aegean Sea from one of the eastern cliffside road in Hora. ©Paliparan
astypalea view
Looking down over the small fishing port. ©Paliparan
astypalea town
Walking down towards the entrance of the old town. ©Paliparan
hora astypalaia
The cute streets and steps of Hora. ©Paliparan
cats of greece
Cute Greek street cats vying for attention. ©Paliparan
cat astypalaia
Another sweet street cat enjoying life in town. ©Paliparan
cat astypalea
Local cat watching over town. ©Paliparan
old town astypalaia
The maze-like streets of Hora. ©Paliparan
astypalea town
Which way to go? ©Paliparan
astypalea town
The final stretch downhill. ©Paliparan
vintage motorbike
Vintage motorbike parked in the street. ©Paliparan
old town astypalea
Walking back to the entrance of the old town. ©Paliparan
astypalea dimarcheio
The dimarcheio (town hall) of Astypalea. ©Paliparan
keranthos astypalaia
The unbelievably cute shop ‘Keranthos’, which sells excellent quality local sweets and other souvenirs. ©Paliparan

Food

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.

astypalea sunset
When I arrived at the entrance of the old town at sunset, the streets already started to become noticeably more lively. ©Paliparan
windmills astypalea
The sun setting behind the hills near the old town windmills. ©Paliparan
ageri astypalaia
My meal at Ageri was certainly tasty! ©Paliparan
windmills astypalea
The windmills of Astypalea Town are beautifully illuminated at night. ©Paliparan
astypalea night
Both the windmills and the hilltop Kastro are illuminated at night. ©Paliparan

Walking back

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.

bougainvillea night
Walking back to my studio. ©Paliparan
astypalaia greece
View over the old town of Astypalea at night. ©Paliparan
astypalaia night
Astypalaia at night. ©Paliparan

Skala

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.

skala astypalea
Pera Gialos, also known as Skala, is basically the lower half of Astypalea Town on the waterfront. ©Paliparan
hora skala astypalaia
From Hora, it is a steep climb down to Skala on the waterfront, involving many steps. ©Paliparan
skala pera gialos astypalea town
The Skala waterfront is certainly pretty too and has a whole different vibe compared to the winding streets of Hora. ©Paliparan
astypalaia skala
The views over the Kastro of Astypalea Town are excellent from the Skala waterfront. ©Paliparan
skala astypalaia
Skala has several taverns, cafés, shops and other services. ©Paliparan
astypalea town cats
Community cats waiting in front of a local grocery store in Skala. ©Paliparan

Seafood taverns

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.

skala astypalea town beach
The beach at Skala might not be the best on the island, but it does have superb views over Astypalea Town. ©Paliparan
skala restaurant octopus
An enjoyable seafood meal at one of the waterfront restaurants in Skala. ©Paliparan
astypalea sunset
Some gorgeous sunset colours over the entrance of the harbour. ©Paliparan
astypalea town
Astypalea Town at dusk. ©Paliparan
astypalaia town
Astypalea Town at dusk. ©Paliparan
astypalea
Another gorgeous night time view over Astypalea. ©Paliparan

Day three

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!

astypalea town
Admiring the beauty of Astypalea Town for the final time this trip. ©Paliparan
astypalea island
I absolutely adored Astypalea Town and couldn’t get enough of the fantastic views. ©Paliparan
hora astypalea
One final walk through the streets of Hora. ©Paliparan
astypalea view
Final picture of Astypalea Town before I drove to the ferry. I really hope to revisit this fantastic island one day! ©Paliparan

Conclusion

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
14. Review: Traditional Apartments Alexandra, Kastellorizo, Greece
15. Kastellorizo: A Look Around Greece’s Easternmost Island
16. Hiking on Kastellorizo: Two Sunset Hikes Detailed
17. Review: Olympic Air Kastellorizo to Rhodes (Dash 8-100)
18. Guide: How to Travel From Rhodes to Halki by Ferry
19. Review: Dorothea Apartments, Halki, Greece
20. Halki Town: Eating, Swimming & Relaxing in Beautiful Emborios
21. A Hike to Horio: Exploring Halki’s Old Abandoned Capital
22. Guide: The Best Beaches on the Island of Halki

** rest of the chapters to follow soon **

Koen

Koen works as a freelance journalist covering south-eastern Europe and is the founding father and editor-in-chief of Paliparan. As a contributor to some major Fleet Street newspapers and some lesser known publications in the Balkans, he travels thousands of miles each year for work as well as on his personal holidays. Whether it is horse riding in Kyrgyzstan’s Tian Shan mountains, exploring the backstreets of Bogotá, or sipping a glass of moschofilero in a Greek beachside taverna, Koen loves to immerse himself into the local culture, explore new places and eat and drink himself around the world.

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.