Sunset over the castle in Chora from the windmills

Located where the Dodecanese meet the Cyclades, Asypalaia is as charming a Greek island as they come. 

Not many tourists venture out this far but that’s all to the good. Even in the peak summer season you’ll have large parts of the island to yourself. Sure, on a hot August day the beaches will be crowded, but they’ll be crowded with friendly Greek locals as opposed to pasty British holidaymakers. And when Santorini feels oppressively crowded, that’s a magical thing.

Honestly, Astypalaia is everything you imagined a Greek island to be; whitewashed houses, cobblestoned alleyways, sun-drenched beaches and a ruined castle at the top of the hill. 

While there’s not an endless list of things to do here, it’s a great place to escape the crowds and spend a few days. Dive straight into this ultimate guide to Astypalaia to help you plan your epic adventure. 


A good time to visit Astypalaia is from late May to October. June to August are best for swimming but are also the busiest, so if you like smaller crowds aim for the shoulder seasons of May or September-October. If you’re planning on travelling in the off season check before you go as ferry services may be reduced. 


Astypalaia is a little harder to get to than some Greek islands, but trust me when I say it’s worth the effort. We made our way there from Naxos by ferry, which took 4 hours and cost €20. You can find ferry routes to Astypalaia here. (Note: ferry times change with the seasons, so make sure to check before you go). Astypalaia also has a small airport and we chose to fly back to Athens rather than catch the 9-hour ferry. Flights to Astypalaia run only from Athens, and operate only during summer. 

Greek church in . Astypalaia Harbour

Castle of Guerini

There’s not many must-see tourist attractions on Astypalaia, and honestly, that’s part of the appeal. If you can drag yourself away from the ocean for a spot of site-seeing, head up the hill to the castle of Guerini. An impressive castle founded in 1413, today it lies almost completely in ruins. The blue-domed churches stand out against the rubble, and the view out over the ocean is spectacular. 

Entrance to the Castle of Guerini is free. 

Blue domed church surrounded by rubble in Astypalaia

Chora & the Traditional Windmills 

Of all the Chora’s I visited in Greece, Astypalaia’s Chora was my favourite. Gleaming whitewashed walls, the sea peeking out from behind buildings… Chora is a dream. 

Make your way up the hill to Chora and you’ll stumble across a row of traditional windmills. Once used by the people of Astypalaia to mill grain, today the 8 windmills make for a great photo opportunity. 

Row of windmills in Chora, Astypalaia

Dinner at Αγονη Γραμμη

You know that meme about thinking about the chocolate cake you had on holiday in Spain when you were 11? It’s not chocolate cake I dream of (though I love chocolate cake); its pasta. 

Specifically, a simple Greek pasta I had at Αγονη Γραμμη. You hardly expect Astypalaia to be where you’ll find the pasta of your dreams. It’s a small island, and there’s not the amount of restaurants you’d find on Santorini or Mykonos. I hadn’t done any research on where to eat, and so my Dream Pasta came as a complete surprise. Perfectly cooked, simple yet tasty, this pasta was So. Damn. Good. 10/10 would go back to Astypalaia just for the pasta. 

Be a beach bum and explore the island’s beaches

Getting around Astypalaia requires a car, scooter, or a little planning. If you’re not comfortable riding a scooter over the unsealed roads and your budget doesn’t extend to hiring a car, you can use the island’s buses to get around.

To get to Plakes Beach catch the local bus from the harbour (opposite Safran Restaurant). From the bus stop at Plakes it’s a 10 minute walk down to the beach. Plakes Beach is stunning. Ok, the pebbly ground isn’t the most comfortable to sunbathe on, but the turquoise water against the brown hills is incredibly picturesque. There’s no shops near Plakes Beach so make sure to bring water, sunblock, and snacks. Beach snacks are compulsory.

If you fancy a day of beach hopping it’s easy to hop back on the bus and head to Maltezana Beach. Maltezana Beach is equally as pretty as Plakes but features white sand and a small selection of restaurants nearby. 

Closer to Chora, Livadi Beach is one of the most popular on the island. If you have your own transport consider venturing out to Vathi Beach or Psili Ammos. Astypalaia has a range of lovely beaches, and it would be amiss of you not to explore some of them. 

A boat is tied to the end of the pier, Astypalaia
Man heads down to Plakes Beach, Astypalaia

Relax in the Harbour 

Though it’s not the prettiest beach in the world you could easily spend an afternoon at Astypalaia’s harbour beach. The water is remarkably clear, and the beach is located near numerous cafes and restaurants. Spend a couple of hours reading, swimming, and enjoying the view of whitewashed buildings and Chora perched high on the hill. 

Time your visit with lunch and call in at Ouzeri Anastasia. Run by a lovely Greek couple, this charming ouzeri offers tasty food in a great setting. 

Whitewashed buildings of Astypalaia's Harbour

Cocktails at Castro Bar

Would your Greek island experience be complete without a cocktail or two? For the best sunset spot in Astypalaia (and a killer Passion Mango Mojito) head up to Castro Bar

If you’ve followed this blog for a little while, you’ll know I love seeking out bars with a view. Rooftop bars, bars with views of castles, trendy bars with sweeping ocean views… I have to say, finding great bars is a talent of mine. Of all the bars I’ve been to throughout my travels Castro Bar would for sure be in the top 5. 

Sunset from the Castro Bar, Astypalaia

Other things to do on Astypalaia:

I didn’t go, but if you’re into history or just the macabre, the Infant Cemetery of Astypalaia sounds like a fascinating site. The archaeological site contains over 2000 jar burials belonging to babies or toddlers, and it’s believed to be the only infant cemetery in the world and an important shrine to infertility. 

Want to learn more about Astypalaia’s history? Check out the Archaeological Museum, a small museum containing artefacts from the prehistoric period to medieval times, including ancient jewellery, stone tools and pottery. 

Stay: We stayed in Aphrodite Studios and it was one of the most idyllic hotels of our stay. At €310 for a 3-night stay (€51.67 each per night) it was a bit of a splurge on our backpacker’s budget, but the room was lovely. If you’re not too restricted by budget, I’d totally recommend staying here. 

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The Ultimate Greek Island Guide: Astypalaia Edition
The Ultimate Greek Island Guide: Astypalaia Edition

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