A Dodecanese Dream: Summer Island Hopping in Greece

In this trip report, we will go island hopping in Greece and visit Astypalaia, Kastellorizo, Halki and Rhodes in the Dodecanese as well as Naxos in the Cyclades.

A corona respite

After a couple of months of lockdown in spring due to the COVID-19 virus pandemic I was badly in need of a proper holiday. With many countries – especially those outside of Europe – being firmly out of bounds, I decided to choose a destination close to home.

Spending the summer in Greece seemed to be a natural choice as the Hellenic Republic had relatively loose entry restrictions and local corona measures.

Having lived in Greece before, I have developed a soft spot over the years for the country, its people, food and culture to the extent that you can call me a Hellenophile of some sorts.

Even though in normal years I would actually avoid spending the high summer months of July and August in Greece due to the massive influx of holidaymakers and my dislike of big tourist crowds, I knew that this year would be the odd year out.

Travel planning

Although I played a bit with the thought of visiting the most famous of Greek islands such as Santorini during this trip, I eventually decided against it knowing very well that even with dwindled crowds I would still prefer the more authentic islands off the beaten track.

For some weird reason I always wanted to visit Kastellorizo, Greece’s most remote island located far away to the east. When looking at ferry schedules through the excellent ferry booking tool of Viva, I found an awesome overnight connection from Astypalaia to Kastellorizo which worked out great schedule-wise.

As Astypalaia was another island I always wanted to visit, I had the central part of my itinerary now fixed.

kastellorizo greece
Hiking on the gorgeous island of Kastellorizo. ©Paliparan

Flights and ferries

What was left remaining was the issue how to get to Astypalaia, and what to visit after Kastellorizo. As I had around two weeks of holiday, I could still add some other islands to my itinerary as well.

From Kastellorizo, it made the most sense to go to Rhodes given that it’s the only island with a frequent connection by ferry or plane. I decided to combine a visit to Rhodes with a stay on the nearby island of Halki, which looked cool on pictures and seemed quiet enough despite its proximity to its package tour and charter airline-infested neighbour.

Unfortunately, the Athens to Astypalaia Sky Express flights were only bi-weekly and didn’t really match my schedule. With the ferry from Piraeus (the port city in the greater Athens area) to Astypalaia not having the best schedule either, I therefore decided to fly from Athens to Naxos.

It allowed me to spend some time in Naxos Town, before catching a ferry to Astypalaia the following day, optimising time spent on the ground instead of on a ferry.

Final route

My final itinerary would start in Bucharest with an Aegean flight to Athens, followed by a Sky Express flight to Naxos. From there I would take a Blue Star Ferries ship to Astypalaia, from where I would hop on another Blue Star Ferries boat to Kastellorizo.

From Kastellorizo I would fly to Rhodes with Olympic Air and immediately hop on a local ferry (Nissos Halki – Velis Line) from the port of Kamiros Skala to Halki. Returning to Rhodes by the same ferry, I would then fly back to Athens with Olympic Air and back to Bucharest with Aegaen.

In the end, the route of my summer trip to Greece would therefore look like this:

dodecanese dream map
On this trip, I will take five flights in total. The ferry trips I will detail in each individual chapter of this trip report. ©Great Circle Mapper


In this ‘A Dodecanese Dream: Summer Island Hopping in Greece’ trip report, you can expect the following highlights:

– Reviews of Greek domestic flights on Olympic Air and Sky Express
– Some wonderful boutique hotels and apartments
– Exploring all around gorgeous Astypalaia and its magical island capital
– Winding down on the remote island of Kastellorizo with its picture-perfect harbour
– Swimming and hiking on the low-key island of Halki
– A lot of delicious Greek taverna food

Spoiler alert: Although the whole summer Greece seemed to be like normal despite the ongoing corona crisis, it would certainly be an experience unlike others given the absolutely huge drop in tourist numbers. It really felt like a dream, having some of Greece’s most fantastic spots almost exclusively to myself!

astypalaia greece
View over the old town of Astypalaia. ©Paliparan
kastellorizo dodecanese
Remote Kastellorizo is Greece’s easternmost island. ©Paliparan
seafood greece chalki
A seafood dinner on the island of Halki. ©Paliparan

Trip report index

This trip report 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
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

** rest of the chapters to follow soon **


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.

2 thoughts on “A Dodecanese Dream: Summer Island Hopping in Greece

  • November 19, 2020 at 10:09 pm

    Ah, Koen, you’re bringing back memories of my mis-spent 1980s youth! I spent much of September from 1982-1990 island hopping in times where it was much quieter than now and many of the islands did not have a runway where an A320 could land and it was all so much nicer back then. The south of Rhodes was one of my favourite places and I might just try and go back there next year.

    • November 20, 2020 at 7:29 pm

      Misspent? Seems like an amazing way to spend the days! I always try to visit Greece twice a year at least, once in Spring (I love the wildflowers) and once in (early) autumn. With corona putting a hold to many plans, I had the feeling I needed to make one major Greek trip this year, with this the result! (and it was lovely).

      You are right that with the advance of mass tourism a lot has changed, although many islands (or parts of some islands) are still relatively unspoilt. I cannot comment much on Rhodes as I never ventured away from Rodos Town and Lindos, but there are definitely still some authentic, great places on big islands like Crete or those islands which do not have easy ferry connections and lots of international flights (Karpathos, to name another island I love). Curious what you think of southern Rhodes if you manage to get there again!


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