Since starting this website, I’ve documented my Greece trips with (mostly) daily blog posts. You can find them linked at the top of the page under the Trip Reports menu heading, but I’ll describe them here, too:
- 2017 Cyclades Tour: Andros, Tinos, Mykonos, Naxos, Paros, Ios, Santorini & Crete
This was my first island-hopping experience back in 2017. I managed to fit a lot of islands into 18 days – too many, really – but the first three (Andros, Tinos and Mykonos) were with my friend Ed, who only had a few days available to travel, so we crammed them together and were only on Tinos and Mykonos for one night each.
- Mini Cyclades 2018: Mykonos (including Delos), Naxos (twice) and Koufonissi
In 2018, I had another opportunity to visit Greece with my friend Ed, though again, he would only be around for the first four days while I continued on my own for a further week. Flying directly to Mykonos from the UK allowed us to jump straight into the Cyclades. From there, we visited Naxos; then, after Ed’s departure, I continued to Koufonissi.
A slight lack of planning saw me return to Naxos for a few more nights before taking the ferry to Mykonos for my flight home. It was a good trip, but in hindsight, I should have found an alternative to Naxos for the final few days – Paros would have worked.
- Amorgos 2019: Mykonos, Naxos and Amorgos
Whether this trip counts as ‘island-hopping’ depends on your definition: we never stayed overnight anywhere other than Amorgos! We flew into Mykonos again for convenience and had to stop a few hours on Naxos to make our connecting ferry to Amorgos, so we technically set foot on three different islands!
It was my shortest trip, but Ed was with me the whole time, which made a nice change. We spent three nights in Aegiali and two in Katapola and really enjoyed exploring Amorgos. The trip was also earlier in the year than I usually travel to Greece, setting off at the very end of May 2019. As a result, the island was pretty quiet, and the sunny weather wasn’t as hot as I expected, but it made for ideal hiking conditions.
- Cyclades 2019: Santorini, Folegandros, Naxos and Mykonos
If you haven’t noticed, I am slightly fascinated with the Cyclades! Plus, it’s so easy to island-hop there that I couldn’t resist returning just a few weeks after returning from Amorgos. This time, instead of Ed, my girlfriend came with me, so there was a bit less focus on hiking and more on relaxation!
We flew into Santorini for three nights, which I enjoyed a lot more than my first visit in 2017 – having company helped – then onto a new island, Folegandros, for a further three nights. We both enjoyed it there: lovely accommodation and some great food. We spent six nights on Naxos for the last leg, which was its usual excellent self. Unfortunately, the trip ended on a bit of a sour note as we got stuck overnight on Mykonos when our flight back to the UK was delayed due to bad weather over Gatwick.
- Western Cyclades 2020: Milos, Sifnos, Serifos, Syros and Andros
Despite travel restrictions due to the COVID-19 pandemic, I was lucky to fit a 16-day trip to Greece in early September 2020. It was another Cycladic adventure, but, except for Andros, all islands I’d never visited before.
I flew into Athens and took my first internal Greek flight, landing on Milos after realising it was much easier and faster than the ferry from Piraeus. I then hopped to Sifnos – now my favourite Greek island – before visiting Serifos and Syros. I did all this alone, then met Ed on Andros for the last few days.
- Greek Odyssey 2021: Crete, Karpathos, Rhodes, Tilos, Kos, Amorgos, Naxos, Ios, Sikinos and Sifnos
After several years of practice island-hopping with various short and medium-length trips described above, I finally decided to quit my full-time job and spend an extended time travelling around Greece. This turned out to be a 73-day odyssey starting on Crete, passing through the Dodecanese and – of course – into the Cyclades again. Though I revisited several islands from previous trips, I also saw a lot of new places: Karpathos, Tilos, Kos and Sikinos, plus parts of Crete that I’d never been to before.
It was a fantastic experience, so I planned and executed an even longer trip in 2022…
- Greek Odyssey 2022: Mainland Greece (Peloponnese), Paros, Astypalea, Kos, Amorgos, Ios, Crete, Aegina, Agistri, Athens and Sifnos (yes, again!)
Although aspects of the trip were similar to the previous year, with return visits to Kos, Amorgos, Ios and Sifnos, it also featured several new and exciting elements: my first time in mainland Greece exploring some of the Peloponnese (Kalamata, Mystras, Mount Taygetus, Monemvasia and Elafonisos); three new islands with Astypalea, Aegina and Agistri, plus I finally managed to visit Athens and explore the iconic city centre.
Finishing the journey on Sifnos once again proved to be a great end to the trip, especially as my girlfriend had flown out to Athens and was visiting my favourite island for the first time.
