Go Greek Island Hopping was number eight on my 50-before-50 list. Although I went to Greece with the intention of doing this in 2020, I officially crossed it off the list in 2021. You could say that this adventure changed my life. In a twist of events, I ended up moving to Greece and gaining residency. Visiting every Greek Island became a whole bucket list of its own and led me to start a Greece travel site.
So here’s the story of how I finally crossed Greek Island Hopping off my list.
In October 2020, I had just over two weeks between housesits with nowhere to live. Covid restrictions had just started being really changeable again so housesits were a bit tentative. Instead of booking one and then having it cancelled on me at the last minute, I decided to go to Greece.
Greek Island Hopping, Take One
How long do you need for Greek island hopping? Well, I thought 14+ days was a good amount of time to see a few different islands. And to begin with, I did what lots of people do and tried to make a schedule crammed with loads of different islands. But, when I started looking at the logistics, I could see it wasn’t going to work. Andros (where I ended up doing item number 37 in November 2021) was the first place I wanted to go. Unfortunately, the ferry schedule from there to the rest of the islands on my list was getting a bit sparse by mid-October. So that one had to go.
Then I reminded myself that I wouldn’t actually be on holiday. I still had client work to get done including for a client who was going to be in launch mode. That meant it would be better for me to be in one place for longer. Travelling can take up a lot of time and brainpower so, in the end, I went to Naxos for most of the two weeks. I hopped over to Paros for the last few days.
I returned to the UK for my last booked housesit and then had nothing confirmed after that. Before I even touched down in the UK I knew I would be heading back to Greece. I didn’t feel like I could cross this off the list just yet because in the end, I’d spent most of my time working. And although I’d had a beautiful sunset view, enjoyed some lovely walks and got to swim in the sea, the experience wasn’t quite what I’d had in mind.
Greek Island Hopping, Take Two
I returned to Naxos at the end of October 2020. Only a couple of weeks later we went into lockdown for about 6 months. That meant there was a complete travel ban. We couldn’t even drive around the island to a nice walking spot for exercise, never mind travel to other islands. But I got on with life on the island. I moved somewhere lovely, spent time looking after stray cats and volunteered at the dog shelter and my freelance clients kept me busy with work too.
The only place I got to go was Syros. I had to get special permission from the police to go and do my residency application. It was a bit daunting but all good in the end. Finally, after an interesting winter, we were able to travel again.
Island One, Naxos
On the 15th May 2021, tourists were allowed back into Greece and it was all systems go. I moved out of my winter accommodation to make way for the tourists. It’s very common, particularly on the islands, for housing to be seasonal.
So the cats and I moved somewhere else on the island for a month and because all movement restrictions were lifted I was finally able to explore Naxos properly. I went to see the stone kouroi statues, huge marble statues that had been abandoned at ancient quarries. I saw the temple of Demeter close up, instead of just from the hillside on my hikes. The villages transformed in front of my eyes. From closed up ghost towns they became pretty places with street cafes and tourist shops. The museums opened their doors again and the sun shone down from perfect blue skies.
Heading to Tinos Island
I was in a bit of a quandary about where to live when the summer hit. (I’m writing this up in December 2021 and to be honest, I’m still in a bit of a quandary about where to live.) I loved Naxos but I really wanted to go and explore other islands. Ideally, I’d have found a base on Naxos where I could leave the cats and get a housesitter in. But year-round accommodation on the islands is like gold dust and I didn’t manage to find anything.
So we headed off to Tinos since I’d found a decently priced, short-term apartment. I was excited and also a bit nervous to be travelling somewhere new. As I drove up to my accommodation in the north of the island I knew everything was going to be fine. There were more breath-taking views, pretty villages galore and wonderful food to be discovered.
I juggled exploring the island with client work and writing my How to Become a Housesitter course. The weather was red hot and I sweated it out in my AC-free apartment.
I was living in a really small, traditional village that observed quiet hours. There was a busy cafe opposite me that was lively and bustling from the morning until the evening. But at 2pm you could hear a pin drop in the village. It was lovely and quiet for working and then things got going again about 6pm. The location was perfect for several of the hiking trails on the island too. Unfortunately, the weather was not. This is definitely an island I want to revisit at a cooler time of year.
Hopping to Syros
Syros, the administrative capital of the Cyclades, is just a 30-minute hop from Tinos. I went there next as my residency permit was ready. It took a while for Syros to grow on me and my trip there was kind of chaotic. I definitely need to go back and visit again with a fresh slate.
One of my cats escaped on the ferry to Syros just before we docked. Luckily I manage to catch her but my stress levels went through the roof. Especially as it happened a second time in the back streets of Ermoupolis. Turns out the box had a design fault. I was literally herding cats as they ran off in different directions down the street. Hot, exhausted and tearful I finally managed to scramble up an olive tree to catch one of them. And I pulled the other out of a tetanus-infested pile of rusty somethings.
I also had my first not very good Airbnb experience during this trip. I ended up leaving early and for the next few weeks, I felt sick to my stomach any time I heard someone speaking French (The owner was French!) Anyway, I moved to another Airbnb where the owners were so lovely. They gave me fresh bread, or fruit or homemade ice cream every day and I got to explore Hermoupolis a bit more.
Syros is more about city living than beach life. It’s got very beautiful architecture and has a very strong Venetian feel to it. Hermoupolis, the main town, is a bit different to other Cycladic towns. It looks very grand with the mansions and the opera house built in the style of La Scala, Milan. When I was there I remember feeling like I wasn’t on a Greek island anymore. But you have to appreciate it for something different.
Anyway, I got my permit which was the main reason for visiting. I think the wild beaches in the north are more my scene and there are some great restaurants in Hermoupolis that I didn’t get to try out so I will go again.
The next island I visited after Syros was Kea. It’s about 4 hours on the ferry and pretty close to the mainland. By now it was the beginning of August and I got lucky with a cancellation for my accommodation. I wasn’t able to hire a car on this trip as it was peak season and there was nothing left.
Again, Kea is going to be worth another look. It’s well set up for hiking but August isn’t the month to do it. There were quite a lot of wildfires in Greece during that time and we actually received an emergency text during the visit banning us from any kind of woodland area.
But the beaches on Kea were good and I saw the best sunsets since Naxos. I swam from a private beach and ate acorn cookies from the oak trees down the east side of the island. (Well, the cookies didn’t come directly from the oak trees, but you know what I mean!)
I stayed in Kea for just a few days before continuing north to Athens. I had a housesit arranged for a month and I put the cats in the kennels for that time. It was far from ideal but I was stressed about their safety after the ferry debacle. Finding somewhere to permanent to live on the islands in July and August is quite impossible so it seemed like the best option at the time.
The Star of Mykonos
After looking after Oscar parrot for a month, I was on the move again. I headed to Mykonos to see what all the fuss was about. I liked the island more than I expected to, but it’s not a patch on Naxos.
The whitewashed old town is pretty and it was fun to walk through the streets with the designer shops. I have to say, many of the beaches in Mykonos are long, golden stretches like in Naxos. But most of them are taken over by sun loungers and bars and parties. Which is, of course, the main attraction of Mykonos. It’s not my scene but it was fun to go there for a short while and I did enjoy visiting sacred Delos island.
From Mykonos, I had a brief sojourn to Paros for the day to see about a house for the winter. It was a relief to get something agreed upon and know that my cats would be happy with the space.
After I finished my stay in Mykonos I took the popular route down to Santorini to see what she had in store for me. The sunsets in Santorini are truly breathtaking and the scenery of the caldera is stunning.
I enjoyed staying in one of the more traditional villages and then visiting busy Oia and Fira. While I was on Santorini I had a photoshoot for the Daily Mail. I’d already been interviewed by a journalist about my housesitting experience and this was the second part.
Santorini’s quite a big island and there was a lot to get around. I visited Ancient Thira, saw some of the beaches, went shopping in Fira and had a mini photoshoot in Oia. I went to Ammoudi Bay and hopped over to Thirasia and explored that tiny island by e-MBT (electric mountain bike).
After Santorini, I just had enough time to squeeze in a trip to Anafi island before heading back to Athens to collect the cats. Like Thirasia it’s a really small island. It took about 90 minutes to get there and I just stayed overnight. But with the ferry schedule, I had a decent amount of time to explore.
The high point, literally, was walking up the second largest monolith in Europe. (The biggest is Rock of Gibraltar.) There’s a tiny monastery at the top and a phenomenal view. There are quite a few walking trails if you go to visit and some lovely beaches too.
My island hopping adventure was slowing down by this point but my house in Paros wasn’t available until November. So after heading to Athens for 24 hours to collect my cats I moved on to Andros.
I loved Andros and was so glad I finally made it there. The island is beautiful with miles of walking paths. It’s a lush island and similar to Naxos rather than other Cycladic islands in that regard. It also has a feel of Syros in Andros Chora, the main town. The food is good too, and the people are friendly.
I volunteered alongside the Andros Routes and Clean Green Andros projects. Helping clear plastic from the ocean number 37 on my bucket list. I really enjoyed working alongside the others and getting to know the island through them.
My five weeks there went way too fast and it was time to move to Paros.
Greek Island hopping Complete. For Now!
As I write this I’m sitting in my house in Paros, cats snoozing happily on the sofa. We made it through the summer and I feel that I can genuinely tick off number 8: Go Greek Island Hopping from the 50-Before-50 Bucketlist.
In the spring, we’ll be starting again. I’m serious about my new quest, a whole bucket list dedicated to visiting every inhabited Greek island. I want to visit all of them because they all sound so varied and interesting. I’m loving writing about the islands on my Greek Island Bucket List Travel blog. If you want to follow along there or find out more about each of the islands, that’s the place to go.