My Favourite Greek Island Moments: Mykonos, Paros and Santorini

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Greece is the holiday destination I am most familiar with, having travelled there with my family since I was young. I can reel off a long list of the islands I have visited. It was the place I chose to continue travelling to on my first holidays without my parents. However, the holidays were exclusively big beachfront hotels with maybe one day trip to see the island in a week-long holiday. So since I began solo travelling the desire to explore Greece more deeply would not let me go. This post is all about the moments that made me feel that I was truly in Greece, whether it was the big wow moments or quieter more simple pleasures. The moments that spoke to my slow-lane, sun-worshipping, crazy cat lady soul.

Usually I travel for 3/4 days which allows me to squeeze in as much travel as possible around work. But this time I wanted to take things slow, as the Greeks do. The idea of island hopping sounded so carefree, so hedonistic, I couldn’t resist. (Of course the ferries aren’t nearly as glamorous and carefree a way to travel as you think but more on that later.)

Although I had been to many of the Greek islands I had never visited the the Cyclades and the more I saw the distinctive pictures of blue and white streets, the blue domes of Santorini and the windmills of Mykonos, the more I was certain, it had to be them.

The islands I chose were Mykonos, Paros and Santorini. I chose Mykonos and Santorini because I couldn’t resist seeing the infamous islands for myself. There must be a reason everyone goes to those islands! And I chose Paros as a quieter contrast to the two popular isles. I was also definitely swayed by the pictures of pretty harbour town Naoussa where I stayed. After ten days I had so many memories and favourite moments to share with you but these are my Greek island hopping highlights, the moments that really stood out…

My Favourite Greek Island Moments

Disclosure: This article contains affiliate links. For every purchase made through one of these links, I receive a small commission, at no extra cost to you. Thank you!

1. Nights of Rain and Stars

On the second day in Mykonos it rained on and off and remained overcast for much of the day. An odd choice you might think for a highlight reel. However, it was the evening that was so memorable. I was sat outside a creperie (that also served as a bakery and bar!) watching people stroll by.

Inevitably it began to rain again. And rain some more. Until the owners started little by little dismantling the exterior and soon me and a small handful of other customers were huddled inside watching the rain pour. It wasn’t long before the water was coursing through the narrow whitewashed streets like a river.

There is a special feeling about the moment it rains after many many months. It feels like a turning point, change tingling in the air.

Of course I had come to Greece in October sans umbrella. My warmest clothing was a cardigan and the jacket I was travelling to and from England in. I was wearing a bright yellow maxi dress, perfect for trailing through sodden streets.

I began to wonder if I would be forced to sleep in a bakery on my second night in Greece.

Thankfully the rain paused long enough for me to squelch back to my hotel, gingerly padding through the damp streets. I then watched as lightning sparked across the sea. Magic.

2. Beach Tavernas of my Dreams

It became my mission to find the rustic Greek tavernas I picture when I think of Greece. I realised quickly that Mykonos was not about cute, simple tavernas, but pricey beach clubs with pristine finishes. Places all about name tags and selfies, that manage to make you feel inferior for rocking up in properly bedraggled beach hair and well-worn sandals.

The only proper beach taverna I found was not far from Mykonos town, Joanna’s Nikos Place on Megali Ammos beach. Although the service was mixed the atmosphere was relaxed and the setting as rustic as you get. My Greek lasagne with salmon was delicious and very cheap compared to other places I’d eaten in Mykonos. Although it’s nice to eat in fancy places when on holiday I definitely enjoy finding places where you can relax after exploring, swimming, or wandering around windy Greek isles!

My second beach taverna highlight was in Paros. I took a boat from Naoussa to Kolymbithres beach which was a haven in itself. Further back from the beach, past the official beach taverna was Taberna Vigla. It didn’t look anything exciting from the outside but Google Maps informed me it was highly rated. Because it was slightly further back from the beach it was higher up, offering an idyllic view over the sea. It was the perfect spot to snooze with a (small) bottle of wine through the afternoon. This felt like exactly the way to spend time on the Greek islands!

Greece has a way of making you slow down. Whether it’s with the beguiling cats begging to be stroked, or actually plonking themselves on your lap, or the lunches that stretch on and on until you realise its four o’ clock in the afternoon and you haven’t moved you’re so mesmerised by the ludicrously perfect blue of the sea.

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3. Hiking the Byzantine Trail in Paros

After so many languorous lunches and town-based wanderings I was so ready to stretch my legs and see some Greek countryside for a change.

The trail begins in the mountain village of Lefkes in Paros and takes you past stunning views over the hills to the sea and finishes in the village of Prodromos. The start is well signed and once you’re on the walk it’s impossible to lose your way.

I only saw a handful of other walkers on the route so it’s a wonderful time to escape the crowds and take some alone time with nature. I definitely felt invigorated and re-charged by the end of the walk.

The trail only takes 45 minutes to walk and is so easy to follow so it would be suitable for most people. Make sure you have plenty of water of course as there’s nothing between the two villages.

The village of Lefkes is a quiet and peaceful place and when I visited in mid-October it was well on its way to winding down for the season.

The other highlight that came with the walk was a rewarding piece of orange cake afterwards with mostly locals for company, plus one fiendish cat who was determined to steal my delicious cake!

4. Mornings in Naoussa

After the buzz of Mykonos the first morning in Paros felt so serene. I wandered along the harbour and stopped to sit on a bench and stroke a cat. It felt like the world had stilled. The morning sun at my back, a cat meowing, ducks ruffling their feathers: bliss. When I explored the little town I hardly saw another tourist until ten o’clock. I couldn’t believe the rest of the world had forgotten this charming nook of the Cyclade islands.

5. The Cats of Greece

They cannot go unmentioned – as they photobombed with style, snoozed on chairs, stole my cake or cuddled up against me. Anyone who’s been to Greece knows that the cats are everywhere. Basically if you don’t like cats, don’t even bother. Luckily for me I love ’em.

I found the cat’s of Paros were the most affectionate and cheekiest of the lot! One curled up against me in the port as I waited for the ferry as though it had never been cuddled before. There were also many that were more skittish, perhaps less used to tourists than their island neighbours. The cats of Mykonos were plentiful and definitely the biggest posers! They knew how to complete a picture. I saw less cats in Santorini than the other two islands. So if you want to plan your holidays around where are the most cats this is what you need to know!

6. First Glimpse of the Caldera in Santorini

Never has my timing been so perfect. I didn’t really know where I was going when I headed out of my hotel in Fira (facing the other side of the island). Having the sea so close on both sides definitely confused my poor sense of direction! When I finally got headed in the right direction I headed up a street, not knowing if this was the way to be for the prime spots.

It was simply a wow moment as the caldera below Fira came into view at the top of the street, just as the sun was sinking low in the sky. What an introduction to Santorini! I ambled along the main promenade and found that incredible views were in every direction! I understood then why Santorini has all the fame and glory.

What struck me was how relaxed and serene the main street was. I was prepared for hordes of people, battling over sunset spots. But Fira’s was a sunset of effortless beauty, blazing before you without shame. Everywhere I turned the view was sheer and white tinged with gold.

I do often find that it is the first glimpse that really stuns you. After that there is this weird sense of oh yeah, it’s there, I’ve seen it now. It’s incredible how quickly your eyes attune to beauty, as if they’ve never looked at supermarkets in the rain or concrete streets studded with chewing gum.

7. Sunsets to Forget

Memorable for all the wrong reasons was the sunset in Oia (pronounced ee-ah). It comes as the most highly recommended thing to do in Santorini but Oia was busy where Fira was quiet and confusing where Fira was simple. It did not work for me.

Now I’ll admit this was partly (or mostly) my fault as usual! After hiking from Fira to Oia (and taking my time over it) I was ready for a drink and a rest when I arrived in Oia. Even though I’d read the advice a million times about getting there early for sunset I still misguidedly believed I had enough time – I was there! The city was stretched out before me. But as I relaxed and sipped my aperol spritz the sun was sinking ever lower. So by the time I strolled casually deeper into the town I did not have time to figure out where I needed to be.

I had arrogantly believed that I could find the beautiful views easily, how wrong could I be! Oia is not a straightforward sunset view like Fira, it is a higgledy-piggledy maze of viewpoints, some poking out into shadow, having already lost the sun, and many already filled to the brim with crowds holding their iphones aloft to capture the sunset. And these were simple views of sea and sunset, perfectly lovely views but not unlike those you could find at much more serene spots.

Basically if you want to see the sunset from Oia and get really interesting photos with those blue domes etc, you need to plan. I really wouldn’t recommend doing what I did and heading there for sunset having never been to the town before and no clue where to be. I did read lots of blogs that identified the prime spots but I get so tired of having my eyes glued to google maps all the time I decided to just wander. But wandering Oia at sunset is not a good idea!

The sunset from Oia may be spectacular and photo-op worthy but as an experience I would recommend Fira instead. Of course if you are staying in Oia this isn’t really relevant as you may have a built in fabulous view from your hotel (lucky you) or be close enough to explore the town and find your sunset spot by day.

If you’re staying in Fira I recommend taking the bus and exploring Oia first thing in the morning instead. You can find the most beautiful places without the crowds in the way. And you could always do the hike back to Fira. Or! If you really want those Oia sunset pics just be super organised and efficient unlike me!

8. The Hike from Fira to Oia

Or as mentioned, Oia to Fira. Unlike the sunset in Oia, this was something that no-one could ruin and no time could hamper. Spending a few hours with views all along the caldera could never be a bad thing. The first part of the hike is very civilised, with several towns along the way where you can stop for a drink with an incredible view.

Once you’re past Imerovigli there’s nothing between that and Oia, a good couple of hours walk away. At that point in the walk many other walkers seemed to melt away, the girls posing for pictures only making it to Imerovigli. And certainly if you’re not a big walker or just don’t have time, walking that stretch along the coast and then spending time in the town and walking or getting the bus back would be ideal.

The hike took me over four hours because I stopped for a drink and took it really casually. It would be sensible to do it first thing in the morning (which I didn’t) before it gets too hot. This is definitely one of the best things to do in Santorini to give you another perspective on the dramatic scenery.

9. Swipe for a Local Guide

At the risk of over-sharing my penultimate highlight involved that well known app: Tinder. Tinder abroad might be firmly in the hook-up category but at least you get a more interesting experience out of it. For example I had never been on the back of a scooter before so zooming round Santorini on one was something I couldn’t leave off this list! I also find that it’s nice to talk to someone with local knowledge. Generally I find it hard to get chatting to people on my travels, whether local or tourist, so using an app is a great way to find conversation as much as anything else. Moonlit walks on the beach beat a drink at the pub anyway!

10. First and Last Sunsets in Mykonos

I returned to Mykonos at the end of my trip to catch my flight home and it was strange to come back and feel the island had a slightly different vibe. A few days later and the crowds were thinning, restaurants closing. The season was ending just as my trip was. It was not only the last sunset that was so special but the whole last afternoon as I laid on the beach and truly relished in the sand between my toes and the unearthly blues of the Aegean Sea.

My first sunset was full of anticipation and excitement, wonder at the brillance of it. When it came to the last I couldn’t bear to drag my eyes away, even when my phone died and I had to clasp my beach towel around my shoulders to keep warm. I knew it would be a long time before my eyes could absorb such beauty again. The grey, cold skies of England were waiting for me. I wanted to study every last ember of glowing sun.

But I knew it was only so special, more beautiful than all the perfect sunsets that had come before, because it was ending. Endings are painful, melancholy wrenches but they make the magic so much sharper. The ending made me stop, stop searching for a perfect sunset picture, stop thinking about anything else but that moment.

Useful Island Hopping Links

Ferryhopper – Plan and book your ferry trips

Booking.com – Find your accommodation

Bus Timetable for Paros

Bus Timetable for Santorini

Bus Timetable for Mykonos

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