She looks at us aghast. She’s horrified.
You can’t do that! She says.
It’s a really long way! She says.
It will take hours. It’s not possible. She says.

We’re in a souvenir shop in Fira, one of many clustered around the cable car station that carries passengers from the old port below up to the town perched on the cliff 400 metres above. We’ve asked the young woman who works there if she can help us find the beginning of the walk to Oia, which is some ten kilometres away, but clearly she can’t, so we walk on.

A couple of stores down we ask again and receive the help we need. The older gentleman who works there knows all about it and points us in the right direction. We follow the path through the town for about half an hour, asking along the way. We want to be sure. The streets of the town are a labyrinthine maze that follow the contours of the land as buildings vie for the closest place to the edge of the cliff, and the views. Finally satisfied that we know where to go we head home. Tomorrow is the day!

Up at six. A cup of tea and a quick light breakfast and we’re ready to go by seven. Early morning is best to beat the heat. We’ve stocked up on a sandwich each, and juice and water. We’re all set.

Initially the path is through the winding streets of Fira,





and for the first couple of hours we’re in Fira, and then a bit to the north in Firostefani, and then Imerovigli. Our destination is Oia, at land’s end, where the inverted “C” of this island comes to a tip that steeply slopes down to the water. For most of the trip we can see Oia in the far distance enticing us forward.





These four towns on this western side of Santorini are all white buildings sculpted to fit the curves of the cliff, stacked one atop the other, clinging to the edge, all swish hotels with wide decks and infinity pools facing the water, all blue domes, blue doors, cascading bougainvillea. There are a million insta-worthy views here; every turn is a different postcard.








We are not aware of leaving Fira and entering Firostefani so closely are they huddled together. It’s a steep climb up but we barely notice; it’s the beginning of the day, I’m full of enthusiasm, and the view is glorious.





There’s a path we follow that meanders more or less along the rim of the caldera. Sometimes it’s a bit confusing but the general direction is north, with the water on our left. We barely ever lose sight of it. I am energized and happy. Don not so much.

From Don’s notes: 8 June 2022. The path initially involves walking on pavement past dozens of high end accommodations. There aren’t many people around, apart from the maids and cleaners doing their early morning routines. There are a few men moving large bags of hotel supplies on oversized dollies down steep flights of stairs. What a way to make a living! Something about these monuments to conspicuous spending irritates me and I’m feeling grumpy about us not being on the wilderness trail that I had expected to be walking.

That is yet to come.

There are cobblestones between Firostefani and Imerovigli,





and a bird nesting in a hole in the wall.





Soon enough we’re again back in the white beauty of a town: blue domes, arched doorways and roofs, and everywhere stairs leading up or down.





We see a couple of wannabe instagram influencers: the woman in blue above and the one in red below, the photographer arranging her dress just so. She sees me photographing her and gives me a wide smile, clearly enjoying herself.





I’m so naive, so out-of-touch with that world. It was not until researching this post that I discover that they pay for it. All those perfect shots of perfect young women dressed in long prom dresses, usually red, posing in all the iconic places around the world. I always thought to myself They travel with that dress? They stuff that dress in their luggage? Really? But no. They actually pay for a photo shoot. In Santorini it costs about $500 for the photographer and another $200 or more for dress rental. Quietly shaking my head. Not so much because they’re doing it, but because that’s what sells, that’s what gathers all the likes and loves and shallow adoration, and for the very very few an income. Maybe it’s a generational thing, but I don’t get it, and I don’t much like what they’re selling – women objectified. Again. But then the men also have their own insta perfect pose. It’s macho dude – in designer hiking clothes and backpack, back to the camera, at the top of a cliff, facing out to the void, one leg slightly bent, owning the world. I don’t actually have a shot of that though I’ve seen a few. I must get Don to pose for me one day!

Anyway moving on – to find a path through the convoluted town of Imerovigli; there are several to choose from. We stick as close to the water as we can, pass the occasional burst of flowers with a tantalizing view of the ridge to come,





and finally leave the town.





We’re on cobblestones now for quite a while. As we pass a couple of outlying hotels and resorts we have a clear view of the ridge ahead with the water to our left, and also at last we see water in the distance on the far side of it. We have come to where the land curves around forming the top of the backwards “C”.





This ridge is what we walk along, all the way to Oia. This is what Don has been waiting for. Truth be told, me too.





Our first goal is the church near the top of the hill.








Finally we reach it, this diminutive Church of Ekklisia Profitis Ilias, in the middle of nowhere.





We are grateful for it. We cannot go inside but it casts a shadow, the first shade since we left the towns, and a wall to lean against as we sit for a while, glad of a rest, a bite to eat, and water. Slowly we’re emptying our water bottles. We know we still have a long way to go as we look back to where we’ve come from.





There are tricky uphill and downhill sections with loose gravel underfoot. It’s challenging. In places the old cobblestones have worn away, breaking down to loose rocks. The path requires much attention and negotiation; it doesn’t let us walk easily.





We come to another church, the Chapel of the Assumption of the Virgin.





On and on we go – over gravel, over dirt, over loose rocks, occasionally passing others who are headed in the opposite direction.








And always there’s the view: the islands, the luminous blue water, and the wide blue sky. This is the best of Santorini, silent, peaceful, apart.

We walk ever onwards, each step bringing us closer to the town,





until at last we have arrived,





four hours after leaving Fira, hot, exhausted, and thirsty.

There’s a wide pedestrian boulevard that runs alongside the water the length of Oia, lined with shops, galleries, hotels, restaurants, and cafes, and we walk along it until we find the perfect place for brunch.





Don again: Orange juice, a strange but tasty meal of scrambled eggs, feta cheese, and baby tomatoes on a toasted sweet bun, then coffee for Alison and Earl Grey tea for me. Happy at last. We then go looking for a particular view of some blue-domed churches. Google maps was singularly unhelpful in directing us to them, but eventually after going in the wrong direction for a while we backtrack and find what Ali’s looking for.

It’s one of the classic instagram shots of Oia, and quintessential Santorini. Maybe I’ll actually post it on instagram. Or maybe not.





This also is quintessential Santorini.





Look how far the town slides down the cliff to get the best of the scenery, of that infinite azure beauty – all those fancy hotels with view decks and infinity pools, in their own way adding to it.

And it’s all accessed only with stairs – narrow paths, so narrow they can barely fit two people side by side, and stairs crammed into every last possible space.





We walk the length of the pedestrian boulevard along with a few dozen other people,








all the way to the ancient castle at the end, and a view of another classic instagram shot of Oia – the ancient windmills, once used for milling flour, but now converted to homes and hotels.








And from there also, a view back to where we’ve come from, the rugged ridge that curves back around the caldera to Fira.





Don again: After ice creams we find the bus stop to get back to Fira, and join a really long queue. A bus to Fira soon comes and the queue begins to move slowly forward. We only get half way to the bus before it’s full and takes off, but then the ticket seller tells us that another bus will be along in one minute. Hooray! The next bus arrives and we manage to get seats together towards the back of the bus, which continues to fill until it’s standing room only. The bus trip costs 1.50 Euros each for the 30-minute trip, our first, and possibly only, bargain on Santorini. I’ve walked a total of 24,793 steps today; a new record for me equalling 17.8km.

Through the magic and random happenstance of nature, back some 3600 years ago there was a monstrous volcanic eruption. As a result a fairly ordinary round island had a huge section blown out of the middle of it, creating a caldera, and leaving behind one small island, three even smaller ones, and this magnificent magical crescent-shaped one known as Santorini. The walk from Fira to Oia really illustrates the unique topography of the island, and shows us through the ever-changing infinite sapphire views just how special it is.

Walking from Fira to Oia is the best thing we do on Santorini. No wait; we also do a sunset cruise in the caldera. That’s pretty special too – next post.









All words and images by Alison Louise Armstrong unless otherwise noted
© Alison Louise Armstrong and Adventures in Wonderland – a pilgrimage of the heart, 2010-2023.