I Went to the Most Instagrammable Place on Earth – Expectations Vs. Reality?

Despite being outside and with a blustery North wind dancing across my face, I put on my mask. 

For the first time in my week-long trip through the Greek islands, the crowds had become too much for a COVID-concious traveler like myself to ignore. Throngs of people from all walks of life jostled each other through the narrow corridors of Oia on the island of Santorini in search of something special; a photograph. 

Not just any photograph, either. The consummate photograph where the wind’s playful gusts tousle hair and animate clothing while the immaculate blue domes and whitewashed homes cascade down the slope in the background. You’ve seen this photo before. We all have. It has become a staple for any social media influencer or model looking for an image to proudly display to their mass of followers – some real, many others purchased from bot farms overseas. 

What I Expected vs. What I Saw 

I don’t really know if I expected something different. Any Google image search for Oia shows a hundred variations of the same photo. Sometimes the subjects in colorful attire are staring wistfully into the distance, others are sharing a kiss as the western sunset douses the coastal town in an aureate glow. And really, who wears a dress with a 20-foot train? 


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Either way, the one thing to remember is that these photos are fake. 

The people in them are real. The landscape is indeed spectacular. But the fallacy appears in the very foundation of what it means to be a good traveler and a person who goes against the grain in search of experience outside the ordinary. 

They weren’t here to follow in the footsteps of the Venetians who hundreds of years ago harnessed the North wind to grind their grain via windmill.

These social media clout chasers weren’t here to understand the Minoan eruption of 3,600 years ago which formed the awe-inspiring volcanic caldera all around us and laid waste to life in the ancient Mediterranean. They weren’t here to follow in the footsteps of the Venetians who hundreds of years ago harnessed the North wind to grind their grain via windmill. And they most certainly weren’t here to appreciate, respect and immerse themselves in an ancient culture steeped in marvelous tradition and outstanding innovation. 

They were here to fake a picture then head back to their home on Main Street in Boringville. It was cringe-worthy in every sense of the term. 

A Tourism Economy 

While many are perturbed by this particular brand of “influencer media”, photos are big business in Oia and a significant source of income for some locals. For a few hundred Euros, a team of specialists will bring visitors to the most picturesque spots in town. Some even offer wardrobe changes and hair styling for clients who can’t afford to look drab for their following. While the photographer snaps away, a minion out of the shot will take the train of the model’s dress and flip it up into the air so it two-steps in the breeze for the microsecond it takes to grab a dozen still shots. 

Oia, Santorini

The results of a free photoshoot in Oia | Photo: Andrew Freeman

I tore my eyes away from the plunging cliffs and thoughts of hundred-foot high magma spouts to watch the displays of vanity with morbid curiosity. The operation ran like a well oiled machine. A group would step up to the shot location, spend a few minutes posing, primping and shooting while the next group waited patiently in line to do the exact same thing. A quick look at the final product and it was off to the next location to wait in line for more tiresome facsimile. 

It was a cookie-cutter, mass-market charade, smashed and blended, ready to be spoon-fed to an internet where the line between real and fake was indelibly smeared already. 

I chuckled, smirked and felt a looming sense of secondhand embarrassment for these people who spent hours traveling to one of the most unique places on the planet only to ignore everything about it that made it special. 

This wasn’t a travel memory. It was a cookie-cutter, mass-market charade, smashed and blended, ready to be spoon-fed to an internet where the line between real and fake was indelibly smeared already. 

I was visiting the island alongside travel writer Dana Freeman who has grown a following documenting her journeys for a number of well-known cruise and travel outlets. I spent the first part of the trip listening to her stories of a recent trip to Africa where the only aspiring-influencers around have four legs and stalk the great plains in all their majesty. This experience was quite different. 

Freeman found that the lust for the perfect photo took away from the experience altogether. Her advice to visitors? Get off the beaten path. 

“While Santorini is undeniably gorgeous, Oia is overrun with hundreds of influencers posing in ridiculous outfits to capture the perfect shot for their Instagram instead of admiring the beauty around them. They even wait in line with their crew to take their photo from just the right alleyway overlooking just the right rooftop in just the right sunlight,” Freeman said. “Who actually wears an evening gown to explore an ancient greek city, anyway. The scene impeded my ability to enjoy Santorini and is not the way I like to explore when I travel. Take me off the beaten path instead to a lesser-known Greek island any day and away from this absurdity.” 

Respecting the Locals of Oia

You could tell the locals were fed up, but also resigned to their fate having made their home inside a postcard. What you don’t see cropped from these nauseatingly perfect images is the signage from the local population pleading with the masses to respect their property. On the roof of blanched buildings all around the town could be seen signs in black and red spray paint all saying something along the lines of “Private Property: Keep Off”. 

It’s easy to see how an entitled Instagrammer could see the tiered white roofs of Oia as stepping stones down to the photograph of their dreams. It seems inviting to daintily step across roofs and over balconies in search of an angle nobody else thought to get, but what they’re really doing is trespassing. 

I didn’t see anyone get arrested for traipsing across private property, but I’m sure it’s happened to the hopelessly ignorant, truly revolting brand of traveler exploring this famous Greek island. 

My time in Santorini will live within me forever. The island is a delightful mixture of mind-blowing geology, entrenched custom and culture, and friendly people who were both thrilled and horrified to have a mass of tourists return to their shores after a pandemic-inspired hiatus. 

Traveling is about pulling yourself away from the mundane and rising up to an experience that doesn’t repackage the same tropes or violate the sacred respect between local and visitor. It’s the best way to make your trip one you won’t ever forget.