A Brutally Honest Guide To Sunset In Santorini

You know those "Pinterest fail" photos, the ultimate depiction of expectation vs reality?

If these perfectly formed cookie monster cupcakes are Santorini, then these amorphous blue blobs are my experience there.

Don't get me wrong, Santorini is beautiful, picturesque, and perfect for those glamorous individuals who thought to pack billowy gowns, strappy heels, and dangly golden jewelry with them.

I was not one of those people.

I had a good time in Santorini, outside of town, exploring the cliffs and beaches, and watching the sunset from the hilltop by my hotel.

But while exploring the city of Oia I felt like a puppy in a business meeting.

In fact, my somewhat disappointing time in Santorini was one in a series of factors that lead me on a completely unplanned and unexpected journey to Iceland. More on that here.

Tourists in Oia play dress up. They play dress up hard. And for me, it felt icky, phony, forced. The expectation is of exclusivity and glamor, and to feel like Greek Goddesses overlooking the city and the boats far below.

The reality is that there are thousands of sweaty people, shoulder to shoulder, strangers getting poked in the eye with selfie sticks, and people dressed up as Instagram models taking itty bitty cautious steps as they slip and slide down slick and steep streets. Sorry for all those ss. 

Now, that sunset.

Author: Karol M License: CC BY 2.0

Author: Karol M License: CC BY 2.0

After fighting your way through crowds of people who can barely walk in their heels, you have to try to find a spot.  I scaled a building to get one, and there were plenty of people stuck behind this wall, just reaching up to see the sunset with their cameras. 

I don't mean to sound negative or cynical, but Santorini (Oia) is not for me, and unless you are actually wealthy, you probably can't afford one of the hotels you've seen in the pictures. You won't be directly in town, your hotel won't be white with a blue roof, you won't have a private infinity pool (you might not have a pool at all), breakfast won't be included, and there's a good chance you'll feel out of place.

There are beautiful sunsets all over the world. I think there's something a lot more magical about finding your own once-in-a-lifetime sunset than waiting in a Disney-world-like line for one that a million other people are elbowing you to see.

My sunset was about five minutes out of Oia (pardon the shorts, I was "doing laundry"). I sat by myself with a beer, the sky turned to watercolor, and the solitary and unobstructed view actually felt once-in-a-lifetime. 

My advice is to get out of town. Discover the island of Santorini without getting caught up in the race to look cool in Oia. 

There are white beaches, black beaches, hidden stairways in cliffsides, donkey stampedes, and beautiful sunsets all over the island!

The best sunset I've ever seen was from my backyard in Kitchener, Ontario. Where was yours, and what made it special?

As always, thanks for reading, and don't forget to follow the sloth!

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