Attempting to Ride a Donkey in Santorini

Last Updated on 06/30/2017

People always talk about how beautiful Santorini is… I’ve seen countless photos of the caldera and the iconic cliffside sprinkled with cerulean blue domes. No one really talks about the donkey rides in depth though… Or the stagnant humidity. I have never sweat that much in my life. Considering I’m someone who regularly participates in the self-torture that is hot yoga, that is saying a lot.

I stayed in the idyllic and effortlessly picturesque town of Oia with my mom. We hiked down the cliff to get to the swimming area around the corner from the seaside restaurants in Amoudi Bay. As we passed the donkeys, my mom said we would be taking those up after lunch. I hoped she was kidding. As a rule, I try not to come into close proximity with livestock or animals larger than me. Considering I’m about the size of a 14-year-old, this is problematic for even large breed dogs.

After following the trail past the restaurants, we arrived at a swimming spot and watched those more brave than us dive off the rocks. Along with the beaches on the south side of Santorini, this swimming spot is not be missed. You will definitely NEED a place to cool down. So if you are not lucky enough to have access to a pool at your accommodation, this swimming area is the spot!

I’m usually more oriented to food and cocktails than swimming, so as soon as we cooled down from the hike we headed back to the restaurants lining the marina. We had hummus and the most delicious dolmas at Dimitri’s.

My mom insisted her hip hurt too much to walk and she was taking a damn donkey back up the cliff… and she was not going down alone. So along with some European honeymooners, an Asian Instagram model, her photographer/beau and my mom, we took the trail. At first, there was the normal, uneasiness you’d feel when on a donkey climbing a steep incline. That was quickly drowned out by panic when the herder started bringing up the rear and all the donkeys surged up the hill. I tried to take in the views of Santorini…. Focus on the horizon? Is that what they say?

The 6 of us clung to our reckless, drunk donkeys charging from one side of the path to the other, mowing pedestrians down in our wake. As my donkey took a corner, he also decided to assault some innocent souls by bulldozing them into the stone walkway. I could only scream out in horror, “Sorry!” as this poor woman just pushed into the side of the donkey, back against the walkway to keep from going down. The damn honeymooners kept trying to hold hands. Guys. Now is NOT the time.

I hunkered down and attempted to snap a few photos. I was feeling brave and inspired to capture the moment like the oblivious and giddy Instagram model. My vain attempts were foiled…

This all came to an abrupt halt about 50 steps before the village, appropriately right at the sign that said “No Donkeys Allowed.” As everyone waited to be helped off, most of the donkeys just stood still, swaying slightly (I would say “with the breeze” to make the moment feel more tranquil, but there was no such tranquility or breeze). Of course though, there were two jackasses still charging aimlessly, yet with angst… the way a pack of frat guys would disseminate after a long night of beer pong.

What goes up must come down, or in this case, who walks down has to come back up. Sure it was quite the memorable travel experience, but had I not been with a senior citizen I would have taken that path like a StairMaster. Also, it was brought to my attention later that you can take a taxi. Special thanks to my mom, ever the adventurer, who sponsored this $5 escaped with Disoriented Donkeys Incorporated.

Are you heading to Santorini soon?… Be sure to check out the rest of my tips in the Santorini Travel Guide.