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  • Writer's picturetruemantravels

Chasing The Santorini Sunset

Updated: Mar 14, 2023

In life, there are moments that we cherish above all else. When we recall their memory, we are temporarily transported back to a breath of time that made us feel alive. These moments carry a warmth; a nostalgia like a familiar song. Today I want to share one of my moments with you.


If you’ve ever Google searched “Top 10 Things to Do in Santorini”, you would know that one of the most popular reasons to visit the Greek island is the famous “Sunset in Oia”. The stunning village of tiny white, blue roofed houses steeped romantically against the backdrop of the ocean and horizon is well known for it’s unobstructed view of the sun sinking into the Mediterranean sea. It’s also quite common that visitors (particularly backpackers) choose to stay in the town of Fira during their visit rather than Oia, because the cost of accommodations is significantly lower. Certainly, you could take the half hour bus ride from Fira to catch the sunset in Oia, but if you’re up for an adventure, embarking on the 11 km hike to Oia instead, is an experience you’ll never forget.


Sunset in Oia

The Path to Oia

I won’t sugar coat this for you; the path to Oia is long, uneven, strenuous and if you’re visiting in the summer like I did, the heat is almost unbearable. It begins with the cobbled streets of Fira winding through the shops that overlook the sea. The path is clearly marked with small wooden signs, directing you to the beginning of your journey.


Wear sunscreen, pack water, and don’t forget your camera (obviously). There is no shade and 90% of this hike is uphill. As you begin winding your way along, keep in mind that you’ll pass through a few small towns on the way that you might want to stop at for a water or bathroom break. Imerovigli is a particularly picturesque location en route with several shops and restaurants. It offers breathtaking views of the Caldera in itself, but fight the temptation to beat the heat and hide out here - the best is yet to come.


Skaros Rock

After a water break in Imerovigli, we were told by the friendly cashier that we couldn’t skip over the incredible views from Skaros rock before continuing to Oia. Skaros rock is right in Imerovigli and didn’t require much of a detour. It’s inadvisable to seek this out after dark or in inclement weather as the rock juts out high over the sea and the path is narrow. If you’re hiking in daylight and good conditions, I’d really recommend adding it to your itinerary on the way to Oia. Breathtaking views of the Aegean await you if you make your way out to the top of this old castle fortress. I’m sad to say that while Ramin, who I was traveling with, hiked out to get a glimpse of this view, I remained on the steps leading to Skaros attempting to find shade behind the rocks. I had picked something up on the plane and was very sick with a cold and probably a fever; the hike was already something I should not have been attempting but I’ll be damned if I was going to travel half way around the world and sit it out. So I sat on the stone steps in the shade, waiting for Ramin to come back, pressing a lukewarm water bottle to my forehead and hoping the lizards running around me weren’t going to decide to scurry up the legs of my flowy elephant pants.


In that moment, I felt really homesick. And I felt guilty for feeling homesick when I was in such a beautiful place, on an adventure I had been dreaming of for months. I really didn’t know how I was going to keep hiking because we hadn’t even made it halfway and my body was screaming at me for staying out in the intense 40 degree heat when I should’ve been in bed. I forced myself to stand up and I moved out from behind the rocks offering shade to take a look at the view. There was a momentary breeze off the water that cooled the sweat on my burning forehead. I took a deep breath, reminding myself to enjoy it. I saw Ramin coming back and moved into the shade to wait.


A Pack of Wild Dogs

My spirits picked up after Skaros rock. A mental kick up the backside and the sun lowering in the sky as we approached 5:00 pm allowed me to enjoy it more. The path changed from cobbled stones and staircases to dirt and uneven rocks. I cannot stress enough that you, unlike me, should wear PRACTICAL HIKING SHOES. Even if the blue Keds look really great with your outfit, it’s probably not worth it. Take my word for it. I was reminded of the stones on the black sand beach as I felt the path, uneven through my shoes, digging into the balls of my feet. But I really didn’t care - with the breeze cooling me down a little I was able to enjoy the magnificent view as we climbed to a higher altitude. As we rounded a bend the streets and land down below looked like a tiny grid, as if we were viewing them from an airplane during take off.


Then we noticed a cave in the side of the rocks. Shade. We eagerly approached the opening and were halted in our tracks by a low growl. A dog was lying just inside the entrance way, escaping the heat. We took a small step closer and craned our necks to get a better look inside. Another snarl echoed from inside the cave. My stomach dropped as I realized there was at least twelve dogs lying inside, likely many more as it appeared to be massive.


“Can we go? Now.” I was already backing away and continuing on the route. I love dogs, but I know that a pack of strays may not love me. Especially not encroaching on their cave.


We hurried away, onto the next leg of the adventure.


Uphill from here...

Seaside Hotels and Donkeys

As the path turned to dirt, precariously close to the cliff edge, the views of some of the hotels close to Oia evoked some serious jealously from me. If you’re on a tight budget, Fira is the place to be. But if you’re not...well I really don’t think you’ll ever get a better view than some of these cliffside villas with infinity pools overlooking the Caldera. We passed a man offering rides the rest of the way to Oia on his donkeys. Not interested in paying for that, we declined, and as we were walking away witnessed him whip one of the donkeys for what I would say, was absolutely no reason at all. It jumped away from him nervously, rearing it’s head.


After witnessing that, I question how these animals are treated. I know it’s a recognized form of transportation in Greece, particularly up the steps to and from the harbour ports, but I really had no desire to try that out with the thought of potentially unkind treatment brought to my attention.


Death of a Go Pro

The heat killed Ramin’s Go Pro. In the midst of filming a clip, it’s screen suggested it was “saving”, and remained this way, refusing to even turn off. Hoping everything had not been lost, it was stowed away in our backpack out of the sun. The Greek sun is no joke; the painted control settings on my DSLR were melted off in Athens because I kept it out of the bag too long. So again, I’ll remind you to bring lots of sunscreen. Being as pale as they come, it was already too late for me and no amount of sunscreen could counteract my vicious Santorini Sunburn. Aloe Vera became a priority for when we finally reached Oia.


After putting the Go Pro away, I suggested we stop briefly for a drink of water and a breather. I sat on a rock and looked out at the view. We were so high up and the Caldera was so vast. The sea stretched as far as I could see and the islands were a dark blue silhouette on the horizon. I didn’t care that I was sun burned, and sick, and my clothes were literally wet with sweat. In that moment I felt so grateful to be alive. I was stunned by the beauty of the world we live in and struck by how small we are in comparison. I was acutely aware that I am a drop in the ocean. Every minute of overtime worked to get the time off, every penny spent on the trip, I knew, was absolutely worth that feeling. And I was very lucky to share that moment with someone who felt the same way.


Caldera Views

The End In Sight

We finally crested the last hill and could see the town of Oia down below; it was 7:00 pm and sunset was fast approaching. The path had turned to cobbled stone again and the dry landscape was cacti and small lizards. Picking up the pace, we finally entered the small town and made a stop at a grocery store for Gatorade and Aloe Vera.


Are we there yet?

Santorini Sunset

After an 11 km hike where we had seen almost nobody else (probably because they knew it was too hot to be hiking), it was a bit of a shock to realize we were not the only people chasing the Santorini sunset. Oia was packed with tourists hoping to get a prime view of the crimson horizon that evening. It was tough to find a place to stand and we had to settle for trading out spots with some friendly tourists to get a proper glimpse. If I’m honest with you, I enjoyed the hike more than the sunset. The sunset was beautiful, and in off peak season in a more private setting, I think it would be a more spectacular experience. As the sun went down and the crowds of onlookers applauded, the hike caught up with me. My head was pounding and I felt extremely nauseous.


We made our way back into the heart of Oia with the crowds in search of Gyros. The number of people who came out to watch the sunset was so great that the streets were as packed as a Toronto subway car at rush hour. Moving at a pace determined by the people pressed up against me, I was suddenly pushed to the side, against the wall of a building. Turning around to see who was being so rude, I realized a rogue donkey was parting the sea of people, causing a panic as it charged through the crowd, likely as alarmed as we were. I don’t know who pushed me, but I’m grateful they stopped me from being run over by a mule.



Searching for Souvlaki

As it turns out, accommodations are not the only thing that’s significantly more expensive in Oia. After sitting down to dinner at a restaurant, Ramin and I determined we could not justify purchasing more than some bread and Tzatziki. I downed some water hoping it would help and we headed to the bus station. No way were we hiking 5 hours back to Fira in the dark.


The bus ride was short, 30 minutes, and cost us roughly 1.60 EURO each. City buses in Santorini are unlike public transit anywhere else I’ve been - they are coach style buses and I’ll warn you that the height of the bus in combination with the twisting roads doesn’t help a nauseous stomach.

By the time we arrived in Fira, the idea of eating was completely unappealing but I knew after such a hike, it was important. We found a delicious fast food style place to get Souvlaki on a pita, and then made a pit stop at the local drug store where I couldn’t read any of the Greek labels, and was forced to have blind faith in the pharmacist’s directions.



Lucky Souvlaki in Santorini

Finding Your Moments

Health wise, the day was down hill from here for me. My body paid me back for putting it through it’s paces with a fairly sleepless night. But I don’t regret that hike for a second. That fresh air, the view and that one moment of realization looking out at the Caldera that I recall fondly on a regular, made for an adventure that I will cherish for a lifetime.


I find traveling creates many of these moments. It forces you out of the routine of your daily life and the surroundings that become so familiar we start to take them for granted. It’s a fresh perspective and a chance to look at the world with new eyes. I encourage you to find your moments. You don’t have to travel far; a hike at a local conservation area can be just as good as hike in a foreign country. Your perspective changes everything.

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