48 hours in oia.

For as much as I've traveled in my life, one thing I hadn't done until this year was travel alone. Sure, I've been on plenty of solo work trips, or taken flights by myself to meet a waiting group at the destination, but as of this past March I hadn't actually gone on vacation alone. I don't know what took me so long. It was incredible.

For the past couple of years I've been traveling back and forth to Paris for work (13 times in just under four years, to be exact). Although Paris will always and forever have my heart, every time I go to get on that dreaded flight across the ocean and wish I was en route to explore somewhere new. So, finally, with a nod to my "year of yes" (as well as a very strong desire to start checking things off my list before I turn 30) I decided to do something about it. Greece has been at the top of my list of places to see for years now. First and foremost, Greek food is my favorite. But also, how can you not be drawn to those beautiful blue waters and incredible white homes lining the cliffs. My family had visited Oia the summer prior, and after hearing all about it I knew I had to make my way there as soon as possible. So, following my March Paris trip, I hopped on a flight down to Santorini where I spent an incredible, and much too short, 48 hours.

Although absolutely worth it, Oia is a trek. With only a couple of flights a day from Athens, more likely than not you'll get stuck with a pretty significant layover, as I did. During the summer I hear there is a ferry you can take to the island, but as I went in the off season, flying was definitely the best option. Unfortunately though, this meant losing almost a full day to travel. Arriving on Santorini, it was still another 40 minute taxi ride into Oia, where I was met by my lovely Airbnb host who walked me up and down and around the weaving streets of the village with my suitcase on his shoulders, eventually making it to "Casa Sofia", my home for the weekend. I was warned that due to the off season most restaurants and shops were going to be closed, and that was certainly no exaggeration.  Finding just one open restaurant in the whole village, I insisted on ignoring the cold and sitting outside. I was in heaven. Despite being my only food option, it did not disappoint. I mean, who doesn't love fresh veggies, real feta cheese and red wine? Besides one other couple, I was the only tourist there.  A few locals gathered in the back corner, and cats roamed freely - pretty accurately how I had imagined a sleepy old town would be sans tourists. Pitch black, it's actually a miracle I was able to make it back to the apartment after dinner that night. My host had pointed out one landmark only, so I was left to find my way based on essentially instinct alone (and a couple of wrong turns). Finally making my way back, I couldn't wait to wake up the next day to finally see the place in the light of day and explore.

As excited as I was, nothing could have prepared me for the disappointment I felt waking up that next day and realizing that the entire weekend was going to be cold and rainy. I guess that's what I get for going in early March, but at least it meant I had the city pretty much to myself. Finding a small (the only) cafe open for breakfast, I continued on my trek of eating my way around the city. Fortunately I had the foresight to bring a book, as this cafe ended up becoming my adopted home for quite some time while I tried to wait out the rain. As luck would have it, I wasn't the only one, and was fortunate enough to strike up a conversation with another solo traveler who was there checking in on his rental property before tourist season. A property owner on the island, he had been coming to Oia for years, and graciously offered to take me on a tour of the island to see some of the other towns, get the best baklava on Santorini (in his opinion), to stop by the black sand beach and to see the infamous vineyards with sweeping views of Oia and the island. Stranger danger be damned, it was a lovely way to spend the afternoon, and we actually caught a small break of sun while on the beach. A few hours later we made our way back to Oia where we parted ways and the rain had let up enough for me to continue getting lost wandering through the village. Although beautiful, walking around is not an easy task. Pretty much exclusively staircases, sometimes with stairs up to your waist, it's not for the faint of heart. Plus, you might get run over by a donkey at any time. One of the perils of the off season I'm told, as once tourist season starts the construction must stop and the donkeys have the summer free from hauling concrete and rocks. After an afternoon of trekking around, I was glad to sit down with a glass of wine (and more food, obviously). I quickly learned that part of traveling alone is making friends along the way, and I began chatting with a local who offered to show me around a bit more. Heading up to the op of the island, I found myself at the most beautiful church, full moon above and sweeping views of the town below. It's a little bit amazing what kinds of places you'll find yourself in when you open yourself up to the possibility.

Waking up the next day I was thrilled to discover the rain had stopped, but became less thrilled when I was told that the power in the entire village had gone out. No lights and no hot water at home, and no food being served in the village, I cut my losses and tried to enjoy some quiet time alone, a rarity at that point in my life. One full viewing of Cruel Intentions later (what I can say, it was the only thing on my laptop), the power came back on and my day could finally start. I headed out with great intentions - I so badly wanted to climb down the 300 steps from the top of Oia down to Amoudi Bay harbor, however, the weather had a different plan in mind. Just about halfway down I realized that there was a good chance I'd get blown off the cliff should I continue. So, begrudgingly, I returned to the cafe with the wine and the feta and pretty much spent the rest of the day there reading. Things could have been worse. 

Leaving Greece was not easy. The place - as cold, rainy and empty as it was - will always and forever have a special place in my heart. I’ll never forget the donkeys roaming the streets, the taste of fresh feta, the scent of saltwater lingering over the whole city. The sweeping views of the iconic architecture will stay with me forever, as will the generosity and kindness of the locals that made my first solo vacation even more magical than I ever thought it could be.

Greece, I love you, and I’ll see you again soon.