Athens & Santorini: A Winter Adventure
February isn’t exactly peak tourist season for Greece — but that’s when I had my two weeks off. I was living in Beijing at the time, and my friend Liza was flying in from Toronto. We planned to meet in Athens, then spend two weeks zig-zagging across the country.
Now, Liza made one thing clear before we even booked tickets: “It’s your trip, you plan it. I’ll just tag along.” Honestly, I didn’t mind. I’m the kind of traveler who actually enjoys organizing buses, ferries, and accommodation, and I already had half the trip sketched out in my head. Liza was happy to follow my lead, which worked for both of us.
I’m an organized traveler, but I also know things rarely go 100% smoothly. That’s why I didn’t book every guesthouse in advance — I left room for flexibility. In Greece, especially, bus schedules don’t always match what’s posted online. That wiggle room would prove very useful.
Another day, another town — hauling bags, chasing buses, and loving every minute.
When Plans Collide
Our flights were supposed to line up perfectly, just two hours apart. Instead, Liza’s plane was delayed by nearly ten.
I landed first, found our Athens guesthouse (which wasn’t quite like the photos, but after some complaining I scored us an upgrade), and wandered around the Parthenon area. I caught the sunset over the city, scouted where to buy tickets the next morning, and waited for her to arrive.
By midnight, she still wasn’t there. I thought I’d be helpful and wait for her at the bus stop. One bus came. No Liza. Another. Still no Liza. A third. Nothing. My stomach sank. What if something happened?
After nearly an hour, I gave up and rushed back to the guesthouse for Wi-Fi. And there she was — safe, furious, and banging on the door. Turns out she’d met some people on the plane who offered her a ride. She thought I’d be waiting at the guesthouse; I thought she’d be on the bus. We’d both been panicking in different corners of Athens.
She was mad. I was just relieved.
My first evening in Athens: just me, the Parthenon, and a golden Greek sunset.
Olympic Gear & Early Nights
Liza had flown in from Canada carrying fresh Team Canada Olympic gear — matching hats, mittens, and sweaters straight from home. It was the Winter Olympics at the time, and I was ridiculously excited to see them. We swapped clothes that night, but didn’t stay up talking. After the travel chaos, we went straight to bed. Tomorrow was our first full day in Athens, and I had every minute planned.
Twinning in our Canada gear, freezing our way to Santorini.
Sunrise at the Parthenon
We woke up early, bundled into our new Canadian gear, and headed straight for the Parthenon. The gates hadn’t even opened yet, and we were among the first inside. For a while, it felt like we had the place to ourselves — two Canadians wandering through ancient ruins in matching mittens.
The magic lasted until I ducked into the bathroom. I washed my hands and somehow managed to splash bleach across the sleeve of my brand-new Olympic sweater. I’d literally only put it on that morning. For a moment, I wanted to cry. Then I looked at the ruined sleeve and thought: at least it makes a great story. A very Canadian Greek tragedy.
A little bleach, a lot of history — still one of my favorite memories from Athens.
Temples, Markets & Local Lunch
From the Parthenon we moved on to Hadrian’s Library and the Agora. By then our legs were tired and our brains full of ancient history. Luckily, we had lunch plans.
A friend’s sister, an anthropologist working in Greece, met us on her break. She filled us in on details about the ruins and the lives of the people who once lived there. We asked her a million questions and devoured plates of food in a little taverna packed with locals.
After lunch we walked over to the Temple of Zeus and then wandered through the bustling market. By evening, we were wiped out. We didn’t want to stay up late anyway — the next morning would be an early one.
Just me, some 2,000-year-old ruins, and a lot of enthusiasm.
Valentine’s Day in Santorini
The following morning we navigated the chaos of the Athens ferry port. Online schedules suggested ferries only ran on certain days, but at the dock it looked like everything was operating. Confusing, but in our favor.
We boarded the ferry, and as the sun began to rise over the water, I leaned on the railing and watched the horizon turn gold. By the time we reached Santorini, I knew the trip was about to shift gears.
Our guesthouse — The Fisherman’s House in Akrotiri — welcomed us with rustic charm. By sheer luck, it was February 14: Valentine’s Day. We cracked open a bottle of sparkling wine and went out for dinner. Not exactly the candlelit couple’s scene you’d expect, but hey, nothing says romance like two Canadians in Olympic sweaters.
Chasing the sunrise across the sea on our way to Santorini.
Time Travel in the Rain
The Akrotiri archaeological site was just a short walk from our guesthouse. We bundled up and headed out, bracing ourselves against the February chill. The wind whipped around us, and at one point, showers passed through, but it didn’t matter — the site was incredible.
Unlike most ruins, Akrotiri lets you actually walk through the streets, the same ones ancient people once used thousands of years ago. I remember pausing and imagining what life must have been like there, hearing the rain tapping on the roof of the protective structure while wandering past walls and doorways frozen in time.
Afterwards we wandered down to Santorini’s south beach, with its dramatic dark sand and waves rolling in under gray skies. Cold, windy, but beautiful.
From cliffside views to ancient ruins and black-sand beaches — Santorini was more than just postcard-perfect.
Staircase Roads & Oia Sunsets
In the afternoon, we rented a car to see more of the island. At first, everything went smoothly — until Google Maps betrayed us. We were trying to reach the castle in Akrotiri, and the road kept narrowing, tighter and tighter, until finally… it ended in a staircase going straight up.
I insisted the whole way: “This is the right road!”
Liza: “JD, it’s getting smaller…”
Me: “Trust me — it’s fine.”
And then we stared at a flight of stairs where the “road” should have been.
It’s a story Liza still teases me about — and probably always will. My classic Santorini mishap.
That evening, we joined the fairly large crowd in Oia to watch the sunset. Even in February, people gathered from all over the island for that moment. The whitewashed houses glowed orange against the sea, the sky shifting through pinks and purples before the sun disappeared. We shivered in our Olympic sweaters, surrounded by strangers, but the view was pure magic.
From getting lost in narrow alleyways to finding the perfect view in Oia — every wrong turn in Santorini came with a reward.
Stranded, but Not Alone
That evening we returned to the ferry port, bags packed and ready to head back to Athens. Only when we arrived did we learn the bad news: our ferry had been cancelled. We found other backpackers waiting at the dock and they got the news at the same time. Suddenly, none of us had anywhere to go.
For a moment there was panic, but then — travel magic. We all started scrambling together, trying to figure out what to do. None of us had a plan. The backpackers remembered a hostel they’d stayed at the night before, so we all piled into the car and headed there, fingers crossed that there’d still be space.
Luckily for us, there was. Liza and I ended up with our own private room and shower — not exactly the “full hostel experience,” but close enough for her first time. (The real hostel experience would come later in Meteora!)
To make the night even better, the rental car company told us we could keep the car until the ferry departed the next day at no extra charge. It was such a simple gesture, but one that saved us the stress of returning it in the chaos of cancelled travel plans.
The next morning, with unexpected free time, we wandered Oia again, this time in broad daylight. Wrapped in our Olympic sweaters, we ducked into a café overlooking the caldera, ordered steaming mugs of hot chocolate, and just sat there, soaking up the view. The sea stretched endlessly below, quiet and moody under the winter sky.
It wasn’t the day we’d planned, but it became one of the most peaceful moments of the whole trip.
Who says Greece is all sunshine? Hot chocolate weather in Oia was its own kind of magic.
It felt like our adventure was back on track — but if there’s one thing I learned in Greece, it’s that travel plans never stay simple for long.
Next stop: chasing ancient myths in Delphi and climbing the cliffside monasteries of Meteora.
💡 JD’s Tip: In Greece, don’t lock yourself into a tight itinerary. Ferries get cancelled, buses sell out, and sometimes you end up sharing a hostel with strangers who become part of your story. Leave room for surprises — they often turn into the best memories.
