In a conversation when we first started dating, Bryan and I learned that we both had the Greek islands on our bucket list. I had already been to Athens (with Jake in… 2011?) but hadn’t visited the idyllic, white-buildings-blue-shutters, crystal clear water islands of Mama Mia. When it came time to decide where we would meet this spring, it didn’t immediately come to either of our minds. We considered Japan (too much to do and see, we were going for a chill vibe), London (I’ve been, would go again if he really wanted to; but not very interesting), Italy (I could be persuaded to go again but I really wanted to go somewhere new), I suggested Morocco, Egypt, or another trip for Bryan to India. And then it hit me, “Greece!”
We originally planned for Athens, Santorini, and Paros but after finding an enthusiastic and popular Greek tour guide on YouTube and reaching out to him on Instagram, we changed our plan from Paros to Crete per his recommendation.
Bryan started his journey east on a Thursday, I left Bangalore heading north west on Friday. He landed in Athens a couple of hours before me so when I landed, we started texting immediately. Customs took a painfully long time but even as I stood in line impatient to get through it, I was laughing and smiling at my phone, giddy, knowing Bryan was a few hundred yards away. He asked what my new luggage looked like and I told him to guess (a test to see how well he knows me, of course). Once finally through security, I ran-walked to the baggage carousel and saw him. I think he must’ve seen me first but smiles broke out on both of our faces and I took on a sort of gallop to get to him. Straight out of a movie 😉 we hugged for soooo long, kissed, stared, hugged, laughed, kissed, stared. And yes, he guessed the right suitcase.
Our flight to Santorini was in a few short hours so we made our way to the check-in level, went outside for some fresh Greek air – and to welcome ourselves to GREECE. Before checking in for the flight, we stumbled on a coffee + ice cream shop right in the airport and I had my first affogato. Coffee over ice cream. The trip was off on the right foot. We checked in and headed for the gate.

I am writing this at the end of June, and the trip was in May. I wish I could remember the exact order of these next events but I cannot so I’ll keep it short…ish. We waited a couple of hours and then loaded a bus to the plane, loaded the plane and waited for takeoff. We sat on the tarmac long enough for everyone to get antsy and then, in Greek first and then English, we were instructed to get off the plane, back onto the bus, and back to the airport terminal. That was the first time Bryan and I looked at each other after a Greek-to-English announcement, baffled by the lack of reaction from the local travelers. We laughed talking about how if the English announcement had played first, everyone’s audible frustration would tell the other passengers everything they needed to know about the status of the flight.
Two more bus trips later (although none resulting in loading the plane again), we learned that the wind in Santorini was so bad that incoming flights had been delayed in hopes of a regular evening dip in wind speeds. We befriended an old solo traveler, an Aussie with a yoga retreat in Bali who was booked on an earlier flight to Santorini. After one bus trip to and back from the plane, we realized that he was nowhere to be found and learned that his flight had departed. The airline gave us food vouchers and we kept reminding ourselves that we were better off delayed together than one of us delayed somewhere, both of us alone. We sat near a woman (40s) and her daughter (20s) and were entertained by the woman’s insistence that we were being lied to, that the airline was probably understaffed and instead of admitting that (because then they’d owe us refunds), they had to wait for the earlier flight to get to Santorini and back to Athens with our flight crew.
Something like 6 hours after the scheduled departure time, we were taking off to Santorini and let me tell you: the turbulence was enough evidence to me that they’d been telling the truth.
We landed in Santorini, got our rental car and headed to the hotel. For Santorini, we opted for charm. A local resort on a hillside facing the caldera, white buildings and blue shutters as far as the eye could see. Of course it was 10 pm so we couldn’t see anything yet. We parked the car in what seemed to be the middle of a street but were told was public parking. It was insanely cold and windy, to our surprise. We dragged out suitcases down a dark, secluded, cobblestone alleyway – so loud for such a quiet night – not the least bit certain it was the way to the hotel. But it was – we found it and wound our way up and down stairs (we were definitely on a hillside) looking for reception. With Bryan frustrated (and probably regretting that he didn’t vet this location more), and me freezing to death, I left him to manage the bags and finally found reception. I heard our bags roll and crash outside as I got the room key and couldn’t help but laugh out loud at what I imagined was going on out there. We both laughed at us and the ordeal as we made our way to the room. Like a little hillside, concrete cottage.
We woke up the next morning to the view of all views. Picturesque Santorini, our room facing right out onto the bay and neighboring islands; we were on the top of the tallest ridge so could see northern Santorini and the sea on the other side of the island. Honestly, it was insane. And SO COLD. We had a private hot tub outside our room but sadly, it was far too cold to enjoy. Our breakfast was delivered and set out on our patio for a nice chilly meal. We took a stroll to the town just above the hotel, saw where we parked the night before and went to the nearby shops for coffee and snacks.
That day, we took the car all around the island, checking out different beaches and beach towns. It was a nice day (much less blustery closer to sea level) just exploring Greece together. It kept hitting me: we’re TOGETHER IN GREECE. Pretty special.
We spent a few nights in Santorini, breakfast delivered each morning, and exploring afterward. We spent a day in Oia running around to all of the famous picture spots. It was crowded with tourists but for good reason – the town is quintessential Greece. On our last day, we explored Fira and Thira, I bought a handbag, and we took a cable car from the new port to the old port.
Then we boarded the ferry and were off to Crete!
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