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Santorini, Greece :: Sunsets, Wine-Tasting, and a Dream Come True

You have Sisterhood of the Traveling Pants to thank for this post. 

Sisterhood of the Traveling Pants (very easily) convinced a bucket-list-obsessed middle-schooler Caroline to scribble and underline "see sunset in Santorini" at the tippy top of a list containing meaningful, ambitious goals such as "eat french fries with Kate Middleton" and "own a private jet" and "do my laundry" and oh wait, it looks like I'm mixing up my lists.

All of that is to say, as sad as it was to bid doviđenja to Dubrovnik and our new friends, the prospect of finallllllly, finally, finally getting to see the land of blue rooftops and famous sunsets was equally exciting. 

Well... it was until we realized that getting to that mystical land involved 10 hours in the Belgrade airport, a 3am layover in the Athens airport where we ravenously succumbed to the powers of a McDonald's breakfast, and a 6:45am touchdown in Santorini, where at least we were welcomed by a peaceful sunrise.
Please excuse the haggardness.

Not only had we spent close to 20 hours on the road, BUT ALSO our room in the quiet little village of Imerovigli was not available for another 7 hours.


So we did what all delirious folks might do, which was to hop on a very overwhelming, very confusing bus (where do we wait? how do we pay? is this the right bus? where do we sit? is this our stop? It's all Greek to me, sir!!) to Thira, find a cafe with free WiFi and some spanakopita, book our return flight to Athens, and then slip into a fish spa.
Again with the haggardness. Please forgive.

Afterwards, we sauntered through the streets, checking out souvenir shops and darting through whichever street looked the least crowded and most shady. Even as exhausted as we were, I had this dopey grin on my face as I breathed in the Mediterranean air, jolly folk music all around us. "You must really like it here," Cassandra said, a blink away from passing out right on the cobblestone.
Our first of a trillion gyros in Greece! Hardly exaggerating at all.

At long last, it came time for sweet, sweet relief and we settled into our lovely Airbnb for a snappy rest. Real snappy because 10 seconds after dropping off our luggage, we convinced ourselves that hey, sleep can wait. Let's go see ourselves some Imerovigli.
Seeing those white houses perched on the hills brought about butterflies in my belly–the kind that inevitably shows up when dreams come true. I couldn't stand how beautiful Santorini is, how it's exactly like I imagined. Zig-zagging paths, an expanse of sea so wide and so blue and so still, mountainous volcanoes stretching in all directions.

But it was also everything I didn't expect. Bigger. More dispersed. Less pristine. Wonderful beyond imagination.
As we noticed the sun inching lower, Cassandra and I quickly chose a bar with a view of the Caldera. Accepting that it would probably be overpriced and underwhelming, we nevertheless beelined it for the last 'front-row seats,' ordered a Vinsanto and a fruity cocktail and some peanuts, and waited patiently.
Cassandra pulled out her trusty notebook and started flipping through it, reading beloved memories from our past weeks and months aloud.

We laughed at our travel mishaps.

Wondered about what our friends were up to.

Discussed all that we'd learned in Croatia, in Bosnia.

Shared how much we already missed our Stanford, dearly.

Philosophized about fortune and privilege. Pure luck. It's what we felt in that moment. Pure, stinkin' luck, because how else could it be that right here, right now, we were the ones who had the opportunity to sit at this cliffside bar, sipping expensive drinks, taking in a sunset that I had longed for years and years to witness?
... ever so faithfully, the bright orb settled into the horizon.

All of us in that bar quietened, absorbing the still-pink, still-yellow hues of the warm sky and the placid sea – like the thin film atop freshly heated milk. Then, the clapping bursted and a young boy laughed in glee and we were stirred from being absolutely spellbound.
On our way back to our Airbnb, we stopped for dinner at Avocado, which came highly recommended by our host. And I mean, with a name like that, who could refuse?

They started us off with ricotta cheese and shots of rakija on the house.
Then a rich, hearty moussaka and a delicious Greek burger with a half-liter of red wine to share.

I mean, we had to. The "half-liter" thing we could only get away with in Europe, and so we had to take advantage!
With a side of glittering Oia off in the distance!

If you ever find yourself in quiet Imerovigli, rest assured that Avocado is the way to go for a scrumptious dinner.
The next morning, we woke ourselves bright and early for a wine-tasting tour.

Our tour guide fetched us from Imerovigli and drove us to the highest point of the island where the vineyards are. He pointed out the low, bush-like vines that hugged the ground due to the salty winds. And, then! It was off to taste some wine! 
Our crew of two couples and two pairs of best friends.

We were poured glass after glass generously, and taught to sample olives and tomatoes and charcuterie and crusty breads with each. And each time we thought for sure this was the last of the wine, our sommelier came 'round the table and topped the glasses up once more.
Come, there's more! He beckoned, and we followed.

To another winery, this time under the beaming, full-force sun.
And then to a brewery, where because we were running late, we all basically had to chug our beers.

Finally, to one last winery!

This was the one that did us in.
While the couples on the tour opted for a cooking class that took place off in a corner, the two pairs of best friends were left by our lonesome with a platter of small bites and copious bottles of wine.

Our tour guide stopped by intermittently to make sure that our glasses were full of Vinsanto (a candy-sweet wine produced only in Santorini) and our friends The Couples would drop by to sneak us some of their newly learned masterpieces, and the four of us chatted travels and Canada (where they're from) and the US (where we're from) and Greece (because, hello).
Before we knew it, the wine had gone straight to our heads and our limbs and our bellies, and the driver directed us into the van with a, "okay and now we'll take the scenic route to Oia!"

So, um. By "scenic" he also meant the curviest, windiest road which he SPED through and while yes it was gorgeous and breathtaking and scenic, the drive did not rest well with Cassandra's motion sickness and just as we pulled into the parking lot of Oia, puke streamed down her dress, hands, and the van. Let's just say... she still, to this day, as an aversion to dessert wine.

Apologies for the visual, but it made quite the story for us to tell. 

Needless to say, we sheepishly headed back to our place in Imerovigli, freshened up, took a much needed snooze, and then dragged ourselves back to the bus to be in Oia in time for the sunset. Because I don't care how terribly hungover I am, there is no. freaking. way. I will miss seeing the Oia sunset. Just no.
And while I am beyond grateful that we managed to whip ourselves into shape in time to see this stunner, I will say that the one word to describe an Oia sunset is: crowded. As heck. Though the sunset was fiery and picturesque and still a dream come true, the fanny packs and selfie sticks and sweaty bodies and tall dads blocking the view certainly chipped away at the magic.

My recommendation: let the Santorini sunset take your breath away in a quieter village, like Imerovigli or perhaps even Thira although I'm sure that one's quite popular as well.
To avoid getting lost in a sea of people, Cassandra and I waited out the crowd by first, hiding away in the balcony of a little dessert shop in the middle of Oia where we shared cake and gazed out into the darkened sky, lit up by the stars and glowing swimming pools.

For sure another moment to remember.

Second, we followed our noses to another gyro shop and fulfilled our desires of midnight gyros stuffed with lots of french fries and tzatziki while we waited for the bus. For future reference, the best gyros in Santorini we think is the one we tried here–Pitogyros–right in the alleyway across from the Oia bus station. You can't miss it. Another pro tip - we heard that the ice cream store Lolita's Gelato should not be passed up.
For our last morning on the island, Cassandra and I trekked back to Thira to revisit a few of the jewelry stores that had caught our eyes.

We spent quite some time picking out presents for people back home, as well as for ourselves. (The Bead Shop was our favorite stop – so many intricate, unique pieces of jewelry that is incredibly affordable, plus there's always the option of making your own. Bonus: this is right next to the fish spa that we went to!)
Of course, we managed to fit in one more round of gyros!

Before jetting off from the Santorini airport back to Athens. I've got to give it to Santorini – for a place renowned for its beauty and peace, its airport sure was the most "sardines in a can" kind of airport I've ever been to. Complete chaos, but it got the job done.
So there we have it! Santorini! Likely the most anticipated travel destination of mine. I will confess that I do think we didn't adequately give Santorini the chance it deserved: we booked our Airbnb super late in the game (although in hindsight, staying in Imerovigli was probably one of my favorite parts of our visit), were absolutely exhausted and travel-fatigued, didn't do our research, and should've explored more of Oia in particular (we didn't even see a donkey! or a beach!)...

But there's always next time, right?

New addition to the bucket list: see Santorini sunset. Again.


  1. OMG! These pictures are so beautiful they look fake! Also those gyros, dang. That's all I would eat if I was there too! I stayed with a family in Italy who owned a seafood restaurant and I refused to eat anything else (except pasta) the whole time I was there.

    1. Greece itself was so beautiful that it didn't seem real! And yes, the gyros were so amazing. Except, the best ones were still to come (in Athens)!

  2. Beautiful photos. Looks like a great time. And, I love gyros, so good!

  3. It seriously sounds like you guys had a great trip. Greece is one of the top countries I'd love to visit and seeing these images makes me so jelly! :3 And yes, Sisterhood of the Traveling Pants inspired me as well, haha.

    1. Worth all the hype. Such a breathtaking place, although next time I most definitely want to explore more!

  4. Oh my goodness, you must have been so exhausted! I think I'd have done the same and passed up sleep for a few more hours just to explore the place a little more :) xxx
    Lucy @ La Lingua | Food, Travel, Italy

    1. Ha, there was no chance I was going to miss seeing any of Santorini to sleep. Possibly the ONLY thing on this planet I wouldn't give up for sleep!!

  5. Love the Traveling Pants!! I'm dying to go to Santorini for the exact same reasons!! That sunset though.... I definitely need to experience that! The streets look so cute and quaint! Yes, Santorini needs to be on my list!

  6. I adore travel posts . . . I have such wanderlust so I love to see where others are vacationing! What an amazing trip and memories for a lifetime! Yay you!

  7. Santorini is at the top of my bucket list.


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xx Caroline