A couple of years ago, I was flipping through a travel magazine when I stumbled upon pictures of pristine white buildings crowned with startling blue domes, set against an azure sky.

At first, I wondered if it was a painting. It looked too beautiful to be real—more like a work of art suspended somewhere between dream and imagination.
But if it was real, I needed to know: Where is this place?
Sure enough, the magazine revealed the location: Santorini. Oia, to be exact.
And just like that, a seed of wanderlust was planted.
Being a hodophile with an insatiable case of wanderlust, I immediately began planning my trip to Greece, with Oia on the must-visit list.
And let me tell you—it did not disappoint.

I decided to visit in April—my birth month. The weather was just right: warm but not scorching, and the crowds far thinner than during the peak summer season.
Because it was just before tourist season, I got a firsthand glimpse into why Santorini always looks so impossibly pristine in photos. Everywhere I went, hoteliers and homeowners were busy painting, whitewashing walls and steps, and polishing windows to perfection.
I stayed in a charming boutique Airbnb—Seven Suites—complete with a whirlpool and infinity pool just outside my bedroom.
Whether under a canopy of stars at night or in the quiet hush of dawn as sunlight pierced the horizon, I took advantage of the pool, gazing into the distance, lost in wonder.



My exploration began in the village of Imerovigli, where whitewashed homes cling dramatically to the edge of a 400-meter (1,312-foot) caldera on the western side of this semi-circular volcanic island.


From Imeroglivi I trekked to Fira (or Thira), the capital, winding my way through narrow, zigzagging footpaths, passing those iconic spots that many an ecstatic tourist, like myself, captured in photos and posted with hashtags galore.
But there was one photo I wanted above all else:
A flying dress photo.
Clad in a glamorous dress with a feather-light train made for the perfect windblown effect, I climbed stairs, scaled rooftops, and challenged my fear of heights in pursuit of the shot.
Every step upward came with a little self-talk:
“It’s okay.”
“You’re okay.”
“Don’t look down.”
“Think of how stunning these pictures will be!”
And somehow—miraculously—I made it to the rooftop and got a few shots I absolutely loved.

After conquering a rooftop, though, you just gotta get a blue dome shot:


With only three days on the island before my Greek Isles cruise began, I finally made my way to Oia—the place that had lived in my imagination for so long.
And she did not disappoint.
Oia, Santorini’s postcard-perfect village, is often considered the island’s most picturesque destination, known for its whitewashed beauty, iconic blue domes, and breathtaking sunsets.
The windmills.
The remains of an old Venetian castle.
The sweeping caldera views.
This is what wanderlust fulfilled looks like.



From the village, beginning near the Venetian castle, I trekked down nearly 300 steps—278 to be exact—to Ammoudi Bay.



I descended on foot, but you could rent donkeys. Already challenging my fear of heights by just looking down from the castle to the bay, I decided against going down on the back of an ass (pun intended).
Ammoudi Bay is stunning—a tiny cove with crystalline waters and fishing boats bobbing gently in the sea. Undeniably one of the most picturesque corners of Santorini.
Along the waterfront, fish taverns line the shore, offering fresh seafood and front-row seats to the rhythmic soundtrack of waves meeting the Aegean Sea.
And yes, I fully leaned into the experience at Sunset Ammoudi, a restaurant renowned for its exceptional seafood and unforgettable setting.








There may not be beaches at Ammoudi Bay, but that certainly did not stop me from getting into the water. Well… not fully.
At the very least, I had to dip my feet into the cool, crystal-clear waters of the Aegean Sea.

And of course, what’s a trip to Santorini without fully embracing those iconic white buildings and blue domes?








And last, but by no means least—Greek cuisine.
As someone who loves good food, Santorini fed both my appetite and my soul.






In a heartbeat!!
That is my resounding response to: Would you go back to Santorini?
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All photos taken by me!
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In creative solidarity, Dee
Thank you Leo. Appreciate you stopping by. Cheers
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Awesome pics
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Thanks!!!
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Yay!! I’m so glad you enjoyed your Santorini trip, and your flying dress pics are perfect!! 👌😊 I was in Santorini recently myself, I’ll posting more about it soon. Sounds like April is a good choice to avoid the hot sun and crowds, June was scorching hot. I didn’t spend much time in Oia, but did do the hike from Firostefani to Oia.
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Hey Cheryl. Yes the weather was wonderful in April and we weren’t bombarded with crowds. I too wanted to do that hike but didn’t get around to it. Looking forward to reading your Santorini article. Cheers
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I’m not seeing my comments show up for some reason, but here’s another one: you are gorgeous in your red and orange dresses! I need a packing list consult, Goddess 😍💙
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Hey Natalie. Most def … would love to give you tips. You will absolutely-tutely enjoy this trip.
Thanks for the compliment 😍💕😍
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Stunning! Saving this as I plan my fall trip to Greece 🇬🇷. Thank you, Dawn 💙
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Yipppeee !!!!! You’re going to LOVE it!!!! Can’t wait to see your pix. I know they’ll be stunning!!!!
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Your photos are wonderful! 🌺🩷
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Hey Kymber. Thank you!!!
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I enjoyed seeing your stunning photos of Santorini, Dawn! And you in that dress…simply gorgeous. Thanks for sharing!
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Hey there Lynn. So happy you enjoyed the pix. Good to see you here again!! Thanks for stopping by!
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My pleasure!
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I absolutely loved it – except for getting COVID at the end of the trip.
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Yikes. That must have been a bomber. it was at the end so you were able to enjoy your trip. Hope you’ve fully recovered.
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It actually was quick and minimal. The only time I had the bug.
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Thank God!!!! Stay well
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Stunning photos, Dawn! Breathtaking in the red flowing dress. ❤️ Lovely to read of your dream-come-true journey!
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Thanks Michele!!!!
Have a great week ahead!!!! ❤️💐❤️
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A pleasure! Thank you and you too. 💖
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Thanks deary!!!
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Your pictures are stunning! What a great shot with you in the red dress that looks like it’s floating in the air. We haven’t been to Greece yet. But it’s on the list! It looks so picturesque.
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Look at you, Girl! You’re stunning. I went to Greece last year. It’ pretty amazing, isn’t it?
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Oh you did?! What did you think of Greece? Yes i found it amazing!!!!!🤩
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I’m glad you were able to reach Santorini and your dreams Dawn. The photos are wonderful, especially the white buildings and your flowing dress!
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Yup no feeling like your body arriving in a place where your heart already was!!!
Thanks Brad!!!!
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Goddess, wow! What amazing photos. What a place. Now I’ve seen it all. Wonderful. Thanks for sharing these with me. Xoxo
Beautiful dress shot. Adorable. Love it Dawn. Bless.
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Wow, living life to the utmost! Thanks for sharing the gorgeous photos of your trip. Sooo beautiful!
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Truly a dream come true. Glad you enjoyed Eliza!!!
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Wow those pics are breathtakingly beautiful! I will have to add Santorini to my bucket list.
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Oh you must. You’ll not be disappointed!!!
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Gorgeous photos! Greece is own your list and you are the second person posting photos of Santorini this week, sigh 🙂
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Oh ok looks like the signs are compelling for you to move it from your list and check it done ✅ you’ll love it!!!
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