We reached our last destination by way of ferry and met by its jaw-dropping cliffs. Because our trip was entirely last minute we didn't have much time to plan our accommodations and forgot to downsize our suitcase situation.. (in our defense we only thought we’d be traveling to Texas and Portland). After being dropped off in a random parking lot, a small man greeted us and our baggage. We were all equally concerned for the journey ahead. 

Wandering through the narrowing cobblestone pathways of Oia, we received embarrassing glances, laughs and stares along the way. After the trek when we could no longer walk any further, we were advised, “This is the hard part !” and we soon saw why. Our room was located at the very bottom level, essentially a ninety-degree angle of stairs winding all the way down. Lets just say maneuvering up and down was quite a challenge and not recommended after a few glasses of ouzo. The reward: an ethereal view. We were instantly transported to our own little traditional cave home, it was so quiet and peaceful.

With not much to do besides lazily sit back, relax and enjoy the view, Santorini is a slow-paced island where you have to consciously remember to be in the moment. I easily found myself behind the camera, wanting to snap a photo every step I took. The most adrenaline-filled moment took place when we experienced a fish pedicure. An experience very hard to describe but put simply, feels like dunking your toes into a bunch of little jacuzzi jets.

For dinner, we journeyed down the famous Thousand Steps to Sunset Amoudi Fish Tavern. Fresh seafood restaurants lined Amoudi Bay and the translucent water was lit up by the all the lights like a scene from a movie. I will admit to calling a taxi on the way back because after stuffing ourselves full of food the hike back up seemed less than achievable.

The following day, we wanted to see if any hotels had availability because we wanted to get a different feel on our last night (staying in an airbnb is a great way to see the traditional side of Oia, but when trying to get transportation it can be difficult - so arrange accordingly and make sure you have enough cash upon arrival). We had almost lost hope, as every hotel was at full occupancy until we found Santorini Secret Boutique Hotel. The only room left was the infinity suite… soo convenient. I don’t know what we would’ve done without the help of the two gracious employees who carried our bags from one end of the town to our new hotel on the opposite side but they were our definition of Greek Gods. 

Never in my wildest dreams could I imagine a more stunning room. The entire space was built into the volcanic rock with unobstructed views of the caldera and our own private infinity edge pool. 

Of all the delicious food we had in Greece, the most memorable meal included a Santorini salad at Thalami, move over Greek salad, layers of cucumber, tomato, red onion, green pepper, Kalamata olives, and caper berries and leaves are sprinkled with soft feta cheese and oregano, then drizzled with lemon juice and olive oil. The fresh vegetables in Greece were so incredibly sweet, they tasted like candy. The special iced coffees known as 'frappes' are also a must. 

We made a reservation at Ambrosia for dinner one night, accurately named the most romantic restaurant on the island. Brooke and I had a nice little date on top of the world as we devoured seafood pasta drizzled with truffle oil and grilled octopus with a fava bean mash to die for. Every night tourists line the walls of the small castle at the end of the main path to watch the sun sink beneath the horizon. This spot gives way to the best view in Oia, for the picture perfect sunset, something the island is known for.


Hit List


Santorini Secret Boutique Hotel



Amoudi Bay, Red Beach


Kissingfish, Oia Castle at Sunset, Roof Garden at 1800, Atlantis Bookshop - best bookshop in the world according to National Geographic. Santo Winery


Sunset Amoudi Fish Tavern, Santorini Salad at Thalami, Lolita's Gelato, Ambrosia, Pitogyros, Catch Bar