Exploring Greece: Oia, Santorini – Part 1

It took me a long time to decide on a destination for Jorge’s surprise 40th birthday trip in October. The main criteria: Must still be warm that time of year, must be relaxing, must be close enough to make the most of five days, must be near the ocean, must have good food, must have hotel with a pool. And for me, not much of the above really mattered, but it must be inspiring for photos.

Oia, Santorini, Greece by Stephanie Sadler, Little Observationist

Oia, Santorini, Greece by Stephanie Sadler, Little Observationist

Oia, Santorini, Greece by Stephanie Sadler, Little Observationist

Oia, Santorini, Greece by Stephanie Sadler, Little Observationist

Oia, Santorini, Greece by Stephanie Sadler, Little Observationist

And so, with the world at our fingertips, I eventually narrowed it down to Greece, and from there to an island, and from there to Santorini which was still busy enough mid-October for shops and restaurants to be open, but not so busy it was crowded with cruise ship crowds. Once I chose Santorini, I researched the island. Oia was the obvious choice for somewhere picturesque, quiet-but-not-too-quiet and with the opportunity to indulge in a little bit of luxury.

Oia, Santorini, Greece by Stephanie Sadler, Little Observationist

Oia, Santorini, Greece by Stephanie Sadler, Little Observationist

Oia, Santorini, Greece by Stephanie Sadler, Little Observationist

Oia, Santorini, Greece by Stephanie Sadler, Little Observationist

Oia, Santorini, Greece by Stephanie Sadler, Little Observationist

We were greeted in darkness late at night by the lovely staff at Oia Suites and shown to a beautiful room with a private hot tub on the terrace. The hotel has about eight rooms and is located just at the edge of the village.

Oia, Santorini, Greece by Stephanie Sadler, Little Observationist

Oia, Santorini, Greece by Stephanie Sadler, Little Observationist

Oia, Santorini, Greece by Stephanie Sadler, Little Observationist

Oia, Santorini, Greece by Stephanie Sadler, Little Observationist

Oia, Santorini, Greece by Stephanie Sadler, Little Observationist

Across the street is a wonderful family-run traditional Greek tavern with outdoor seating. It’s cheap and cheerful and the staff great you with your country’s flag for your table marker when you arrive. There’s live music every evening and on the first night we even got to witness some shouting of “Opa!” accompanied by some intentional plate smashing and subsequent cheers of the guests. It’s cheap and cheerful and friendly and we enjoyed the experience there so much that we went back two more times before we left.

Oia, Santorini, Greece by Stephanie Sadler, Little Observationist

Oia, Santorini, Greece by Stephanie Sadler, Little Observationist

Oia, Santorini, Greece by Stephanie Sadler, Little Observationist

Oia, Santorini, Greece by Stephanie Sadler, Little Observationist

Oia, Santorini, Greece by Stephanie Sadler, Little Observationist

Back in the room, Jorge realized that he had the whole bottle of complimentary champagne that they left us all to himself seeing as I’m pregnant. We settled in, excited to wake up in the morning and see what view awaited us. We weren’t disappointed.

Oia, Santorini, Greece by Stephanie Sadler, Little Observationist

Oia, Santorini, Greece by Stephanie Sadler, Little Observationist

Oia, Santorini, Greece by Stephanie Sadler, Little Observationist

Oia, Santorini, Greece by Stephanie Sadler, Little Observationist

Oia, Santorini, Greece by Stephanie Sadler, Little Observationist

Our breakfast was delivered to our terrace in the morning and, finally with the light of day, we stepped out for a better look. We had loungers overlooking the ocean, the volcano and the pool. The sun was already making its way over the island and we had no plans ahead but to go out and explore, eat Greek food and enjoy a swim and some sunshine.

Oia, Santorini, Greece by Stephanie Sadler, Little Observationist

Oia, Santorini, Greece by Stephanie Sadler, Little Observationist

Oia, Santorini, Greece by Stephanie Sadler, Little Observationist

Oia, Santorini, Greece by Stephanie Sadler, Little Observationist

Oia, Santorini, Greece by Stephanie Sadler, Little Observationist

Oia (pronounced “ee-ah”) is a small village with one main pedestrianized pathway to follow. The views are stunning. I stopped every few steps to take it all in and snap some photos. Everything whitewashed with accents of blue paint and the occasional green cacti, all with a constant view of the ocean and the drop of the caldera below.

Oia, Santorini, Greece by Stephanie Sadler, Little Observationist

Oia, Santorini, Greece by Stephanie Sadler, Little Observationist

Oia, Santorini, Greece by Stephanie Sadler, Little Observationist

Oia, Santorini, Greece by Stephanie Sadler, Little Observationist

But more on the actual village and how we spent our days next week!

22 thoughts on “Exploring Greece: Oia, Santorini – Part 1”

    1. I’d definitely recommend it. This was my first trip to the islands, but I’ve also been to Athens a few times and olive picking in Kardamyli. Every visit to this country has been unforgettable. It’s one of my favourite places.

  1. These pictures are unbelievable! They capture the beauty of the island so well. I am dying to go to Greece and these pictures just push my dream even more over the edge!

  2. Pingback: Exploring Greece: Oia, Santorini - Part 2 - Little Observationist

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