I had dreamt of those Azul rooftops with paralleled crystal waters for long enough that I knew that this trip could not possibly be actualized if Oai was steaming with ant farm tourists fresh off the boat.  So, at the risk of slightly unpredictable weather and cooler water, a pre-season visit to the island seemed like the solution.

Landing at sunset was enough to set the butterflies aflame, there is something about this island islands air that radiates a sense of calm! I did however make the amateur mistake when only spending a short time on an island and spent the bulk of my time within the hypothetical northern tourist walls (you wouldn’t go to Oahu and spend the entire trip in Waikiki)…  But alas, the southern points of Santorini are rich in history, authenticity, and sand filled beaches and albeit less cookie cutter tourist attractions.  Perhaps it is imperative to leave some resources untapped for a likening reason to return.

Sorting through your “must see/do” list is of course a personal decision, and I find in a small area, the timing of your arrival is of equal importance in guaranteeing a bit more pleasure!  I’ve seen my share of gorgeous vineyards from Napa to Marlborough and to be honest, 9 times out of 10 I would choose mezcal over vino.  So I skipped the vineyard tours , but if you do see your-self as a budding aficionado, there are several beautiful options.

STAY: 

Ikies, just outside of Oai, you beat the crowds in this corner sanctuary.

There are some beautiful AirBnB options in Finikia, which is a good location for a bit more solitude.

    EAT:

    Dimitris Ammoudi Taverna– their dolmades and fried red mullet are the best I’ve had and seated right on the water of Ammuodi bay.  This place was perfect for lunch, and there is a short trail just north of it that has a nice play to swim and cliff jump.

    Sunset – not too much of a surprise here… Book ahead so you will be dining at sunset (its actually right next to Dimitris).  You won’t regret getting the lobster pasta!

    Salty Bone– THE BEST MEAL I HAVE EVER HAD!!!  Unassuming location, but fresh beautiful fish and simple unique techniques, amazing chef and staff!

    Sunset in Ammoudi
    Salty Bone

    COFFEE: 

    Mes Amis, atop the cliffs overlooking the impressive Caldera

    Chilli, not to miss beach bar/restaurant if you’re in the southern part of Santorini

    Coffee Island, simple place, great coffee

    EXPLORE: 

    Sailing with Sunset Oai, will take you to all the best beaches on the island (its worth booking the afternoon option)

    Hike the Fira-Oai trail: we started in Oai and walked through Imerovigli, Firostefani, to Fira which is 6 1/2 miles.  Start early in the day, it can get very hot, so pack sunscreen and water, the view is worth it (we hadn’t planned on doing the whole hike, but was quite pleasant so we kept walking!  Had lunch in Fira and took a car back to our place.

    SWEAT:

    Maina gym, quaint, but with everything you need- free weights, cardio equipment and barbells.  Really nice and helpful staff.

    Zarkadas Ioannis Kai gym, Good sized, clean, and a lot of options with cardio, barbells, a platform, kettlebells and machines. Friendly staff.

    CHEERS: 

    For an intimate cocktail or meal, Fino

    For a cocktail with a view/vibe, PK Cocktail bar

    SHOP: 

    Oai is lined with shops selling beautiful linens and leather goods

    TREATS:

    Ice cream Lolitos in Oai, obligatory