Sunset Chasing in Santorini

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If traveling to Santorini to watch sunsets is cliche, just call me basic! And I’m not original when talking about sunset chasing here, it’s a honeymooner sport for sure and has been chronicled in numerous blogs and magazine articles. In my opinion, every sunset lover should come to Santorini to experience the sunsets along the caldera.   Yes the pictures are pretty, but you don’t realize the magnitude of the beauty until you are right there in the middle of it. It’s so much more spectacular in person! 

Happens every day, but still an awe inspiring experience!

The island is the stuff dreams are made of. Unimaginable dramatic cliffs, sparkling white architecture, a mystery of a sunken caldera that may have been the location for the lost city of Atlantis. It’s the superstar of the Greek Islands.


In typical hurried traveler, quick trip fashion, we only had a few days to spend on the island chasing sunsets. We checked out as many sunset locations as we could in a 3 day period. Yes, we went to 3 places 😉



We tend to enjoy a drink or five each night we are on vacation, but we also like to intersperse some healthy activities into our vacation binge drinking. The route to Oia sunset watching included a hike from Fira to Oia.


We decided on the Caldera hike we had heard about from Santorini Dave’s site, which was a wealth of information for our trip. If you are interested check out his post on the Fira to Oia Hike. After the hike, many waters, and then many beers, we made our way to dinner at Sunset Ammoudi Taverna, which a friend in Toronto had said was the most famous place to watch the sunset. We now know almost every place in Santorini is referred to as the “most famous place”, so just take the saying in stride when you hear yourself.


The restaurant is at the bottom of a hill and faces the Ammoudi bay. The view of the sunset includes picturesque floating sailboats docked in the distance. Having dinner with the sunset in the background is like dinner and a show, and yes, everyone around you will be taking pictures with their ipads as well.  Reservations can be hard to get around dusk so make sure you plan in advance.


Sunset Ammoudi Taverna

Ammoudi Bay, Oia 847 02, Greece

Santo Winery


Wherever we asked about sunset watching, this was the one place most everyone mentioned.  Some might think the setup is cheesy, and a little corporate. After all it is a large winery, perched on a caldera with the perfect scenery. I myself found it charming.  Santo Winery has a large tiered terrace with a number of tables available outside and inside with full view of the caldera.  Wine tastings (including the native Santorini Assyrtiko grape wine) and hordevours are available for purchase.  The sunset here offers a different perspective of the caulderra as its on a high perch a little more to the southwest.  It can get very busy during high season so make sure you have a reservation if you would like a prime spot for sunset watching.


Santo Winery

Pirgos Santorini

Any Hotel Room Facing the Caldera


Being that it might be our one and only time on the island, we splurged for a hotel along the caldera rim, and stayed at Mill Houses Elegant Suites. All of the rooms were positioned on the rim of the caldera, looking into the sea, with small patios you could use for relaxing and staring into the deep blue horizon. Daily breakfast was included in the cost (of course in Europe!), and you had your choice of having breakfast on your room deck, or poolside facing the caldera. The property had a small pool perfect for a dip in the afternoon heat.  What’s nice about viewing the sunset from your room, is you can order a bottle of wine from the bar (or if you picked one up from the local shop or winery), not have to deal with the crowds of tourists, and take your time with one of the most beautiful sceneries on earth.

Mill Houses Elegant Suites

Firostefani 84700, Santorini Island


Where’s your favorite place to watch the sunset on Santorini?

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