top of page
  • Writer's pictureAnna Jacobs

5 Days in Oai, Santorini

After 27 hours of travel, I landed in Oia, Santorini to soak up the sun and the sights for 5 days. Before I dive into my time in Oia, a quick note about how I purchased flights to get there. Traveling from the United States, and Google flights were showing me ticket prices from Redmond, Oregon to Santorini at astronomical rates. I used sites like which brought me to and, both of which had more reasonably priced airfare. 

Oia is expensive in terms of accommodations and food, but if you want to be in the heart of Santorini, it really is the place to be. We found a charming Airbnb called The Captain's House, it was just steps away from the main street and the Caldera. If you want to stay on the Caldera, with those iconic views, you'll most likely have to stay in a hotel. 

We traveled to Oia during the end of their busy season, the beginning of September. In the morning, grabbing breakfast on the main street, the town was quiet, starting around 10AM the tour buses and cruise ships began to descend on Oia. From this point on, the streets were so packed in places, it was difficult to walk; stopping to browse shop windows, or take a photo is nearly impossible unless you want to cause a traffic jam. To avoid the hoards of people, I woke up for sunrise almost every morning, walked to the Byzantine Castle ruins (the classic view point) to enjoy the sunrise, and then wandered around the quiet streets. Of course the shops aren't open at this hour, but the serene atmosphere feels like a more authentic way to experience Oia, and then you can wander down random streets and stop to enjoy the bougainvillea. If you are itching to catch a sunset at the ruins, you'll need to show up at least an hour early to claim your viewing spot!

One day we took part in a five hour sailboat tour around the islands, with Sunset Oia. It was a beautiful way to see the Caldera, as well as the popular but packed Red Beach and White Beach. We stopped to snorkel and swim, had a BBQ on the boat and pulled off at the Hot Springs for a dip. We dropped anchor just before docking to watch the sunset on the horizon. 

For as dry as the island of Santorini is, there are a plethora of wine vineyards. We were told that we had to do a wine tour, but we aren't really a 'tour bus' type, so I did some research and we settled on Boutari. Boutari Winery is the oldest winery on the island of Santorini, after our wine tasting they gave us a tour of the wine cellar where they store their wooden and stainless steel casks and produce their wine. They then brought us out to the vineyards to explain their technique for working in such an arid climate. The vines grow low and weave into a basket shape in order to keep the plants low to the ground and prevent them from being scorched by the sun. 

To escape the rush of Oia, we rented a car and drove the island one day, for some beach time, map yourself to Chilli Bar Restaurant and enjoy the comfy chairs, soft sand, and crashing of the waves.

Take Aways: 

- Get up for sunrise to avoid the crowds at the ruins

- For a night out, go to Catch for dinner, the food is amazing! 

- If you want to stay in the Caldera, you'll want to look at hotels

- If you're a photographer, be sure to bring a telescope lens

- Eat as many gyros as you can and order fresh juice!

25 views0 comments

Recent Posts

See All


bottom of page