I extended a business trip for a quick vacation in Santorini with my wife. I did very little research ahead of time so I didn't know really what to expect. Being that it is winter and off season for most vacationers, Oia felt like a ghost town when we arrived. At first I was a little disappointed because pretty much no business or restaurants were open, however my opinion shifted quickly as I realize what the little village truly had to offer. The scenery was gorgeous and it's really not an exaggeration that the little private porch outside the cavehouse is one of the best spots to take in view. We spent a lot of time sitting on the chairs watching the sunrises and sunsets. We walked around a lot and extensively explored all the alley ways and scenic spots. It was incredibly eerie to walk around and not see anyone else on the streets for an hour. This, however, made the trip all the more special. It was so quiet and serene, there were no other annoying tourists and no one else to spoil the view or get in our pictures. We befriended a few of the stray cats near the apartment, especially a tri-colored cat tagged with "161" in her ear! One morning we watched the sunrise with Amelia the street dog who was curled up on the lounge chair outside when we awoke. For food, there were a few local markets that were open to buy groceries. We had coffee one morning at the cafe in the square, there were a lot of local men smoking inside and we didn't feel so welcome there. We prefered another bakery patisserie on the main path (Nik. Nomikou) called ΠΑΣΣΑΡΗΣ, they had amazing baklava. For dinner we ate twice at Alkiona Restaurant a short walk back down the main road; It was delicious and very authentic with a friendly atmosphere.
Despite being cold outside, the cavehouse felt was warm and cozy, there was a space heater that we used a bit for added warmth. We cooked breakfast in the kitchen, a little cramped, but had everything we needed. The bathroom was good and hot water for the shower. It was a really unique experience to be in a cavehouse like this. After walking around the village and exploring some of the very high end resorts, I can't see it being worth it to spend the extra money compared to this experience.
Jackie and Nikos were perfect hosts, very friendly and excellent communication. They arranged transportation for us on arrival and departure which helped us just enjoy they island and worry less about the logistics. I would stay here again in a heartbeat and recommend it to anyone else planning a visit here in the future.