We stayed in Oia for 6 nights at the place that John sublets on AirBnB. Oia is the densest, most beautiful, and thus most touristy of the towns on Santorini. We had a wonderful time exploring the island, and the crowds are easily avoidable with a little local knowledge (avoid the main path during the sunset migration).

John greeted us at the airport (for a reasonable upcharge) and took us to our apartment in Oia, which was very nice of him and also helpful because there are no clearly delineated addresses for the cave houses and I don't know how else we would have found it.

The apartments are nice, and have an unbelievable view of the Mediterranean. They are rustic and sparsely furnished cave houses with a limited supply of linens. These two cave houses are on the Caldera side of Oia and are really among the lowest down among the cave houses in the area (longer walk up and down, but almost no traffic). They do give you this wonderful feeling of being at the most relaxing edge of the world.

The place was tidy, but not clean because the ceramic walls and floor are a bit worn and produce clay dust. We decided not to have the tub/pool available to us, and were very happy with that decision. In apartment one the pool is inside and is a bit weird. The apartment was a bit musty despite the dehumidifier. I think that this is probably common among cave houses, but also exacerbated by the indoor pool. The kitchenette was nice to have for the minifridge, the sink, and wine glasses to enjoy inexpensive and delicious Santorini white wines, but was probably inadequate for cooking much more than pasta.

It is a quick walk up to the main section of Oia, where there are many amazing restaurants and bars (Roka was our favorite in Oia proper and the most authentic in Oia). The walk down to Ammoudi is well worth it for incredibly well-cooked seafood (Katina and Ammoudi fish tavern were the standouts here).