We had a fabulous 3 nights in Oia....John's accommodation made for the most spectacular setting....The view, jacuzzi and private deck were enjoyed daily. The accommodation was otherwise comfortable. We were able to access wifi intermittently though, which perhaps could be addressed just to make communication with distant family easier. The walk to the main walkway where the shops and restaurants are, is quite a hike, but great excercise, especially if one is indulging in the local cuisine and gelateau. I do however feel that a porter service from the shuttle needs to be provided on both arrival and departure. John organised this for our departure which was so appreciated. We arrived late, and really struggled to get our heavy luggage to the apartment without help on arrival...until having to make a plan ourselves. Not knowing what to anticipate exactly on arrival, I do think that a porter service should be automatically included under a surcharge if necessary.
We will definitely be back as Oia is magical!
We had questions re transport and John was very willing to help us organise transport. I feel that hiring a car is totally unnecessary. ...The local busses are cheap and frequent. People hire scooters and four wheel buggies, which would probably be fine, but after experiencing the local drivers, probably not the safest option.
If you are on the island for a very short time, we'd recommend staying put in Oia....it is a little piece of heaven!