When considering staying in Oia, beware the cruise ship crowds which can overwhelm the place almost every day. This, on top of the day trippers, can make the place hard to walk in the narrow main walkway that runs through the 'village' Oia doesn't really represent the true culture of Greece and feels like the Disney version of a Greece village. What saves it of course, are the stunning views of the Caldera and the (unremarkable) volcano.

 Oia has its own dedicated set of visitors, who know what’s different about it and appreciate these fine differences. In this part of the Santorini island you can see a lot of architectural innovation.

 The residential complexes of Oia were declared an architectural monument in 1976. Oia is divided into two parts by the central Nomikos Street. The side facing the Caldera and the cliff holds ancient ship crew members’ houses. These are carved right into the volcanic rocks, and are called the yposkafa. The other side of the road contains the so called “captain’s homes” (kapetanospita), built for the middle-class members of the society, usually ship owners. You can check out afternoon tours by providers like Baikas Travel.

 If a little sea action is something you prefer, you can try spending some of your holiday on a boat. Here you can soak in Greek architecture and the Caldera from a boat on the azure Aegan waters. There are many companies out of Santorini that offer boat rentals that allow you to travel around the islands at your own pace. Several platforms offer boat rentals from verified Greek charter companies like Zizoo, Alphayachting, and SailGreece. You can also get a skipper if you have no sailing experience.