This is a strenuous walk, especially traveling Oia to Fira, as Fira's higher altitude makes for more up than down hill. We did do a lot of both, however.
In the early Aug heat, we set out from almost the northernmost tip of Oia at 6:45 am and arrived at the bus stop in Fira about 10 km (almost 6 miles) and 3 hours later, stopping only for rest, water and photo breaks. The exercise is excellent and the scenery magnificent, especially where you have the sea on both sides.
We found that good footwear and a sun hat, sunscreen, and sunglasses were the most important items to have, and stress the importance of relatively thick soles as the cobbles and uneven rocks for much of the journey were quite tough on the feet. Hiking boots are definitely not necessary (too heavy), but runners with thicker soles and decent tread for traction are appropriate. This is followed by water. We drank 500 ml of water each and found this adequate. You can rehydrate with purchased water or other beverages at the end.
The Oia to Fira direction is best if you start early in the morning or go late in the afternoon when the sun will not be in your face. Otherwise, if you are staying in Fira I think the other direction may be preferable as it is more downhill overall.
If you go Oia to Fira, at about the halfway point (I think it is the San Antonio resort where the bus stops) you will come to a fork on the lower part of a big hill, and you will have to decide whether to skirt around the left side of the hill or take the steep graveled path to the right. We took the latter and although it is only a little bit shorter and the initial climb is hard slogging on loose gravel, we're glad we did. First, it was not adjacent to the road but around the back of the hill and second, we avoided the sun which would have been beating down on us on the path to the hill's left side.
What we noted, in addition to the sense of accomplishment on completion, was the variety of plant life, the many lizards and butterflies, the long lines of marching ants, the lava stones, the lichen-covered rock, the cooling breeze, the rock formations and caves carved out by erosion, the many churches adjacent to the path, and the sound of the waves crashing on the cliffs below. And we marvelled at the fact that many people and likely donkeys hauled cement up there to make this rock path for us all.
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