I had trouble posting yesterday so posting Day 14 & 15 today!
Oia
Today was a spectacular day of walking. The Caldera hiking trail from Fira to Oia sounds great in theory but I have no idea how people do it in the summertime, or any even after 9 am even in October! With the sun beating down on you and zero shade anywhere, it feels way hotter than the temperature says. That and the humidity, I don't get how people venture this climb at all!
Instead of doing the hike, we took the hotel car service to Oia to walk around. It's tiring just walking in the city! With all the steps up and down and also with no shade.
Stair master city
I love Oia more than Fira. Oia was more scenic and had more pathways to walk around and explore on. We spent about 4 hours (including lunch at Skala, which was very good and beautiful views) walking around and taking it all in. Aim to get near Ammoudi Bay, and then you know you've seen most of it. It's about 200+ steps down to the bay so we didn't go (didn't want to climb back up!) but there's supposed to be good seafood taverns there and an area to swim in.
Ammoudi Bay
After Oia we went back to Fira to explore it some more as well but we were done in two hours. After we went back to the hotel and rested, we watched the sunset from our hotel which was gorgeous and different from the night before since there were some clouds.
We then raced against the fading light to dinner up in Imerovigli. We barely made it, it got dark fast and the way up from the hotel it is not an easy walk. A flashlight is recommended as there are some parts of the trail that are well lit be others not so much. Also, although it's generally pretty safe in Santorini, best not to walk this alone since it's so dark and you need to be careful since the path can be rocky/not even/has steps. We ate somewhere not worth recommending and then went for a stroll all the way down to Fira. Walking along the rim of the island at night was also wonderful. It took us about twenty minutes to walk thru Imerovigli to Firastefani and then finally to Fira (think this walk was about a mile total). It was a different experience to see the villages at night. From Fira to Oia, it's about 5 miles. From Santorini Princess Spa to the center of Imerovigli, it's about a mile (due to the uphill climb). From Imerovigli to Fira it's about a mile.
Down to Fira
The northwest side of the island, Firastefani and Imerovigli
Cruise ships in the Caldera