I will start off by saying that this was by far one of the best hikes I have ever done, and I have done quite a few 3-5 hours hikes (hike of the gods on the Amalfi coast, etc.). I went on this hike with my parents, brother and my partner and it took us about 3.5 hours total, including time for the small breaks we took to enjoy the scenery and have our lunch that we brought with us. This hike features churches, walking through towns (Fira, Firostefani, Imerrovigli and Oia), Skaros rock, and breath taking views along the entire path. You could theoretically make a whole day out of walking to each town and exploring it individually instead of walking straight through like we did. For the hike: We started in Fira and hiked to Oia but you could definitely do it the other way. We just started there since that was where our cruise ship was docked. We initially got a little lost when trying to start the hike but discovered that we were just one block over from the signs that are posted along it. We asked a friendly local and they were chuckling to themselves as they pointed us one street down to where a clearly visible sign was. After that we were on our way! The first 1/5 of the hike is within the town of Fira as you make your way to Firostefani and since we started in the morning the sun was on the other side of the island casting the path in shade from the buildings. We were grateful for the shade since on the day we went there was only the slightest breeze and the weather gets quite hot! As we walked down the cobbled path through the streets of Fira, Skaros rock and the Town of Firostefani come into view in the distance. At this point the path breaks away from the buildings and for the rest of the walk you are more or less in the sun getting your tan and workout on. Once in Firostefani, you have a great close up view of Skaros Rock and there is no buildings in between you and the rock which is nice for photos. That being said, You can take a side path from the one you are on and hike up to the peak of Skaros Rock as well. It will add about 45 minutes to your hike. We opted not to do that since we were meeting up with the rest of our family later and did not want to make the hike too long. My partner and I in front of Skaros Rock (you can see the path you would walk along if you opted to hike up Skaros Rock as well). From there we continued the hike on our way to Imerovigli. This portion of the hike is more open and in the sun but you still have some luxurious hotels that you pass along the path with each room having their own clear blue water pools and beautiful vines with magenta flowers adorning the walls around them - they were a site all in themselves. A little tablet expressing the truth behind this island as we walked through Imerovigli (the town in the distance in Oia). My parents, my brother and I as we were walking along the town of Imerovigli. (Oia would be off to the far left in this photo if you followed along the island). As we went on our way from Imerovigli to Oia we stopped at one of the many lovely churches to have our lunch and take a bit of a break. There was a "washroom" here that you could use but make sure you are over there by yourself since it has no door and is more a pit in the ground. My brother did not have a problem with it though and thankfully I was sweating so much I didn't even need to go! The lovely church where we stopped to have lunch between Imerovigli and Oia. Now I am not going to lie, after this rest stop it gets a little tougher. The cobble stone path disappears and becomes sandy hot gravel that makes your feet boil in your shoes a little bit. There is also a mountain that you need to climb up and down to get around before you can hike your way on more hot sandy gravel and up another mountain before making the long relaxing descent into Oia. Bare in mind, this is also the part where you hit the middle of the day if you started in the mid-morning like us and the heat and sun are at their highest point. You have also been hiking for about 2.5 hours at this point. All this being said though, hang in there because the views are still amazing and it is completely worth it. This is on our climb up the second mountain just before we started to make the last descent to Oia (you can see Skaros Rock in the back). Panorama of our journey on the top of the second mountain (you can just make out the side of Skaros Rock beside Firostefani and we were walking even prior to that!) After that you make the final decent to Oia where you can get a refreshing beverage, go for a nice swim in Amoudi Bay, and feel accomplished and satisfied with the hike you did. The final descent to Oia. We did not end up going to Amoudi Bay ourselves since it is 300 steps down to the water from Oia and we had plans to meet with the rest of our family at Red beach back near Fira. What I really enjoyed about this hike was the scenery (of course) but also the fact that since the island is in a crescent shape, you can look back and see just how far you have walked along the way. It really puts it into perspective and you get to see the island from different angles at different parts of the day which adds to the hikes charm and already spectacular views. For you lovely people I have attached some tips below as well as a little document I made before going on the trip. It contains directions for the hike from another blogger (but unfortunately I did not save the actual website it was from) which really helped along the way. It also contains some brief overviews of other options when exploring Santorini that my family and I were keeping in mind aside form the hike. Thank you for sticking with me this whole time! I hope this can be helpful to you on your travels or help factor into your decisions for where to travel. Have a great one! Tips for the hike: 1. Make sure you have lots of sunscreen on as well as in your bag to reapply 2. Have at minimum 2 litres of water for each person - Trust me you will need it (don't worry if you don't start off with it, you can buy water and drinks throughout the 4 towns as you go but the stretches between are quite long so plan ahead!) 3. Wear really good hiking shoes - the parts of the path between Imerovigli and Oia that are rocky gravel in the sun will make them hot so they should be comfortable to avoid blisters (also it's a long hike and good footwear is essential) 4. Wear a hat! (or have one in your bag) - I did not wear mine initially (or for photos) but by the end I was grateful to have a break from the sun on my face 5. Have some money on you - you will need it for the taxi or bus fare to get back to Fira as well as your celebratory drink at the end of the hike 6. Bring a bathing suit if you want to enjoy Amoudi Bay at the end of the walk in Oia!