Beginner’s Trail Guide: Hiking the Caldera in Santorini

When you think Greek islands, you think Santorini. Your next thought may be white houses, cliffs, sunsets…but hiking? Yeah, hiking didn’t come to mind when we first decided to go to the Greek islands for our honeymoon, either, but I was really excited to find out there are some really spectacular trails.

Santorini’s Caldera Path was a hiking highlight for us, with six miles of ridiculous views, cool villages and towns, and a giant nutella crepe waiting for me at the end. If this is the only walking you do on Santorini, I would highly recommend our tour guide Nikos Boutsinis.

We took a walking tour with Nikos the day before hiking the Caldera, opting for Nikos’ Santorini Wanderlust tour that took you through the town of Pyrgos to talk about Santorini’s history, architecture, and culture. We not only had so much more historical context to do the Oia to Fira hike, but also got some local intel from Nikos on the best way to do it. Namely, don’t start in Oia!

We followed Nikos’ advice to hike the Caldera from Fira to Oia since we were staying in Oia. This was (unsurprisingly) spot on because we were BEAT after the hike and I can’t imagine having to then wait for a bus, pack on with other sweaty people, do the 15-minute drive back to Oia, and then walk back to our hotel room. I would have just asked Billy to leave me at the bus stop to die.

Since Fira is also the southern end of the path, and you hike northwest from there, the sun is at your back instead of blasting you in the face. Santorini is really effing hot, so that made a huge difference, as did starting as early as possible. We took the first bus to Fira at 7:30 a.m.

FYI all the school-aged kids also take the first bus to Fira at 7:30 a.m. and the bus driver gives zero effs about “safety” or “how many people can actually fit on this bus.” Be prepared to become intimately familiar with random teenagers and your fellow tourist passengers.

We envisioned a peaceful ride, sitting in the comfy charter bus seat, applying sunscreen like we’d had on all the other buses we’d taken on the islands. No. This was the opposite. But the bus was dirt cheap so we couldn’t complain too much.

Neither of us can read Greek, but as far as we could tell, there were no signs pointing you toward the Caldera path. We just headed uphill from the bus stop, toward the coastline. Overall, signage is not great but as long as you follow the path closest to the water on your left, you’ll be fine.

The Caldera path winds its way through Fira, Firostefani, Imerovigli, and ultimately Oia in addition to plenty of pretty countryside. The views the entire time are stunning, and it’s nice to pass through towns for a bathroom break, more water, and at least one Snickers ice cream bar.

But let’s be real, six miles is a long ass way to walk. So is it beginner-friendly?

I had done almost zero physical activity for the month prior to our honeymoon, unless you count dancing my pants off at the wedding. I do walk around my neighborhood a lot and bike to work about three times a week, so I like to think I had a good baseline. I also was really excited about the hike, even though I knew it was going to be hard.

And it was. The beginning of the walk had been pretty flat, with a bunch of shade mixed in with scenic views. But there are two really steep stretches later on, and to be totally honest I was pretty over it at the second gigantic hill. I was SO HOT and getting grumpy because I was struggling.

But then we got to this view and I remembered why I wanted to do this. Santorini is unique; the famous caldera (or cauldron) was formed because of a gigantic volcanic explosion, when much of the island sank under the weight of all the ash. What was left behind are dramatic cliffs around a crescent-shaped bay, and it was one of the coolest things I’ve ever seen. Yes, you’ll be tired, you’ll be hot, but you’ll never regret this hike. It’s amazing.

Plus, right around the poing where you’re like, “Okay these views are cool but I CANNOT go uphill any longer,” there’s a church. Aka a place to sit. IN THE SHADE. We had plenty of company in other sweaty, exhausted people which reassured me that I wasn’t the “only one” having a hard time with this. After a few more minutes, my spirits had risen. I could see Oia, our final destination, and I could almost taste the celebratory sparkling lemonade.

(Seriously, how have I missed out on sparkling lemonade all this time? It’s life-changingly good. On a related note, it is a small miracle I did not have any cavities when I went to the dentist after this trip.)

Overall, the walk was hard. It was sweaty. It took a long time. But the views were insane, and it felt so good to accomplish something that difficult and cool.

If you’re not up for the whole path, you can just do part of it. In that case, I would recommend starting in Oia, walking just past the aforementioned church to the Caldera overlook and then turning back around. Regardless, if you’re planning a trip to Santorini, don’t miss walking at least part of the Caldera. And take a tour with Nikos!