Greece 2026 - Day 5, Santorini
1 May 2026
Santorini, Greece
Weather: Strong winds, partially cloudy and gloomy skies. Sunny at times. Passing shower in the evening.
The day started the way most good days do, with coffee and pies at our favourite Picolo before setting off on what was supposedly a three hour hike from Fira to Oia. Like many things in life, the estimate proved wildly optimistic.
Our first major stop was Skaros Rock. What looked like a quick detour turned into a two hour adventure. The dramatic cliffs, endless caldera views and a hidden church tucked into the rock face kept drawing us deeper in. Every corner seemed to demand another photograph. By the time we finally left, we realised we had only made it as far as Imerovigli.
A collective search for toilets led us to Dear Elie Café, a decision that turned out to be one of the smartest of the day. Coffee became brunch, water bottles were refilled, and morale was restored. Beyond that point there would be no facilities for another six kilometres, making the stop feel less like indulgence and more like survival planning.
The hike from Imerovigli to Oia was easily one of the highlights of our Santorini trip. Strong winds kept us cool while the clouds shielded us from the sun. Along the way, the views became increasingly spectacular. The cliffs stretched endlessly beside us while Firostefani and Imerovigli slowly receded into the distance.
Six hours and more than ten kilometres later, we finally arrived in Oia. Our reward was lunch at Thalami, recommended by our Spiridakos driver. The recommendation was spot on. Good food, good wine and sensible prices. Exactly what weary hikers needed.
Dessert at Melenio came with free entertainment. Tourists lined up beside our table to capture one of Oia's famous Instagram spots while an assortment of colourful characters provided people watching opportunities.
Back at Agali, there was just enough time to freshen up before heading to Fira for dinner at Aris and it proved a wonderful place to end the day. Perched above the old port with sweeping views of the caldera, it combined warm hospitality with excellent food.
As dinner ended, the rain finally arrived. We lingered indoors listening to stories from the restaurant captain, who shared old photographs and snippets of local history while teaching us a supposedly easier "chook chook chook" route back to town.
In the end, we took the shortcut and walked through the rain along the main road back to our hotel at Firostefani.
A long day. A windy day. A wet day.
