Santorini Island – in search of joyful wandering

Santorini Island – in search of joyful wandering

How to spend a few days on the island

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Leading up to May, I felt weathered, worn down from the consistent and unending demands of work. I could sense my limits tested, as my indomitable cheerful disposition had begun to erode each day, just a stream carves out a canyon from granite. However, happenstance led me to Santorini for a wedding, the perfect destination to coincide with the need to rejuvenate

Rejuvenate I did by practicing the art of flâner – the art of observing and strolling through a city, as coined by the French – along Santorini’s mountain-top towns. Taking advantage of jet lag, I found serenity in the panoramic mountain views, navigating off-hours in solitude the cliff-hugging trails.  

Flâner implies a quiet and confident freedom. Santorini’s cliff walks between Oia and Fira are a safe space to practice this art. While the narrow pathways and steep stairs will challenge you, the village limits are restrained by cliff edge, acting as guard rails against getting lost.

Santorini island, known as Thera to the ancient Phoenicians, is crescent-shaped, famous for its panoramic views of the sunken volcano caldera at the center of the crescent, densely packed white-washed stone homes and churches built into steep cliff walls, and stunningly red sunsets. The densely packed cave dwellings crest the ridge; the alabaster-white domed roofs, sapphire pools and church domes fill the upper parts of the cliff which lead another 500-1000 feet below. The scene inspires visions of mythical places. For me, Lord of the Rings comes to mind, as the towns conjure an image crossed between Gondor and Hobbiton. Easy to see why Santorini has been profiled as Greece’s most Instagrammable island. It is also an economic bright spot for the country, with international flights to the island doubling the past 10 years.  

Visiting from Boston required three flights. While staying 3 full days between midday Friday to midday Monday in May seemed short, the density of sensations from navigating the maze-like towns along the slope of a cliff seemed to stretch the days longer and the relaxation deeper. Every intersection presents a decision to go up, down, or forward as if you’re navigating in 3-D. At times, it was hard to move on, as each corner offered a new view of countless unique villas, bungalows, dwellings, cave homes, and cliff-side apartments. I’ve never seen such a high density of infinity pools, ranging from olympic size swimming pools to kitchen islands. Getting lost in the beauty and awe-inspiring architecture was never easier thanks to the labyrinth of paths to navigate

Flying from the US does present challenges with the time-zone change; however, it’s to your advantage if you aim to wander. I found that during the day, around 10AM the crowds become thick, especially in the tourist hotspot of Oia. This is the hottest time of day, and often too bright for photography, overexposing photos.

If you’re feeling worn down and looking for an escape to Santorini, I recommend the following program:

  • 6-8AM, I found a moment of serenity during a morning walk between Imerovigli to Fira and back again. That Sunday morning felt like peace on earth, as the sun was shining and rising in the east, leaving Imerovigli and Fira draped in the blue shadow of the early morning. Not a single motorcycle or car was to be heard. The army of cleaners that are normally seen wiping down the white plaster and sweeping the walkways were absent too. Few people were in the streets or alleys. Just singing sparrows, the occasional runner or walking couple, and committed photographers. 
  • 7-9PM, Set-up to view the sunset over the sea and long-exposures of the cliffside homes. Oia offers an uninterrupted view of the sunset, while Imerovigli shows greater depth, with Oia in the foreground. The hue in the sky as the sun sets seems redder here than in the US, maybe because of the extra distance to the horizon that comes from standing on the cliffs. On the horizon, you can see Avoladonisi island, part of the Cyclades chain, and as the sun sets, the island grows darker in contrast. Imagining myths and tales about gods and monsters would be a fun pastime for any shepherd or mariner back in the day. As the sky grows darker, the light from the horizon contrasts with the islands to form dark shapes. 
  • Whenever you’re not taking a nap during the day – walk the trails. There is a 1.5 – 2 hour hike from Imerovigli down to Skaros, remnants of an old Venetian fortress. On the backside is a practicing monastery today. A longer hike is the trail from Oia to Imerovigli, 8 kilometers, winding through the towns and then along the ridgelines between the towns. Bring water, as there are no vendors between the two towns and the hot sun and sea breeze are a recipe for dehydration. Wear sturdy shoes to avoid blisters the next day. Small pumice rocks make the trail bumpy and at times slippery, as you step off with your foot.

Spending more time in Santorini would be easy; as I did not even explore its wine and food scene, historical sites and museums, or visit any beaches on the gentler east side of the island. However, a 3-day immersion, navigating gorgeous cliff-side towns was exactly what I needed, a deep relaxation. I feel there is an untapped genius in all of us to navigate landscapes, and Santorini brings this out intuitively. Maybe it’s the clear view of the water, sun, and the slope of the mountain all at once, this view acts an invisible hand, instinctively guiding us gently as we roam the cliff-side towns.