I had always fancied myself as the sort of person who could navigate a Greek ferry timetable with the same casual confidence I bring to reading a pub menu back home. Turns out I was wildly mistaken, and my first introduction to Ambela Syros Cyclades involved me sprinting down a harbour in Piraeus with a rucksack bouncing against my spine like an enthusiastic toddler, shouting apologies in broken English to anyone who would listen. I had misread the departure time by a full hour, which in ferry terms is the difference between a gentle holiday and a cardiac event.

When I finally collapsed onto the deck, sweating through my linen shirt in a way that suggested I had just completed a marathon rather than a mildly brisk jog, I had plenty of time to contemplate my life choices. The Aegean stretched out before me, impossibly blue and entirely indifferent to my suffering. Four hours later, Syros emerged from the haze like a promise, all terracotta rooftops and hills that looked distinctly walkable from a distance.

The approach to Ambela itself nearly made me forget the morning's indignity. The property sits in a spot that feels properly secluded without being inconvenient, surrounded by the sort of dry stone walls and scrubby vegetation that makes you want to immediately adopt a Mediterranean lifestyle and never look at a British winter again. I dumped my bags with the enthusiasm of a man who had not properly understood what Greek sun could do to a pasty complexion, and set out for what I had planned as a gentle afternoon stroll to Ermoupoli.

Here is where I must confess my fundamental misunderstanding of Cycladic weather. I had packed with the British assumption that "warm" means "perhaps remove your jumper." Greek warm, I discovered, is an entirely different category of experience. Within twenty minutes of walking, I had progressed from pleasantly warm to wondering if my eyebrows were melting. The path wound through olive groves and past the occasional stone cottage, each turn offering views that would have been breathtaking had I any breath left to give.

I had intended to walk the coastal path proper, a route I had researched with the obsessive detail of a man planning a military campaign. The reality involved me finding a patch of shade beneath a particularly generous carob tree and reconsidering my entire relationship with physical exertion. A local cat joined me, looking at me with the undisguised contempt that only cats can manage, as if to say that even the animals had more sense than to march about in the midday heat.

The following morning, wiser and significantly more sunscreened, I attempted the walk to Galissas. The weather had shifted to something more accommodating, with a breeze that felt almost British in its thoughtfulness. This time I set off at dawn, when the light turns everything golden and the temperature still remembers what comfort feels like. The trail proper begins near the property, winding through terrain that demands proper attention, loose scree underfoot and the occasional thorny shrub determined to reclaim your walking trousers.

I found myself alone for stretches that felt properly wild, the sort of solitude that makes you talk to yourself just to confirm you still exist. The path climbs gently, offering glimpses of the sea that expand with each metre gained, until suddenly you are looking down on bays that appear on no postcard, too small and perfect for mass tourism.

By my fourth day, I had developed something approaching a routine. Early walks before the sun asserts dominance, then retreat to the terrace with coffee and the sort of breakfast that makes you wonder why you ever bothered with cereal. The property's position means you can step straight out into landscape that demands exploration, though I learned to carry more water than I thought necessary and to respect the fact that Greek hills have been defeating overconfident walkers since before the Olympics were invented.

One evening, attempting what I had assured myself was a gentle sunset walk, I found myself caught in a wind that appeared from nowhere, the sort that whips up dust and sends you scurrying for shelter with your dignity in tatters. I took refuge in a tiny chapel, its door unlocked in that trusting way that still surprises a Londoner, and sat listening to the wind batter the shutters while the sky turned colours no camera could capture.

Sitting there, slightly ridiculous in my walking gear and my carefully planned itinerary in complete disarray, I felt something shift. The mishaps, the heat, the unexpected wind, they had become the point rather than the obstacle. I had arrived planning to conquer walks and tick viewpoints from a list. Instead I found myself adapting, surrendering to rhythms older than my need for achievement.

My final morning, I walked only as far as the headland above the property, nowhere ambitious, nowhere I had not been before. The weather had turned soft, grey almost, reminding me uncomfortably of home. I stood there watching the ferry approach that would carry me back to reality, and realised that the best walks had been the ones that did not go to plan, the mornings when I turned back early, the afternoons when I found somewhere unexpected and simply stopped.

I left Syros with legs still aching slightly, a tan that would fade within a fortnight, and the certain knowledge that my next holiday would involve equally poor planning and equally wonderful mistakes. Some places teach you that the walk matters more than the destination, and occasionally the best thing you can do is find a shady tree and admit defeat with whatever dignity remains.