Trail work and wine on Sikinos Island

My parents are still not over it. It’s not the fact that I chose not to visit them over the Easter break—skipping the traditional lamb and family gatherings. It’s that I traded all that for a week of weeding, branch-chopping, and stone-clearing on a remote Cycladic island. The irony isn’t lost on them: these are precisely the kinds of chores I habitually avoid on our ancestral farm. My only excuse? Now that I’ve had some training already, I’ll approach the olive grove with new vigor. Alas, they remain unconvinced.

View of Kastro and Chorio villages from Virgin Mary Chrysopigi Holy Convent

But let’s move on to our main topic. Have you ever wondered who maintains the trails you hike? In countries with robust public services, it’s often state forestry departments or municipal bodies. In Greece, with our charmingly limited resources, that responsibility frequently falls to volunteers and local hiking associations. That’s how I found myself spending Easter on Sikinos, alongside EPOS Filis—a hiking club from Athens—restoring the island’s ancient paths.

Giving instructions

Sikinos is a modest island in the Cyclades, sandwiched between Ios and Folegandros, north of Santorini and south of Milos. It’s small and discreet, with just two villages and a single road linking them. With only about 180 permanent residents, it’s easy to overlook—by travellers, by the state, by almost everyone. Its cliffs and craggy hills leave it with few easy-access beaches, unlike its popular neighbors. But what it lacks in seaside lounging, it makes up for in hiking potential. That’s the local pitch anyway, and that’s why Sikinos needed our help.

The beach at Alopronia
The houses at the Castle
Santorini in the mist, as seen from Troulos peak on Sikinos

Now, when I say hiking, you should recalibrate your expectations. This is the Cyclades: the tallest vegetation here is likely oregano. There are no forests, no pine-covered ridges. Just low, aromatic shrubs and a maze of dry-stone terraces—the leftovers of centuries of patient land-shaping. To farm on these steep hills, locals since antiquity built retaining walls to carve steps into the terrain. A network of footpaths emerged to link fields, chapels, and shelters. These trails, with cultivation long abandoned for the sake of modern living, now attract the boots of hikers—if they can be kept open.

The hills of Agia Marina
Terraced fields and Folegandros island in the background

Indeed, we have to keep in mind that in the old days, people on the islands did not stay close to the sea, to protect themselves from pirates. They hid away and built their villages and castles on hills, so that their settlements would not be visible from the sea and that the island would appear desolate.  That’s the case with Sikinos as well. The ancient settlement was built on the steep cliff of Agia Marina, and at the stepped plains surrounding it the locals were able to grow wheat and wine. The wheat is long gone, but the vineyards endure, yielding a wine that once competed with—and even supplied—Santorini’s own. That’s how good their wine is.

The church of Agioi Anargiroi
Hard at work
A view towards misty Ios and Naxos islands

We arrived on the island and were welcomed warmly by the island’s mayor and the local archaeological supervisor, while our accommodation and meals were generously provided by the Association of Sikinos Migrants in Piraeus. Such is the reality for many small islands—depopulation and economic stagnation, countered only by the stubborn love of those who left and still care. Our mission was to restore and mark a loop trail that climbs to Troulos, the island’s highest point, offering a 360° view over the surrounding Aegean. The trail begins near Agioi Anargyroi, ascends to Troulos—a summit marked by a humble cement cylinder—and then splits. One branch heads toward Agios Mamas and the ancient well of Posta, the other descends past Stamatini to the church of Pantokratoras.

The highest point of the island, Troulos
Abandoned terraced fields

The work was demanding. The schinus shrubs, although low to the ground, have trunks thick and stubborn enough to challenge any handsaw. Thorny bushes added to the battle. Still, there’s a unique satisfaction in wiping sweat from your eyes and gazing out at the sea from a newly cleared trail. Even more rewarding: slipping into the cold, clear sea after a long day’s work, when the salt starts stinging fresh scratches you hadn’t even noticed. Our days followed the same routine. Mornings were for trail work, afternoons for scouting or swimming, evenings for food and wine at the only two open tavernas in Kastro, the largest village. In our free hours, we hiked to Dialiskari and Agios Georgios, the two more remote beaches. We drank wine and ate oven-baked chickpeas while watching the sunset from Malalis Winery—which boasts a sunset comparable to that of Oia in Santorini. On Easter Sunday we rested, joining the local festivities: (underwhelming) roasted lamb, music, dancing, and strong wine. On our last morning before departing, we aimed for a short hike to Agia Marina peak.  Predictably, we didn’t make it, since we poured ourselves a bit too much work hard-party hard during our last night on the island.

The local priest is an excellent violin player
Agios Georgios beach
Dialiskari beach
Vineyards at Manalis winery
Wine from Sikinos with a view to the entire Cyclades Archipelago

Though the island lacks major tourist infrastructure, it offers a few gems. The most striking is the Mausoleum of Neiko at Episkopi—a rare Hellenistic monument unusually well-preserved, not through neglect but through transformation. Neiko, likely a wealthy woman exiled here during the Roman era, became a figure of local legend, her tomb eventually repurposed into a church. The structure, patched and rebuilt multiple times and used as a Christian monastery, has a slightly Frankenstein quality—but it endures. Its survival is a testament to the habit of Sikinos’ people of making do, of adding rather than erasing.

The mausoleum of Neiko at Episkopi

But that’s the beauty of a place like Sikinos. You don’t have to do much. Just being there, contributing in some small way, is enough. The trails will still be there next time, Mr Costas assured us that they will maintain them. And maybe, just maybe, my parents will finally believe I’ve learned to love manual labor. Here you’ll find the relevant trail recordings from Pantokratoras church, from Agioi Anargiroi church and from Alopronia to Dialiskari and Agios Georgios beaches. The path we cleared up is not visible on the map of alltrails yet, so I am looking forward to seeing it up there. You can read more hiking posts under the tag hiking. If you liked this article, share it with your friends. You can also follow this blog, and follow me on Instagram or Facebook, to never miss a post. Until next time!

From Pantokratoras church to Agioi Anargiroi, below troulos

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