Hiking the Hidden Trails of Skiathos: From Coastal Paths to Mountain Peaks

Let me be straight with you: Skiathos isn't the Alps, but don't underestimate these trails either. The island packs surprising elevation into its compact 44 square miles, with paths that range from gentle coastal strolls to quad-burning climbs.

Before hitting any trail, invest in proper footwear. My hiking sandals have been perfect for the coastal routes where you might want to dip your toes in the water, while I switch to my trail runners for the more rugged inland paths.

Most importantly, don't skimp on water. The Mediterranean sun is no joke, especially when you're climbing those exposed hillsides. I've learned the hard way that a standard bottle isn't enough—now I never hike without my hydration pack, which holds enough water for a full day of exploring and distributes the weight comfortably.

Cell service can be spotty in the mountains, so download offline maps before heading out. I've found that the AllTrails app has most Skiathos routes well-documented, though sometimes the locals know paths that aren't on any digital map.

My absolute favorite trail in Skiathos begins near Troulos Beach and winds through pine forests to the island's most important religious site, the Monastery of Panagia Kounistra. This 4-mile route (round trip) offers that perfect balance of accessibility and reward that makes for an ideal couples hike.

The path starts gently enough, following ancient stone walls past olive groves where you'll likely spot local farmers tending their trees. About a mile in, you'll climb through fragrant pine forest where the only soundtrack is birdsong and the distant whisper of waves. I've spotted red squirrels darting between trees here—keep your eyes peeled!

When you emerge from the forest, you're treated to sweeping views across to neighboring Skopelos (yes, where they filmed Mamma Mia!). The monastery itself is small but charming, with whitewashed walls and a bell tower that stands out against the impossibly blue sky. The nuns sometimes offer visitors homemade honey and liqueurs.

For this trail, I recommend packing a small picnic blanket for a romantic lunch stop with a view. There's a perfect spot just before reaching the monastery where you can see half the island spread out before you.

For couples who love a good challenge, the hike to Skiathos' highest point—Mount Karafiltzanaka at 1,420 feet—delivers both physical exertion and jaw-dropping panoramas. This isn't a casual stroll, but the effort-to-reward ratio makes it worth every drop of sweat.

The trail begins near Agia Eleni Beach on the northwest coast. I recommend starting no later than 8 AM to beat the heat. The first section climbs steadily through pine and oak woodland, where dappled sunlight creates a magical atmosphere. My daughter once described it as "walking through a fairy tale," and I couldn't agree more.

The middle section gets serious with some steep switchbacks. This is where I'm always grateful for my trekking poles, which save my knees on both the ascent and descent. Don't rush this part—take breaks to catch your breath and admire the increasingly spectacular views.

The final approach to the summit opens up to reveal a 360-degree panorama that literally stopped me in my tracks the first time I saw it. On clear days, you can see not just all of Skiathos but neighboring islands like Skopelos, Alonissos, and even mainland Greece in the distance. There's something incredibly romantic about standing on top of an island together, with nothing but sky and sea stretching to the horizon.

The summit has a small chapel and a perfect picnic spot. We once shared a bottle of local wine here (pack it in, pack it out!), watching the sunset paint the Aegean in shades of gold and pink. Pure magic.

One of the most magical aspects of hiking in Skiathos is discovering beaches accessible only by foot or boat. The Mandraki Bay Trail delivers exactly this kind of exclusive experience—perfect for couples seeking privacy away from the crowded shores.

This moderate 3-mile trail begins near Koukounaries Beach (already stunning in its own right) and follows the coastline through fragrant pine forest. What makes this route special is how it hugs the dramatic coastline, offering constant peekaboo views of turquoise waters below.

About halfway through, you'll reach a fork—take the path leading downhill to discover Mandraki Bay, a perfect crescent of golden sand embraced by rocky headlands. The first time I rounded that final bend and saw the empty beach below, I literally gasped out loud. Even in high season, you might have this slice of paradise entirely to yourselves.

This is where my packable beach towel and waterproof phone case earn their keep in my pack. The swimming here is divine—crystal clear water with excellent snorkeling along the rocky edges of the bay.

For the ultimate romantic experience, pack a light lunch and a chilled bottle of local white wine (Assyrtiko is my go-to Greek variety). There's no better feeling than having earned your beach day with a beautiful hike, then cooling off in pristine waters that most tourists never see.

For a perfect blend of nature and culture, the network of old donkey paths connecting Skiathos Town to inland villages offers a glimpse into the island's authentic heart. My favorite route is the 6-mile loop from Skiathos Town to the abandoned settlement of Old Skiathos and back.

Starting from the new port area, follow signs for 'Kastro' (the old fortress). The path quickly leaves the tourist zone behind, climbing through olive groves and small family farms where you might be offered fresh figs or cherries in season. I've found that carrying a small travel phrase book helps with these delightful encounters—the older locals especially appreciate visitors who make an effort with a few Greek phrases.

After about an hour of gentle climbing, you'll reach a ridge with spectacular views back toward town and the harbor. This is where I like to break out my compact binoculars to spot returning fishing boats or distant islands on clear days.

The highlight comes when you reach the ruins of Old Skiathos, the original settlement founded in the 14th century. The stone buildings are slowly being reclaimed by nature, creating a hauntingly beautiful landscape. The ancient fortress walls still stand in places, and the small Byzantine church has been partially restored.

Take time to explore the narrow pathways between ruins—this is where the island's history feels most tangible. On my last visit, an elderly local shepherd was playing traditional music on a handmade flute near the old church. These unexpected cultural encounters are what make hiking in Skiathos so much more than just exercise.