There’s something almost poetic about hiking in Santorini in autumn – when the island exhales after the summer crowds have gone, and the caldera glows in softer, golden light. Explore our top favourite Santorini hiking trails below!

1. Oia to Fira: The Legendary Caldera Trail

No experience of hiking in Santorini is complete without the island’s crown jewel – the Oia to Fira trail. Starting right outside Charisma Suites, this 10.5 km (6.52 miles) path traces the spine of the caldera, offering uninterrupted views of the Aegean and the volcanic islets of Nea Kameni and Palea Kameni. 

The trail weaves through the whitewashed villages of Imerovigli and Firostefani, where blue-domed churches and cascading bougainvillea make for postcard-perfect stops. Difficulty level: moderate, with a few rocky sections. Allow three to four hours for a leisurely pace – and plan to begin early to catch the honeyed light as it illuminates Oia’s domes. Autumn’s crisp air makes hiking in Santorini here an utterly magical experience.

After your hike, reward yourself with a sunset sail with Santorini Yachting Club, departing from nearby Ammoudi Bay. Glide past the same cliffs you’ve just conquered on foot — champagne in hand — and watch the caldera transform under the fading light. It’s the perfect complement to a day spent hiking in Santorini.

2. Pyrgos to Prophet Elias Monastery: A Walk Above the Clouds

For those who prefer solitude and sweeping island panoramas, the trail from Pyrgos village to the Prophet Elias Monastery is a must. This 3 km (1.86 miles) uphill hike climbs to Santorini’s highest point, 567 meters above sea level. Difficulty: moderate to challenging, but the views reward every step. Along the way, hikers pass old stone walls, wild herbs perfuming the air, and remnants of ancient terraces. 

At the summit, the monastery stands as a timeless sentinel, offering 360-degree views that stretch from Akrotiri to Oia. In autumn, the light is crystal clear – a photographer’s dream for hiking in Santorini.

3. Emporio to Vlychada Beach: Through Santorini’s “Badlands”

This lesser-known trail showcases a different face of the island. Beginning in Emporio, a charming medieval village of labyrinthine alleys and Venetian towers, the 7 km (4.34 miles) path winds through a surreal landscape of ochre cliffs and sculpted canyons. Known as the “Badlands of Santorini,” this route feels almost lunar. 

The final descent to Vlychada Beach, with its moon-white volcanic formations, is spectacular. Difficulty: easy to moderate. Autumn’s softer light casts long shadows across the canyons, making this one of the most atmospheric routes for hiking in Santorini.

4. Akrotiri to the Red Beach and Ancient Akrotiri

History lovers will adore this short but fascinating 4 km (2.48 miles) loop trail. Starting at the village of Akrotiri, it passes by traditional windmills before reaching the prehistoric settlement of Ancient Akrotiri, Santorini’s own “Pompeii.” Continue on toward the Red Beach, whose rust-colored cliffs and cobalt waters are unforgettable. Difficulty: easy, though the descent to the beach can be steep. 

In autumn, the crowds are gone, and you can enjoy this iconic stretch of hiking in Santorini in near solitude, with the scent of sea salt and thyme in the air.

Before returning to Oia, stop for a leisurely dinner at Sunset Tavern or Basalt Restaurant, right on Ammoudi Bay. The day’s fresh catch, paired with chilled Assyrtiko and the glow of lanterns on the water, creates an experience as memorable as the trails themselves. It’s the quintessential Santorini evening after a day of hiking in Santorini.

5. Megalochori Caldera Path: A Secluded Vineyard Walk

For a gentler experience, the Megalochori trail offers the perfect blend of nature, tradition, and romance. This 5 km (3.1 miles) circular route starts from Megalochori Square and winds through vineyards, old chapels, and hidden caldera viewpoints. Difficulty: easy. Pause at the Heart of Santorini, a natural rock formation framing the sea – a beloved spot for proposals and sunsets. 

Autumn brings the grape harvest, and the scent of fermenting wine fills the air, reminding you that hiking in Santorini can be as sensual as it is scenic.

Back at Charisma Suites, reward your day’s adventure with a sunset cocktail on your private terrace. Watching the horizon blush pink over Oia’s cliffs, you’ll understand why autumn hiking in Santorini isn’t just about exploring trails – it’s about rediscovering the rhythm of the island itself.

Explore more Santorini autumn tips: Autumn in Santorini: The Secret Season for Serenity and Sunsets