The Challenge

The southwest part of the island, characterised by the Lefka Ori mountains, dramatic gorges, secluded beaches, and clear blue waters, is more rugged and less visited. As we trek, we learn that this region was the focal point of the Battle of Crete from World War II, where fierce fighting occurred between Allied forces and German paratroopers.

The final day is spent finding out more about the Battle, with a military expert, visiting the important sites where we can pay our respects.

The Details

Where is it?

Crete, Greece.

When is it?

6-12th September 2027

How much is it?

Registration fee: £425 (£375 early bird discount ends 30 November 2026). 

Fundraising target: £3,400pp (£2,000 due by 14th June 2027)

What's included?

All accommodation, activities, food, transportation during the challenge, local guide and insightful historian, celebration meal at the end. The Frontline Walk training plan, T-shirt and FLW goody bag will be part of the package too!

What's excluded?

International flights, transportation before and after the challenge, personal expenses.

Your itinerary

Day 1: Arrival and Historical Exploration

We arrive in Chania, a picturesque town on Crete's northwest coast. Chania's port was a key Allied supply point during WWII, especially in the Battle of Crete. On May 20, 1941, German paratroopers landed here as part of Operation Mercury, their last major airborne assault of the war. After meeting our local team, we head to Hora Sfakion, stopping at the privately-owned Historical War Museum in Askifou, filled with WWII memorabilia. After checking into our hotel, we’ll have time for a quick swim before dinner.

Day 2: Coastal Trek to Anopoli

Our trek begins in Hora Sfakion, a village between the sea and the White Mountains. We hike along the coast following a narrow cliffside path, with the option to clip onto an embedded wire for a short distance, mini ferrata style. Mid point we reach Loutro, a remote village once a pirate lair and later a hideout for Cretan resistance and British intelligence during WWII. We continue to Anopoli, passing ancient ruins, Venetian fortresses, and Byzantine churches. Approximate distance: 11 km; ascent: 900 m; descent: 350 m.

Day 3: Coastal Walk to Agia Roumeli

After leaving Anopoli, we take a short transfer to Agios Ioannis and follow a coastal track with stunning sea views. We rest at the ancient chapel of St. Paul, enjoying a cold drink and a swim. The trek ends in Agia Roumeli, one of Crete's wildest regions, where we can relax on the pebble beach. Approximate distance: 10 km; ascent: 14 m; descent: 779 m.

Day 4: Samaria Gorge Adventure

Starting in Agia Roumeli, we trek through the 16 km-long Samaria Gorge, famous for its breathtaking scenery and towering limestone cliffs. The gorge was a critical escape route during WWII. We’ll pass the "Iron Gates" and the Samaria Village, where the King of Greece hid in 1941. We finish at Xiloskalo and transfer to our guesthouse. Approximate distance: 16 km; ascent: 2222 m; descent: 987 m.

Day 5: Summit of Kouloule

Our challenge peaks as we ascend to Kouloule, 1631 m above sea level. The rocky path requires careful footing, but the panoramic views are worth the effort. After reaching the summit, we continue along the ridgeline to Kalergi Refuge for lunch, then descend to Samaria for our transfer back to the guesthouse. Approximate distance: 9 km; ascent: 1009 m; descent: 1009 m.

Day 6: Battle of Crete Sites

We visit key WWII sites, including Maleme and the Allied War Cemetery at Souda Bay, gaining a deeper understanding of the Battle of Crete and its lasting impact. The afternoon is free to explore Chania.

Day 7: Final Day in Chania

After breakfast, enjoy some last-minute exploring and shopping in Chania’s picturesque Venetian harbour before our final lunch together.