The Battle of Crete: An In-Depth Traveler’s Guide

On the morning of May 20, 1941, 22,000 German parachutists skydived on Crete, launching one of the most significant airborne invasions in history.  The targets were vital airfields and strategic positions, and the aim was to secure the island and quickly control the Mediterranean Sea routes. What the invaders didn’t expect was the fierce resistance from the Cretan civilians. The Battle of Crete had just begun.

Men, women, children, and elders, armed with improvised weapons like their agricultural tools (scythes, spades, and pitchforks), clubs, kitchen knives, old Balkan War-era rifles stored in homes and museums, or even with bare hands, took part in ambushes, sabotage, and frontline fighting, showing fierce loyalty to their island and allies from Britain, New Zealand, and Australia.

Xan (Alexander) Fielding was a British author, translator, and journalist who served as a Special Operations Executive (SOE) agent in Crete, undertaking espionage, sabotage, and resistance activities against Axis forces. He writes:

“As dawn broke over the rugged peaks of Crete in 1941, the skies churned with German gliders pouring troops into Heraklion and Maleme. The fierce resistance mounted by the Cretans, alongside the Allied troops, was remarkable. I found myself drawn deeper into the island’s defiant spirit—living among shepherds, learning their ways, and joining in small-scale sabotage and intelligence missions. The mountains became more than just a refuge—they were our fortress, the stronghold where courage blossomed amidst hardship. Despite the danger from relentless German patrols and air attacks, the determination of the local people and their unyielding hospitality gave hope amid the chaos.”

Fielding, Xan. The Stronghold: Four Seasons in the White Mountains of Crete. London, 1955

The Germans planned a series of parachute assaults targeting Allied airfields on the island’s north coast, particularly to seize Maleme Airport, which was key to bringing in reinforcements. Approximately 22,000 German troops participated in the airborne offence, transported by over 500 Junkers Ju 52 aircraft.

Meanwhile, the allies were preparing their defence. They knew about the impending German attack on Crete primarily through intelligence gained from Ultra, the British decryption of German communications using the Enigma machine. 

By 17 May 1941, the garrison on Crete included about 15,000 British troops, 7,750 New Zealanders, 6,500 Australians, and approximately 10,200 soldiers from mainland Greece. On 19 May, an additional 700 men from the Argyll and Sutherland Highlanders were transported from Alexandria to Tymbaki overnight. 

Under the command of New Zealand General Bernard Freyberg, the Allies initially had the advantage as the German paratroopers were vulnerable targets during their descents. Using their scythes and pitchforks, the Cretans killed German soldiers immediately upon landing from their parachutes. This resulted in heavy casualties among the German troops and armed the Cretans with much-needed modern guns. 

George Psychoundakis was a Cretan shepherd who served as a dispatch runner for the Special Operations Executive (SOE) on Crete, carrying messages across rugged terrain. In his memoir, The Cretan Runner, he writes:

“Out of the sky, the winged devils of Hitler were falling everywhere: German parachutists rained down upon us, darkening the heavens like a swarm of angry bees in a bee-garden. Furious villagers set upon one grounded plane until it was little more than a broken heap, a bit of bread thrown onto an ant-hill. The enemy reached into the very bowels of our land and provoked a storm in the soul of the race like the hiss of a poisonous snake about to strike. The Cretan people’s rage was volcanic, born of centuries of fighting invaders, and it surged with a fierce and unyielding energy that took the Germans by surprise.”

Psychoundakis, George. The Cretan Runner: His Story of the German Occupation translated by Patrick Leigh Fermor, London 1955

In Chania, the night of May 20-21 was critical. The strategically vital Tavronitis Bridge, which connected the provinces of Chania and Kissamos and provided a route to Maleme Airport, was a key objective for the Germans. 

Despite strong resistance, the Germans managed to establish a bridgehead east of the Tavronitis River, opening the way to the crucial Hill 107, overlooking the Maleme airport. The New Zealand 22nd Battalion defended the Hill under the command of Lieutenant Colonel Leslie Andrew. The intense Luftwaffe attacks had severed the lines, which made coordination extremely difficult. Without full knowledge of the situation and under the mistaken belief that his battalion was lost, Andrew urgently asked for reinforcements, which were denied. 

After a failed counterattack, he withdrew to regroup. Meanwhile, parts of the battalion, unaware of the withdrawal, also pulled back. This left strategic Hill 107 and the airport undefended, allowing German paratroopers to move in and take Maleme without resistance. With the airport secured, the Germans were able to land reinforcements and equipment, shifting the balance of the battle in their favour.

The highly acclaimed British military historian, Anthony Beevor, writes:

“At around 8 am on 20 May 1941, German gliders appeared in the sky over Maleme. This was followed by transport planes unloading paratroopers and supplies. The New Zealand battalions defending the airfield opened heavy fire, inflicting severe casualties. Cretan civilians joined the fight with improvised weapons, making the landing fiercely contested. Despite initial German losses, they succeeded in digging in near the airfield. The defending New Zealand troops held the strategic Hill 107, but due to communication failures and mistaken assumptions, their command ordered them to withdraw from this crucial high ground. The loss of Hill 107 enabled German forces to seize Maleme airfield, allowing continuous air reinforcements to reach the front. This shift enabled the Germans to outnumber and outgun the defenders, ultimately deciding the battle for the entire island.”

Beevor, Anthony. Crete: The Battle and the Resistance. Oxfam, 1991

Following the loss of Maleme Airfield, the Allies were pushed back to the west-south coast of Crete, near Sfakia. The Royal Navy planned to evacuate 10,000 allied forces between May 29 and June 1. However, the majority of British, Australian, and New Zealand soldiers remained in Crete. Some of them managed to escape the Germans and continued to help the island against Nazi rule.

An important figure in the Battle of Crete was the British archaeologist John Pendlebury (1904-1941). John had lost one of his eyes during childhood and wore a glass eye for the rest of his life. He studied archaeology at Cambridge University, and in 1930, Sir Arthur Evans, the excavator of Knossos, appointed him curator of the site. His passion for Crete eventually led him to fight along the Cretans, functioning as a Special Operations Executive (SOE) for the British allies. Pendlebury was a close friend of Antonis Grigorakis, also known as Satanas, a key figure in the history of the Cretan Resistance. On May 20, 1941, Pendlebury and Satanas were stationed on the Venetian Walls (near Chanioporta) to defend Heraklion against German troops. The next day, Grigorakis headed to his home village, Krousonas, and Pendlebury followed him through a different route. In the neighbourhood of Kaminia, a small group of German parachutists traced and executed Pendlebury, whose death caused great sadness to the dozens of Cretans who knew him. His corpse was never found. A cenotaph under his name is found today in the Cemetery of Souda, Chania. 

The allies were determined to save as many soldiers as possible. The evacuation began on May 29, with the first ships leaving Sfakia for Egypt as the remnants of the so-called Creforce crossed the Askifou Plain. 

The New Zealand 4th and 5th Brigades set up defensive positions to protect the retreating troops as they moved toward the beaches. The Australians, meanwhile, held out in Rethymno and Heraklion. The bravery of the Allied forces exemplifies courage under fire—facing dangerous airborne assaults, enduring supply shortages, and sustaining heavy losses, yet still fighting with discipline, heart, and hope. However, they suffered heavy losses from air attacks on the ships. 

Ultimately, only about 4,000 troops could be squeezed onto vessels on the last night of evacuation (31 May) while approximately 6,500 were left behind. Some of them were captured by the Germans and held as war hostages. Others managed to hide and join the Cretans in their resistance war against the Germans. 

For the following three years, the Cretan people supported, hid, and fed these people at great personal risk, resulting in a lasting bond between the Allied (ANZAC) soldiers and the Cretans—a friendship grounded in mutual sacrifice for freedom that continues to be remembered and honoured to this day.

George James Doundoulakis (1921–2007) was a Detroit-born Greek-American whose family moved to Crete when he was little. In 1941, George served as a translator for the Greek and British army headquarters in the village of Archanes. After the German invasion and the defeat of Allied forces, many soldiers were left stranded and unable to evacuate. Montague “Monty” Woodhouse, the British SOE (Special Operations Executive) chief on Crete, impressed by George’s skills and knowledge, recruited him to support the SOE. George formed an underground resistance organisation along with his brother Ilias and friends, recruiting ex-military personnel and civilians.

This group became one of the first Cretan resistance cells. Among their actions was the sabotage of Kastelli Airport, where George, Kimon Zografakis, and British commandos planted explosives that destroyed German planes and fuel supplies. Intelligence from George’s network also contributed to the Royal Air Force bombing of a German convoy meant to supply Rommel’s Afrika Korps.

Eventually, George fled with others through the mountains and was evacuated by British forces to Egypt in 1943. For his courage and critical contributions to the resistance and to helping Allied soldiers, he was later awarded the King’s Medal for Courage in the Cause of Freedom by the British government.

The Battle of Crete was a key moment in military history. The German forces’ brutal paratrooper assault to capture the island and secure a strategic foothold in the Mediterranean was met with unexpected fierce resistance from locals and their allies. This experience led Hitler to reconsider airborne tactics, effectively ending large-scale German airborne operations for the rest of the war. Essentially, the Battle of Crete showed the world how civilian involvement can turn the tide against a technologically superior force.

Culturally, the Battle of Crete remains a cornerstone of Cretan identity and pride. The island’s people, untrained but determined, took up arms—ranging from old rifles to farming pitchforks—to resist the invaders. Their bravery and sacrifice marked forever the Cretan people’s spirit of resistance against occupation. The battle’s story, passed down through generations, continues to inspire both the islanders and Greece as a whole. As in all wars, what was left behind were the personal stories of simple people who did their best to defend their lands and families without thinking of their personal cost. 

In True Cretan, we are proud to collaborate with one of the world’s leading experts on the Battle of Crete. Together, you can visit all the significant battlefields, war museums, and walk the same grounds as soldiers and civilians who lived through the war. You will gain in-depth historical insights through rare archives, personal stories, and photographs. 

For a comfortable experience, we can also book your private transportation, while our booking options are always flexible to suit your needs and requirements. Contact us today to reserve your spot and experience this key chapter of history firsthand!