Kayaking in the Aegean

Following in the paddle strokes of second world war canoe heroes, James Henderson aims for Leros island – albeit with rather less stealth.

Guide Stefanos manoeuvres into shore off Kalymnos
Guide Stefanos manoeuvres into shore off Kalymnos | Image: James Henderson

At the start of the second world war, it would have been hard to imagine the canoe as a vital tool of naval warfare, but in a time of crisis British admirals, and generals were prepared to entertain almost anything. The craft proved surprisingly versatile, and many small canoe-borne units were developed, with an efficacy well out of proportion to their numbers.

These units, forerunners of today’s Special Boat Service, experimented with extraordinary equipment: collapsible boats, semi-submersible submarines, even hand-released torpedoes. They ranged over every theatre of the war, and the Mediterranean in particular.

So I pore over maps, tracing actions around the battle lines of the war, through the Ionian Islands, the Cyclades and the Dodecanese. Yes – there was a spectacular raid on the island of Leros, in 1944. I can track up from Kos, via Kalymnos to Leros. At 50km or 60km of straight paddling, perhaps against wind and current, it will make a seriously stiff challenge in itself – and if the weather kicks up it will be a bona fide extreme adventure. The Aegean is, after all, known to be flukey…

Thursday 1200

Sure enough, messages ping across the ether: “A storm rolling down from the Black Sea, ferries cancelled, trip possibly delayed.” But I have just the one chance. Go, or not go? Eventually, on Friday afternoon, a text: “Ferries back on, kayaks en route to Kos.” They will arrive just before me, at dawn on Saturday.

James Henderson on a lunch stop on southern Kalymnos
James Henderson on a lunch stop on southern Kalymnos | Image: James Henderson

Friday 1800

We take off for Athens, where a few hours’ layover enables me to read up on the history. A bewildering array of units used canoes: Combined Operations Pilotage Parties, Detachment 385, Z Group, SSRU, SRF and Scobbs. Training was incredibly rigorous – and, of course, it was all obsessively secret.

Their most vital role was in reconnaissance. Floated off submarines, teams of canoe-borne men would paddle into the approaches to test for depth and obstructions, probe the firmness of the sand and then crawl up the beach, looking for defences and routes inland. At other times, canoes were used to insert and extract SOE agents and supplies.

And then there were covert raids. Operation Frankton, whose participants were later made famous as The Cockleshell Heroes, took place 70 years ago; but these units moved around the ebb and flow of the war, despatched to go ashore behind the lines and strike targets or attach mines to ships in harbour.

Saturday 0620


On touchdown in Kos, I am taken by Stefanos, my kayaking guide, to the glassy Kos Aktis hotel in town for breakfast on the balcony. Turkey is just a few miles across the sea. Even in the protected bay, the water is jumping in angry bottle-green diamonds. The sun’s rays glint and glance in all directions.

On the map, we trace our route across to Pserimos, around Kalymnos, north to Leros, whose exceptional natural harbour, Portolago, was vital to the Axis supply lines to North Africa. Turns out it’s 70km in all; better get a move on. We head to the beach.

There is an explosion of kit: paddles, life jackets, spray skirts, waterproof bags stuffed into the bulkheads, balers and sponges. And that’s without any bombs or bullets. Everything stowed, we cast off.

Saturday 0900

Pserimos, exceptionally barren, stands hulk-like ahead, sheltering us. But as we cut across the channel to Kalymnos the wind howls. The chop is only 50cm high, but the wind-whips spray off into our faces – it’s perhaps a force four. Then I imagine being out here in the middle of the night, with hostile troops around. We inch our way across.

Guide Stefanos in Kalymnos harbour
Guide Stefanos in Kalymnos harbour | Image: James Henderson

Saturday 1200

We eventually reach the cover of Kalymnos. Here, unexpectedly, the sea is glass-flat and spectacularly clear. The shore is as steep below the surface as above, so I can see 10m to 12m down, past boulders and ledges into the luminous blue. There is no stopping, though; we’ve a long way to go. We make good time on the limpid water, where there is barely a ripple besides our arrow-shaped bow waves, passing Kalymnos’s main port, full of ferries and fishing boats, and then remote and tiny inlets, where motor yachts are tied up for picnics.

Out on the exposed western shore, there is strangely little wind, but the sea, dark blue, is terrible. It shifts in angry bulk, 2m high. We plough on. I hardly dare look but somewhere out there in the Aegean, on a moonless night in June 1944, the unlikely named Earthworm Detachment of the Royal Marines Boom Patrol arrived here in a caïque, a local fishing boat, from their hideout off Turkey. Three two-man canoes – Shrimp, Shark and Salmon – were launched and paddled off to their target. Their mission was to destroy shipping spotted in Portolago.

Saturday 1800

Shoulders aching, we pull in at Panormos, a small beach with a few guesthouses. The best restaurants are in town apparently, so we head back to Kalymnos for dinner on the lively harbourfront. It is calm in town and we find a room in the narrow streets.

The northern end of the island, near Emporios
The northern end of the island, near Emporios | Image: www.alamy.com

Sunday 0800

The wind is still up. Even in the bay, protected by the island of Telendos on one side and Kalymnos’s 300m scarps of bare rock the other, the sea is choppy. Then we emerge into open water. The swell is less than a metre, but the wind is howling. Squalls, dark grey and rippled, whip across the water, thumping me in the chest. Water is actually beading on the surface of the sea; later I discover this means force six.

Between squalls I paddle as hard as I can, but it is dismayingly slow going. At the northern point of Kalymnos, I look across at the vertical rock wall. We are moving at less than 1kph.

Sunday 1130

At the corner, we poke the kayak noses into the channel. The wind shears and the swell boils. It is less than a kilometre across (stories tell of troops machine-gunning one another across the gap) but the crossing to Leros is known as a bad one on far milder days than today.

A cove on Kalymnos
A cove on Kalymnos | Image: James Henderson

This is insane, I decide. It’s time to put sense above valour and turn back. I’m not sure if the Greeks are known for ironic understatement, but Stefanos says, “That, I think, is a good decision.”

The Portolago harbour entrance is just visible in the distance. In the second world war it was protected by an anti-torpedo net. Shortly after midnight, the three canoes made this crossing, at 15-minute intervals, stealing their way to their targets.

Shrimp, after narrowly missing a boat of high-spirited sailors, was challenged from the shore. Thinking quickly, the canoeists replied, “Brandenburger Patrola”, pretending to be from a German unit. Then they were hailed again; rather than compromise their mission they paddled away and headed for Kalymnos.

Salmon, holed and filling with water, crept along the bay’s southern edge. They were challenged as well, but continued towards their destroyer, where men were standing on deck, so they waited in the shadows, baling silently. Eventually, they made the ship’s stern out of sight, and placed six magnetic charges.

Shark followed, placing explosives on three escort ships – despite voices and barking dogs nearby – and then closed on their main target, another destroyer.

Kos Atkis
Kos Atkis

The teams crept past the boom again at about 3am. Behind them the detonations confirmed their success.

Sunday 1200

I am in the spot they retreated to. On the sea-spattered rocks I can see a couple of indentations in which you could scramble up to high ground, but I cannot see anywhere to hide. Salmon made land after dawn; by afternoon they were discovered by a Greek fisherman, who kept silent despite the approach of a German patrol boat. After dark the three canoes paddled straight out from Kalymnos to their rendezvous with the caïque.

We head back to Panormos, surfing the swell for tens of metres. Three gruelling hours into the wind become just one when it’s at our back. An afternoon shower soothes the aching shoulders and then, after a last look at the angry and not-quite-conquered Aegean, I catch a flight to Athens. I wave goodbye to a smiling, and visibly relieved, Stefanos.

Sunday 1915


Lifting off from Athens, I fall into a sleep of Lethe, she being the Greek goddess of oblivion. My subconscious processes the whole adventure: the pleasure of the physical graft, excited wonder at battling a furious sea, relief at not flipping over – all tempered by frustration at the uncompleted plan. But on waking a single thought pierces the consciousness: I, at least, had the choice. On the Portolago raid, all three teams of canoeists may have made it back. But others didn’t.