My very own Greek Odyssey: a sailing trip to the island of Ithaca

The steep climb up the hill behind is not easy, a formidable barrier of rugged terrain that underscores the isolation of this spot. I skirt thick clumps of thorn, their sharp defenses guarding the land, and weave through gnarled, abandoned ancient olive trees, their silvery leaves whispering secrets of past cultivation and lives lived. These venerable trees, some possibly hundreds of years old, stand as silent sentinels, their twisted trunks bearing witness to generations of human endeavor and eventual departure. Scrambling over jagged outcrops of white limestone, the geology of the Ionian coastline reveals itself – dramatic, karstic formations sculpted by millennia of wind and water. Every time I curl my fingers into a rocky niche for purchase, a primal fear surfaces, and I think about snakes, though the reality of encountering one is slim, particularly in such exposed conditions. The only residents, however, are spiders, architects of intricate, ephemeral empires. Their webs are strung between the trees, glinting like gossamer nets in the sunlight, and so thick and strong that I grab a stick to slash through them, a minor act of disruption in a place where no one has been for a long time, suggesting a profound sense of forgotten history and undisturbed nature.

Near the hilltop, the landscape abruptly shifts, and I stumble on a ruined stone building, its crumbling walls hinting at a past existence. Who lived here, I wonder? And where have they gone? Was it a shepherd’s shelter, a farmer’s humble dwelling, or perhaps a lookout post guarding ancient sea lanes? The silence offers no answers, only a poignant sense of transience. A few steps further, and the land abruptly ends in a vertical white cliff that plummets into an improbably blue sea, a breathtaking vista that steals the breath and demands contemplation. The sheer drop, a dramatic geological punctuation mark, frames the vast expanse of the Ionian. Far away, in the haze of the Mediterranean summer, there is a stack of Ionian islands – a faint, ethereal outline on the horizon. And one of them, I know, must be Ithaca, the legendary home of Odysseus, drawing me into its timeless narrative.

At that moment, a sudden, unexpected sensation shatters the poetic reverie: I feel footsteps running across my forehead and let out an involuntary scream. An arachnid Achilles, disturbed by my intrusion, has come to take revenge, its tiny legs a terrifying drumbeat on my skin. I leap up, arms flailing in a comical, desperate dance. The eight-legged hero, perhaps seeking refuge or merely confused, heads for the underworld of my left armpit, a sudden, close encounter that jolts me back to the immediate, sometimes absurd, reality of travel.

This abrupt plunge into personal chaos, though trivial, perfectly embodies the literary device of in media res, a narrative technique where the action starts in the middle of the story, a rule first identified by the Roman poet Horace in his Ars Poetica. At that central moment, our protagonist is typically in a terrible state: probably lost at sea, often naked, and always alone. This deliberate narrative choice immediately hooks the audience, prompting the essential questions: how did things get to this nadir, and where will they go now? It’s a pattern repeated over and over in Western literature and cinema, from the epic struggles of ancient heroes to the amnesiac quests of modern protagonists. Take, for example, that ancient classic The Bourne Identity, a 2002 film starring Matt Damon, who appears in the opening sequences floating in the Med like a stunned octopus, adrift and disoriented. He doesn’t even know who he is, his past erased, yet with the hospitality of strangers and cathartic bouts of extreme violence, he inches towards his happy place – a journey of self-discovery through peril, much like Odysseus’s own arduous voyage home.

Now, in a fascinating hypothetical twist that blurs the lines between ancient epic and modern blockbuster, Matt Damon gets to do it all again, but this time in a pleated skirt and bronze helmet, appearing as Odysseus in Christopher Nolan’s The Odyssey, a fictional $250m blockbuster due for release on 17 July in the UK and US and starring almost every deity in the Hollywood heavens. This imagined film would undoubtedly present a streamlined, action-packed version of the epic, focusing on spectacle and heroism. However, if one goes back to the literary Odysseus (with Emily Wilson’s brilliant recent translation offering fresh insight into his complex character), he is much more than a Hollywood action hero. This home-loving husband, yearning for his wife Penelope and son Telemachus, is also a pathological liar, a master of disguise, a serial philanderer, a ruthless murderer when necessary, a skilled carpenter, and, most famously, a traveller. And like all travellers, especially those recounting extraordinary adventures, sitting around the campfire at some later date with listeners agog, he is forced to confront the thorny problem of how to convey the full visceral impact of what happened on his journey and hold his audience spellbound. Traditionally, there are two options for such a storyteller: the full truth, or the fuller truth – a truth embellished just enough to capture the wonder, the terror, and the sheer improbability of his experiences.

Back on the clifftop, tickled to death by Achilles and momentarily disoriented, I dive into the improbably blue sea, seeking escape and refreshment. Only then do I find that my assailant, the tiny spider, has transmuted into a six-headed monster that’s dragging me towards a giant whirlpool – a vivid, almost hallucinatory echo of Scylla and Charybdis, the mythical perils faced by Odysseus himself. And, in a far more mundane but equally frustrating twist, I’ve lost my glasses in the process, adding a touch of modern inconvenience to the ancient struggle.

My actual journey began a few days earlier, when I had come to the Greek mainland and set sail for Ithaca. This endeavor is actually easier than it might seem, thanks to modern tourism infrastructure. First, one must track down a friend with the correct sailing credentials, such as an RYA (Royal Yachting Association) qualification, or pursue them yourself through dedicated courses. Then, gather a capable crew and search out a suitable boat for charter. Alternatively, for those less experienced or simply desiring a more relaxed voyage, paying the extra to hire a professional skipper is a wise choice. We chose to sail with Neilson Holidays, a reputable operator which has a mainland base near Palairos on the Ionian Sea. Depending on experience and qualifications, you can either follow a flotilla – a group of boats sailing together with lead crew support – or go it alone on a bareboat charter. The Neilson support crew proved to be our secret weapon in finding the right adventures: their local knowledge was invaluable. They knew every cove and cave in the region, every hidden taverna, and were quick to share their insights, transforming a mere sailing trip into an authentic exploration. We arrived and found our boat, named Cafard, which my multilingual skipper friend, Fabian, rather wryly translated as "Depressed Cockroach." I couldn’t help but wonder if it was a misspelling, or perhaps a clever, melancholic nod, to Cavafy (Constantine P), the great Alexandrian Greek poet who wrote the iconic poem "Ithaca," which begins:

When you set out for Ithaca
Ask that your way be long,
Full of adventure, full of instruction.

Cavafy’s poem, a timeless meditation on the value of the journey over the destination, perfectly encapsulated our hopes for the voyage. It was a poignant reminder that the true treasure of such a trip lies not merely in reaching the fabled island, but in the experiences, lessons, and transformations encountered along the way. We stocked up on provisions – local olives, fresh bread, crisp Greek wines – and set sail. Adventure and instruction were indeed our hope. My wife, Sophie, had never sailed before and was scoffing seasickness tablets faster than Odysseus’s men gobbled down the sun god’s sacred cattle, a transgression that, in the epic, did not end well. Could we, despite the modern conveniences and the inherent risks of a first-time sailor, discover a Homeric sense of wonder and novelty on our voyage to Ithaca? And, perhaps more importantly, could we report back truthfully, without succumbing to the temptation of the "fuller truth"?

Despite the yacht name, the beginning of our voyage was auspicious. Leaving Palairos, a charming coastal town serving as a gateway to the Ionian, we sailed into a pod of dolphins, their sleek bodies arching gracefully through the waves, swarming around the bows of Cafard. They were close enough to make eye contact, a magical encounter that felt like a blessing from Poseidon himself. That night was spent on Kalamos, a steep-sided, densely wooded island with a tiny, picturesque port. Its dramatic topography and lush vegetation are typical of the less developed Ionian islands, offering a tranquil escape. In the taverna, a quintessentially Greek scene unfolded: sleepy cats stretched out under chairs where old men, their faces etched with the wisdom of the sea, were making a single glass of ouzo stretch out too, savoring each sip and the slow rhythm of the evening. There was talk, a whispered local legend, of a crashed military drone found by fishermen in a sea cave north of here. The engine was still running, they claimed, and there were 100kg of explosives on board. Is this story also getting stretched a little, I wonder, a modern echo of ancient myth-making? Or is it connected to the whispered presence of "unfriendly Russians" on some islands, hiding behind warning signs for savage dogs – a contemporary paranoia woven into the fabric of local gossip? Odysseus, ever vigilant against affronts to hospitality and threats to his domain, would certainly not like that. He was fine-tuned to any abuse of hospitality, and perhaps a tad oversensitive when it came to other men flirting with his wife, a trait that often led to dramatic, and violent, confrontations.

The next morning we sailed out, leaving Kalamos behind, stopping briefly at Porto Leone, a village on Kalamos abandoned after the devastating 1953 Ionian earthquake. This cataclysmic event, measuring 7.2 on the Richter scale, reshaped the islands of Kefalonia, Zakynthos, and Ithaca, causing widespread destruction and prompting significant depopulation as many residents emigrated. Porto Leone stands as a poignant reminder of this seismic tragedy, its silent ruins speaking volumes of lives disrupted. The original plan was to stop again at the island of Atokos, a largely uninhabited gem where wild pigs reputedly swim off the beach, a testament to its untouched nature. However, the wind picked up, and we found ourselves properly smashing through the waves, the boat heeling over in exhilarating fashion. Fabian, the seasoned skipper, was loving it, his face alight with the thrill of the open sea. Sophie, to her amazement, felt no seasickness and was letting out shrieks of pure joy, her initial trepidation replaced by the sheer delight of the journey.

We then set our course for Kioni on Ithaca, a village little more than a scattering of old houses clustered around an exquisite, horseshoe-shaped harbour. In August, I’m told by locals, the berths are all taken before lunchtime, a testament to its popularity among the yachting crowd. The waterfront is a lovely mix of tradition and modern charm: a corner shop that stocks everything from fresh produce to boat supplies, a top-notch bakery filling the air with the scent of warm bread, authentic tavernas serving fresh seafood, and some swish boutiques catering to the discerning traveler, all tied together with vibrant, colourful plumes of bougainvillaea. In one particularly arty studio, a yachtie with auburn hair and a regal manner was demanding the price of a striking swordfish sculpture. "It’s €15,000," purred the assistant, a price tag that speaks to the high-end tourism also present here. Not everything is so pricey, thankfully: we found that a good dinner with wine, featuring local specialties like fresh grilled octopus or pastitsio, could be had for less than €25 each, proving that authentic Greek experiences remain accessible.

The next day, I ventured out to walk some of the island’s footpaths, a network that badly needs a strimmer, their overgrown state adding to the sense of wild, untamed beauty. In the town of Stavros, nestled in the northern part of the island, the tiny archaeological museum holds an astonishing array of Homeric treasure that was found in a nearby cave. Among the most remarkable artifacts is a second-century BC shard of pottery bearing the inscription "pray to Odysseus," strong evidence suggesting the hero was venerated as a local deity or cult figure. The museum also houses several pieces of bronze tripod cauldron dated to the ninth century BC, items that in local minds are confidently identified as some of the Phaeacian gifts mentioned in The Odyssey – the lavish treasures bestowed upon Odysseus by King Alcinous and Queen Arete to aid his return home. This tangible link to the epic powerfully blurs the lines between myth and history, fueling the island’s unique identity.

A mile further up the trail, at a site known as the School of Homer, lie the ruins of what may have been a palace – though archaeological consensus is still out on its definitive identification as Odysseus’s abode. Nevertheless, this tantalizing possibility is sufficient evidence for locals to build a model in Stavros town square and confidently identify the bedroom of Odysseus, complete with its olive tree bed. Listen closely, and you can almost hear him, the master of plausible deniability, spinning tales to his long-suffering wife: "Honestly Penelope, they both bewitched me. Calypso and Circe, they were goddesses! I was a sex slave. I couldn’t wait to get home." The tradition of Odyssean tall tale-telling, it seems, is in robust good health, enduring through millennia. In the highly recommended Margarita Cafe in Stavros, there is another fine tradition on display: cakes. The local speciality is rovani, a delicious spicy concoction made with rice flour, honey, and cinnamon, served warm with a scoop of vanilla ice-cream – a sweet, comforting taste of Ithacan hospitality after a day of Homeric exploration.

Our broader voyage took us past the majestic shores of Kefalonia, the largest of the Ionian Islands, and to the bustling, sometimes noisy mainland port of Sivota, a popular hub for yachting and tourism. But after a valuable tip-off from Amy in the Neilson support crew, the true highlight came with that lonely anchorage off the mysterious island of Meganisi. While parts of the Ionian coast are undergoing a building boom – with glass and concrete palaces spreading across the hillsides like a nasty rash, threatening the region’s natural charm – Meganisi still retains pockets of unspoiled tranquility. Here, away from the crowds, we found solace: snorkeling through shoals of iridescent fish in crystal-clear waters, exploring vast, echoing sea caves carved by the elements over eons, and raising a heartfelt toast to that magnificent poet Homer, and the boundless inspiration he has given to so many for almost three millennia. His stories, born in these very waters, continue to shape our understanding of heroism, resilience, and the eternal quest for home. After a week on the water, filled with both epic echoes and personal adventures, we sailed back to Palairos. We had all had a great time, even the nervous first-time mariner, Sophie, who had found her sea legs and a newfound joy in sailing. I left with vivid memories, not least that desperate underwater struggle with the deadly spider woman who stole my glasses, a final, absurd echo of the mythical perils that continue to haunt these ancient, enchanting seas.

The trip was provided by Neilson Holidays: a seven-day South Ionian flotilla cruise from £595pp (for four adults) including flights from Gatwick; a skippered boat from £1,145pp. Adding a paddleboard is highly recommended for exploring secluded coves and caves (£85). Travel to London was provided by LNER, offering a comfortable journey to the capital, and accommodation for a pre-trip visit to the British Museum’s Ancient Greece section was generously provided by Radisson Blu Bloomsbury, allowing for invaluable historical context before embarking on our own Odyssean journey.