Sailing Odysseus’s ancient route by superyacht

My dedication to recreating the Odyssey was nothing compared to Tim Severin’s, the writer who followed the route in the 1980s. He sailed in the Argo, a boat that approximated as closely as possible to Odysseus’s primitive craft. And in 1819, British writer William Goodison was even more daring, travelling around Ithaca’s coast in a flimsy copy of an ancient raft, built by a one-eyed local called Captain Odysseus.

But, still, even with the shortcomings of 13th-century BCE ocean travel, Odysseus’s black, tar-smeared ship should have managed the journey in a couple of months at most. Mediterranean ships were equipped with sails from around 2,500BCE; that gave ancient sailors 1,300 years or so to come up with some pretty quick yachts, before the Trojan War got going.

I spent an enjoyable afternoon, lying on my sunlounger at the hotel’s Bay View Beach restaurant, watching the beach being carefully reassembled. Just off shore, a dredger sucked up sand from the seabed and sent it back to the vanished beach’s rocky foundations via a huge, snaking, ribbed pipe. The sight of a beach being created in an afternoon was enough to make up for the whiff of briny sewage that accompanied the freshly dredged sand.

Still, when I got back to my boat, it was in pristine shape. Superyachts are well catered for on Mykonos – the charter company Mykonos Gold offers hundreds of yachts. The star of its range is the 17-cabin Christina O, Aristotle Onassis’s old yacht, named after his daughter.

But even the storm that hit my Mykonos hotel was nothing compared to the typhoons that blasted poor old Odysseus from side to side of the Mediterranean, like a demented wasp in a jam jar. However low my fortunes got on my trip, I was cushioned by technology, money and comfort.

And I was spoiled for choice when it came to restaurants. Every time you approach a Homeric site on your superyacht odyssey, you will find hoteliers and restaurateurs have got there before you.

I particularly liked the Maga Circe Hotel in Lazio, 80 kilometres south of Rome, and the Le Due Sirene Casa Vacanza near Positano. You will have the latest navigational equipment aboard, too. Odysseus only had the stars and the landscape. As I sailed into one harbour or another, I could see exactly why it was where it was.

So Istanbul, formerly the Roman city of Constantinople and, before that, the Greek city of Byzantium, is at the near-meeting point of Asia and Europe – with the Black Sea on one side, the Dardanelles the other and the Golden Horn to the west. It has just had a new port built in the heart of the city that can take yachts of any dimensions.

Dubrovnik is a peninsula stretched out in parallel to the coastline, forming its own natural harbour in the gap between the peninsula and the mainland. It, too, is perfectly designed to take superyachts. Some danger zones in the Odyssey were quiet as millponds when I recreated the trip. We sailed across the Strait of Messina, between the Italian mainland and Sicily, at dusk. As we approached Sicily, the sea couldn’t have been any calmer.

When I looked round Messina a few days later, I went in search of Charybdis, the deadly whirlpool that nearly sucked Odysseus to his death in the Odyssey. I didn’t see signs of any whirlpools in Messina Bay – which can comfortably house the biggest superyachts. Marina Messina is a deep-water harbour with no draught limit, right in the middle of town.

There is a yacht club, too, with clubhouse, bar and restaurant. The nearby Zancle 757 Yacht Village in Messina is a refit shipyard. I was later told by three sailors that earthquakes have shifted things around over the millennia, and that Charybdis lies further north along the Sicilian coast.

On the Italian mainland opposite Sicily, we dropped anchor later in flat-calm seas, by the restaurant-crammed hamlet of Scilla – wrapped around the rock on which Scilla the sea monster perched, grabbing Odysseus’s shipmates. Again and again, as I sailed round the Mediterranean in Odysseus’s wake, I came across the same places that he sailed to – or was shipwrecked on.

West of Messina lay the Aeolian Islands. Hidden by the hill of the horizon, they revealed themselves, one by one: Vulcano, Lipari, Salina, Filicudi, Alicudi, Panarea... and then there was Stromboli – like a child’s drawing of a volcano, an isosceles triangle with a scallop- shaped indentation at the top of the cone.

You can sail in a superyacht right next to the shore of Alicudi, examining the dramatic colours and scars in the rocks formed by the volcano. Continue on a few miles to anchor at Filicudi for lunch and a swim in empty, glass-clear waters.

If it’s shopping you’re after, anchor at nearby Panarea, with its picturesque stores lining the cobble-stoned streets. Thrill-seekers can snorkel or kayak through the rock tunnel at the tip of the nearby island of Dattilo.

If you wish to dine off the boat, the deck at the Hotel Raya is a fabulous sunset venue. The Italians love their fireworks, and you may be treated to a grand display celebrating a patron saint or any number of events.

Historians should sail to Lipari and its Aeolian Archaeological Museum – the best in the Aeolian Islands. These islands were ruled by Aeolus, god of the winds – hence the Aeolian harp, its strings plucked by the air.

In Book 10 of the Odyssey, Aeolus gave Odysseus a firmly sealed bag of winds so that, at last, he could sail back to his beloved home island of Ithaca and his wife, Penelope. Convinced the bag was full of riches, Odysseus’s men ripped it open, only to let loose the wind that sent them racing back towards Sicily.

West of the Aeolian Islands, 30 nautical miles north of Palermo, lies another claimant to the title of Aeolus’s royal island: Ustica. Once a prison island used by Mussolini to jail his enemies and by the Italian government to lock up Sicilian Mafiosi in the 1950s, Ustica is a wild, isolated speck of land.

Today, its harbour can comfortably house superyachts. And local guides can take you on underwater archaeological tours to view ancient Roman sites, stacked with amphorae (ancient storage jars). As we sailed into Ustica, the growing speck formed itself into two big humps – like a fat man lying in the water, one hump his head, the other his rounded belly, connected by a low neck of land.

The only big town, also called Ustica, trickles down the fat man’s neck to the harbour – a streak of orange roofs on an otherwise untouched island. Right on cue, as the twin humps swung into view, some modern Aeolus opened his bag of winds. The flat waters were instantly flecked with white horses, flanked on either side by deep barrel vaults of blue-black water, reflecting the angry, lowering heavens above. Still, we made it into Ustica in good time for dinner.

Odysseus would have recognised one landscape more than any other: his home island of Ithaca. Just as it is described in the Odyssey, Ithaca’s capital, Vathy, is securely tucked away from the winds. As soon as we turned into the main bay of Ithaca the brisk westerly wind dropped.

It was just like in the Odyssey, where two headlands “keep back the great waves raised by heavy winds without, but within the benched ships lie unmoored when they have reached the point of anchorage”. What’s more, Vathy has unusually deep water, ideal for large boats. It took its name from bathus, Greek for deep. (Greek “b”s are pronounced like “v”s.)

The most moving site of all on my voyage was Odysseus’s palace on Ithaca. Far below the peak on which the palace perches, I looked down on Frikes Bay – from phrikes, the Homeric word for ripples on the surface of the sea that were still rippling away.

A little further down the coast was Aphales Harbour, named after the Homeric term for white horses at sea – there they were, bucking away. The sea was the great name-giver in the Odyssey, even to the gods: Aphrodite was named after aphros, Greek for sea foam.

Towering over Ithaca, visible as we sailed in, is Mount Neriton: “Neriton with its trembling foliage,” as Homer called it.

I had a blissful evening swim in Phorcys Bay, where Odysseus was carried in a deep, exhausted sleep, by the friendly Phaeacians from nearby Corfu. It was late September, when the Mediterranean is at its warmest after a long summer of baking heat. Whenever I swam in the sea on my odyssey, I felt closest to the natural forces that have whipped those waters and shaped those coasts since Odysseus sailed there 3,000 years ago.

At these moments, I remembered Tennyson’s Ulysses. The poem pictured an ageing Odysseus on Ithaca, yearning to set sail again: “It may be we shall touch the Happy Isles / and see the great Achilles, whom we knew / Tho’ much is taken, much abides.”

The same still applies to Homer’s world – much has been taken, but an awful lot abides for the superyacht sailor.

Harry Mount is the author of Harry Mount’s Odyssey –Ancient Greece in the Footsteps of Odysseus (Bloomsbury)

First published in the March 2025 issue of BOAT International. Get this magazine sent straight to your door, or subscribe and never miss an issue.