6 ways to experience Homer’s Odyssey by luxury yacht

The distance from Troy, now Truva, in Turkey, to the Ionian island of Ithaca is only about 550 nautical miles. Yet after the Trojan War it took the ancient Greek warrior Odysseus 10 years to find his way home to wife Penelope, west across the Mediterranean. It was a voyage on which, as Homer’s opening paragraph puts it, “he suffered great anguish on the high seas”.

The Odyssey is not, then, an obvious book on which to base a cruising itinerary. For a start it’s fiction and the geography in it is essentially invented. Focus your route, however, on the places believed to have inspired the islands in the heart of the poem (books nine to 12), which are mostly in the Tyrrhenian Sea, west of the Italian mainland, and Homer’s epic has the potential to inspire and inform a Mediterranean superyacht charter that appeals to the most discerning lotus-eater.

Mljet, Croatia

The saga starts on the island of Ogygia, home of the nymph Calypso, on which she holds Odysseus prisoner. Several places lay claim to having been the model for Ogygia, not least Gozo off the coast of Malta, and Mljet, off Croatia’s Dalmatian coast. Who knows if there’s truth in either, but Homer’s descriptions of the extraordinary “vaulted cavern” in which Odysseus is forced “to sleep with her, cold lover, ardent lady”, the fragrant landscape of cypress, cedar, alder, juniper and vines, not to mention the abundant red wine produced from them, chime with the reality of modern Mljet.

It is an idyllic place, much of it a forest-cloaked national park with two small salt lakes, one containing an island with a 12th century Romanesque monastery. Mljet is well worth an overnight stop if you are sailing in the Adriatic north out of Porto Montenegro or Dubrovnik, or south from Split. It is on Mljet that Odysseus’s prayers are finally heard on Mount Olympus and he’s allowed to escape. From then on the story, told mostly in flashback, is a familiar one. Leaving Troy, Odysseus and his flotilla are “wafted” north toward Thrace – now around the borders of eastern Greece, Bulgaria and Turkey – and Ismarus, “the city of the Cicones”. His behaviour there is not exemplary. “I sacked this place and destroyed its menfolk,” he later relates to Alcinous, king of the Phaeacians. “The women and the vast plunder that we took from the town we divided so that no one, as far as I could help it, should go short of his proper share. And then I said we must escape with all possible speed.”

Need to know: With calm, secluded waters, Mljet offers some of the most idyllic anchorages in the secret islands of Croatia. The village of Polae has a wealth of ancient ruins, including a Roman palace.

At Odysseus’s next port, in Sicily, they encounter the cannibalistic one-eyed Cyclops. Off the coast of the village of Aci Trezza, three giant rocks emerge from the sea, now known as I Araglioni dei Ciclopi; these are “great pinnacles” torn from the mountain and hurled by Cyclops leader Polyphemus at Odysseus’s “black ship” – probably a 50-oared penteconter – as he fled the island.

Need to know: The landmark for a history packed cruise on luxury yacht in Sicily. Begin at Marina di Riposto, for visiting Mount Etna and Catania, crawl south west to the medieval and Baroque architecture of Syracuse, ogle Phoenician artefacts in the Museo Archeologico Baglio Anselmi or sip sweet wine in Marsala, explore grottos in Trapani, stop off at the capital Palermo and finish with the Cathedral at Cefalu.

Odysseus’s next stop is likely the Aeolian Islands, a seven-island archipelago north of Sicily that includes Stromboli, Vulcano, super-fashionable Panarea (the place to anchor for nightlife) and Filicudi. The latter, though scarcely developed, offers some of the best diving in the Mediterranean, thanks to its limpid waters and spectacular underwater rock formations and grottos, especially if you anchor between La Canna, a massive spiralling lava spike, and the Scoglio di Montenassari, a great flat-topped cliff that rises from the seabed.

This area is one of the loveliest cruising grounds in the Med and, if you’re under sail, one of the fastest. Named after Aeolus, god of the winds, at times all the turbulent air in the world seems to converge tempestuously on this spot, while at others it can be still and hot. . No surprise then that Aeolus’s gift to Odysseus was a bag of winds to ensure he would not be blown off course.

Need to know: Although the islands do not have a marina big enough to support superyachts, pretty anchorages are in plentiful supply (and because there are no flights – apart from helicopters – you are likely to enjoy them in peace). Lipari has a wild, rugged coastline; more developed Salina offers boutiques; and if you have nerves worthy of a classical hero, on Stromboli you can climb an active volcano. Zimmari is a secure anchorage in Panarea with great diving.

Odysseus’ impatient crew, thinking that their sails might benefit from the extra wind power, open the Aeolus’s gifted bag of wind, unleashing a storm that blows them further off course north to the land of the boulder-hurling, man-eating Laestrygonians – what is probably Bonifacio on Corsica. “An excellent harbour,” wrote Homer, “closed in all sides by an unbroken ring of precipitous cliffs, with two jutting headlands facing each other at the mouth so as to leave only a narrow channel between.” Which is exactly as it remains.

Need to know: Port de Plaisance de Bonifacio, one of the most dramatic marinas in the Med, nestles beneath the towering cliffs of the town. Facilities are limited to electricity, water, pump-out and WiFi, but it’s only a short walk up into the town. There are also multiple beautiful superyacht anchorages in Corsica.

Odysseus then heads north to Aeaea, home of the “formidable goddess” Circe. Some hold that this is the island of Ponza, one of the Pontine Islands, which lie 22 nautical miles off Lazio, south of Rome. Arriving on this alluring speck of an island, Odysseus and the rest of his dwindling party “lay on the beach for two days and nights”. And no wonder, for its beaches and the clear waters that lap them make this a popular place to anchor. It’s also a good place to dive, once a favourite of Jacques Cousteau no less, and a location in Wes Anderson’s The Life Aquatic with Steve Zissou. On the west of the island, Chiaia di Luna is a spectacular stretch of sand (although currently closed because of a danger from falling rocks) where the aquamarine water deepens through emerald to a true sapphire blue as it nears the horizon.

Defined by its towering cliffs, Ponza is best appreciated from the water. Many of its loveliest bays and most secluded coves are accessible only by boat, as are its neighbouring islands, their coastlines scalloped by grottos. All are uninhabited except for Palmarola and Ventotene, where six years ago marine archaeologists discovered five ancient Roman ships with their cargoes – amphorae of olive oil, garum (a fermented fish sauce), metal ingots – still largely intact.

Need to know: The island boasts Egyptian, Greek, Canaanite and Phoenician ruins. Take a tender to explore the numerous coves, grottos and tiny beaches that dot the island – chances are you’ll find a spot all to yourself – then return for sunset when the cliffs glow orange, pink and red. The closest yachting services are at Marina Molo Luise, in Naples and about 10 miles’ drive from the international airport.

Next come the Sirens, the bewitching creatures – birds with human heads – whose music is so seductive that men abandon everything just to stay within earshot. They gave their name to Le Sirenuse, a little three-island archipelago off the Amalfi coast near Capri, which belonged to the dancer Rudolf Nureyev from 1988 until his death in 1993. He hired architect Le Corbusier to build him a villa and replanted its terraces with vines. Still in private hands, the largest island, Gallo Lungo (or Amalfi Island as it’s been rebranded) can be rented from €130,000 a week, via vladi-private-islands.de.

Odysseus steered clear of Le Sirenuse, having himself bound to the mast of his ship and insisting his men block their ears with wax to resist the Sirens’ call.

Need to know: In such established superyacht territory, staying on board is seriously convenient. Marina di Capri lies within a protective breakwater in the heart of town near a wealth of romantic restaurants and glamorous bars.