Photo Credit: Adrien Sifre

After the fall of Troy, Odysseus and his men embarked on the perilous and unexpectedly long journey back to Ithaca, Greece. Along the way they faced monsters, battled cannibals, got played by the mischievous Gods, killed many, lost many, and circled the entire Mediterranean for 10 years – before arriving home, alone and garbed in rags.

Today, adventure seekers can recreate that legendary odyssey by motor or sailboat with relative ease (and in well under a decade). The route will take you to several key seaports on three different continents that snakes back and forth across the Mediterranean. There are many theories about which route the epic hero took exactly, but for the sake of travel, we recommend the route that visits as many Mediterranean hotspots as possible.

Traveling through the very setting that inspired Homer’s epic novel, The Odyssey, it is easy to see how the region could stimulate the imagination between fantastic islands ringed in picturesque beaches, commanding cliffs, bright blue waters, unforgettable sunrises and unimaginable sunsets. Embark on your own Odyssey following the footsteps of a literary hero.

Photo Credit: Darla دارلا Hueske

Troy – Along The Aegean Sea, West of Edremit, Turkey

The journey of several thousand miles starts at the legendary Trojan city in modern-day Turkey. Odysseus and his men had just finished the grueling Trojan War that saw the fall of Troy, and was the basis for Homer’s first work, The Illiad. Exhausted, and ready to return home to Greece, they set out, unknowingly to embark upon one of the greatest adventures ever known.

You can visit the ruins of Troy. They have been thoroughly weathered by the ages, but tourists can still see the stacked stones of the once towering walls of this [nearly] impenetrable city. It was one of the greatest sieges in history, and you can stand on the battlefields where Achilles, Paris and Hector fought and bled in the Trojan War.

Photo Credit: Christian Lendl

Across The Aegean Sea

Rather than sailing south around the Greek islands to Ithaca, their endpoint, the crew went North, stopping at the Island of Cicones to resupply.

Photo Credit: Dimitris Siskopoulos

Ismaros (Island of Cicones) – Eastern Greece

Odysseus and his jolly men stopped in at Ismaros to pillage the city, taking all the food, water and gold that was there. The gods were unhappy with their actions, thus beginning their plight.

Today Ismaros is in the eastern-most part of Greece, along the Aegean Sea. Alexandroupoli is a nearby port city where you can dock, check out the Alexandroupoli Lighthouse, and enjoy some fresh Greek seafood.

Photo Credit: Ingo Meironke

South Across The Mediterranean

Upon their departure from Ismaros, the much-smaller crew was blown drastically off course by fierce winds and ugly storms. They were driven south down the length of the Aegean Sea and then west across the Mediterranean to the Gulf of Gabes in modern day Tunisia, Africa.

Photo Credit: Jacqueline Poggi

Island of The Lotus Eaters – Gabes, Tunisia

It was in Tunisia where the team met the seemingly hospitable Lotus Eaters who shared their stupefying lotus-liquor with the sailors. The elixir drained the men of all desire to go home and nearly ended the journey altogether. But Odysseus realized this, and pig-tied his boys, tossing them aboard the ship before real disaster struck.

Gabes is a port city that has a lot of beautiful Muslim architecture and cool local markets. But if you want to see some truly remarkable African desert beaches that might drain you of all desire to leave, check out the nearby Island of Djerba.

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North Across The Mediterranean

When the crew departed the Island of the Lotus Eaters, they headed north, and landed back in Europe on the Island of Sicily, where they ran into a terrifying and unforeseen adversary…

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The Island of the Cyclops – Agrigento, Sicily

Sicily is as wonderful and relaxing as it is always described: temperate, beautiful and quintessentially Italian. But when Odysseus landed here he found it ominous and unsettling. Captured by the Cyclops known as Polyphemus, four men were eaten alive before they managed to escape.

Sicily doesn’t have a Cyclops problem any more, so you are more than welcome to dock your boat and explore. Agrigento is a hilltop city sporting a valley full of exquisite Greek temples and the ruins of the ancient city of Agrakas. Or head to Riserva Naturale di Punta Bianca, a beautiful nature reserve full of rolling coastal hills and sea life.

Photo Credit: Diana Robinson

Southwest Across The Mediterranean

The boys departed the Island of the Cyclops in a hurry, not paying a whole lot of attention to their course. They sailed due west away from their destination landing on yet another island.

Photo Credit: Gino Roncaglia

Aeolia (The Island of Aeolus) – Pantelleria, Italy

Legend has it that wind god, Aeolia, showed great hospitality to the Greeks and gifted Odysseus a bag full of the Westward winds – which was to remain closed until they reached Ithaca. Unfortunately, Odysseus’ jealous men opened the bag, convinced their leader was secretly hoarding gold and silver. The winds were unleashed and they were blown far off course.

The tiny volcanic outcrop is still Sicily’s largest offshore island, and is the picture of relaxation. The jagged lava-stone and caper bush blankets make for a spectacular backdrop for snorkeling and scuba diving (although there are no true beaches). There is also a magnificent natural arch that extends far into the sea, which is a popular photo stop.

Photo Credit: Christian Lendl

West Along Africa’s Northern Coast

They were blown back to Africa, traveling westward along the coast until they reached a place known as Telepylus – the stronghold of king of the Laestrygonians, King Lamos.

Photo Credit: Hichem Merouche

Telepylus (The Island of Laestrygonians) – Northeast Algeria, Between Skikda and Filfilla

Upon arriving, the Greeks sent several men ashore to scout the area, one of whom was eaten by the cannibalistic Laestrygonians. As the remaining crew fled for the ships, the natives pummeled them with boulders, smashing several of the boats and killing hundreds of men.

Today, you'll find a peaceful, thriving port city. Skikda isn’t really known for it's tourism – so many may choose to continue onwards. If you do wish to explore, the Abazza theater features local music, and the Collo and Skikda Beaches are a nice place to chill and soak in some Algerian rays.

Photo Credit: Patrick Nouhailler

North Across The Mediterranean

Fleeing Telepylus in a hurry, the men sailed northwest towards modern day Spain.

Photo Credit: Iñaki Pérez de Albéniz

Aeaea (Circe’s Island) – Palma, Baleric Islands, Spain

It was here, on Circe’s island that Odysseus’ luck turned for the better… at least, for a little while. The beautiful goddess of magic, Circe, tricked half of Odysseus’ men into drinking poisoned wine that turned them into pigs. She fell in love with Odysseus (immune to her magic) and demanded he make love to her. Odysseus, the sly dog that he was, negotiated the re-transformation of his swine-bretheren back into humans before allowing Circe to have her way with him. He stayed for a full year, feasting with his crewmates and enjoying the romantic rendezvous, before nobly deciding it was time to return to his wife.

Modern day Palma is one of the most relaxing and beautiful beach resorts in the Mediterranean. Gorgeous vistas are available across the island, and the architecture is distinctly Moorish in style. There are a ton of historical monuments, cathedrals, market places, and hiking trails ripe for exploration. Even without the spectacular cuisine of this region, Palma would still be a highly sought after destination, but the fresh Spanish seafood dishes of this land are renowned worldwide for their distinct flavor and spices.

Photo Credit: Tuquetu

West to Spain Proper

Once Odysseus determined it was time to return to his family, Cerci gave him a lot of advice and convinced him to make a quick pit stop in the Underworld to find the prophet known as Tiresias. The prophet, she said, could tell Odysseus how to get home.

Photo Credit: Juan Mercader

The Underworld (Land of the Dead) – Valencia, Spain

While it sounded easy enough in The Odyssey, there is no known way to sail to the underworld. Instead, the southern villages of mainland Spain is only a hop and a skip from Palma. Picturesque, vibrant and suffused with excellent food, wine and music, it's not hard to feel gluttonous and sinful. Try a big bowl of paella, spiced with locally grown saffron and cooked with locally caught shellfish.

Photo Credit: bestfor / richard

East Across The Mediterranean

After our hero made his lonesome trip into the underworld, he returned to his crew alive and successful. He had found the prophet Tiresias, who advised him how to appease the gods so they would allow him at long last return home. Off they sailed, east this time, prepared for whatever obstacles may come their way.

Photo Credit: Alessandra Argiolas

The Island of the Sirens – Cagliari, Sardegna

When they reached the Island of the Siren’s (southern Sardegna) upon recommendation from Circe, Odysseus filled his crew’s ears with beeswax, so they wouldn’t fall victim to the irresistible sound. Tying himself to the mast of the ship so he could hear the Sirens’ song, he writhed, begged, and pleaded to let them pass. Successful, they continued on.

Sardegna’s southern coast is an amazing place. Cagliari (literally meaning “castle”) is the closest location to the fabled Siren Island. This port town is full of colorful buildings and golden-hued domes, the centerpiece being Il Castello, a citadel that stands watch over the city. The architecture and culture is distinctly different than Italy's mainland so take a few days to enjoy the vivid and historical ambience.

Photo Credit: Canon

East Across The Mediterranean

They continued east toward modern day Messina, but their course took them through an extremely dangerous strait.They would have to pass between two cliffs, both monitored by deadly mythological beasts: Scylla and Charybdis.

Photo Credit: Marco Crupi

Scylla and Charybdis – Messina, Sicily

Scylla was a giant six headed beast that lived on the cliff directly across from Charybdis, an underwater monster that would swim up from beneath and swallow ships whole. Weighing the options, Odysseus decided to pass by Scylla and sacrifice six men instead of potentially losing the entire ship.

Messina is an important gateway to and from the island of Sicily, and it has been a strategic transportation hub throughout history. The narrow strait dividing Sicily from the mainland is very thin, and is the setting for the Scylla and Charybdis encounter. Messina is a big, bustling city, plagued by traffic, but it is full of poignant monuments and cathedrals.

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South Across The Mediterranean

Continuing south, the crew of weary adventurers stopped on the island of the sun god himself: Helios.

Photo Credit: Giuseppe Milo

The Island of Helios – Malta

When the crew stepped ashore they noticed an abundance of cattle on the island. But Odysseus had been warned about these tasty looking bovines: they belonged to Helios, and he loved them very much. So Odysseus sternly commanded that no one touch the cows. The winds were violent, though, and the men were stuck on the island for over a month, driven to such hunger that they broke down and ate one of Helios’ cows.

Throughout its lengthy history, Malta has been ruled by the Romans, the Moors, the Knights of St. John, the British, and the French. As such, the culture is extremely rich and varied, with plenty of well-preserved historic sites. There are numerous fortresses, megalithic temples and even a subterranean complex of halls and burial chambers as old as 3600 BC.

Photo Credit: Dave Price

West (ALL THE WAY) Across The Mediterranean

Suffice it to say, Helios was upset by the consumption of his sacred cattle. When the crew left his island, their ship was sunk by of terrific storm and every crew member save Odysseus was sucked into and eaten by the Charybdis. Odysseus drifted at sea for a long time, before washing ashore several hundred miles west.

Photo Credit: Antonio Pavon

Ogygia (Calypso’s Island) – Ibiza, Baleric Islands, Spain

Much to Odysseus’ dismay, the beautiful nymph Calypso (modern Ibiza in the Baleric Islands) made him her lover for seven years until finally, Athena stepped in and forced Calypso to let him go, determined to return to his wife and son.

Fortunately for tourists today, Ibiza is one of the most beautiful vacation destinations in the Mediterranean. Quiet villages, sandy coves, and fragrant pine forests are contrasted with the lively, world renowned nightlife.The bars and clubs are always rowdy, but if you'd prefer to enjoy a beer on the beach, no one will stop you.

Photo Credit: SoniaDee

West Across The Mediterranean

Alone now, our hero made his way east – past Circe’s island (Palma) – on a raft provisioned with food, wine and water. But the legendary sailor was once again foiled by a storm that destroyed his raft and drifted ashore on the Island of the Phaeacians.

Photo Credit: Christoph Sammer

Sheria (Island of The Phaeaians) – Santa Teresa Gallura, Sardegna

When Odysseus awoke, he was surrounded by naked women, bathing and playing ball. One was the daughter of the King and Queen. The girl, Nausica, fell in love with Odysseus, the ragged adventurer. But before she could marry him, Odysseus was painfully reminded of the Trojan horse by a blind bard, and resolved to finish his journey to Ithaca.

The north Island of Sardegna is equally as beautiful as the south (where the sirens made their attempt to lustfully lure Odysseus off-course). The small coastal city of Santa Teresa di Gallura is situated on some of Sardegna’s most pristine beachfront. Despite big crowds during the high season, this small Italian town retains its local flavor. Relax on the beach and listen to the unique Italian/Corsican dialect spoken by the locals. It is also a good place to get underwater and see some aquatic life by scuba or snorkel.

Photo Credit: Tyler Karaszewski

West Across The Mediterranean, Around The Tip of Italy

The final stretch of the odyssey was covered in a boat offered by Nausica’s father when he heard the hero’s unbelievable tale. He was outfitted with proper gear and supplies, and sent east, towards home.

Photo Credit: Zhang Yu

Ithaca, Greece

When he finally arrived at home, Odysseus did as any nobleman who had been gone for ten years would do, and disguised himself as a beggar to confirm that his wife, Penelope, had remained loyal...killing all her suitors to live happily ever after.

Ithaca is still a harbor city, just off of the Ionian Sea. It is a small town, with a very local Greek feel. Sailboats and motorboats come in and out lazily through the summer months, relatively undiscovered by the masses. There is plenty of hiking on the island, and even some great mountain biking tails. The scuba diving is world-class and the beaches are the perfect place to rest your weary body.

An adventure on the scale of Odysseus’ is no easy or small undertaking. It requires courage, and planning, and knowledge of sailing and weather. There are few people alive who could recreate such a massive journey, but to those brave souls who dare to dream we say "try it."