A scenic view of the beach beneath Castello Ruffo di Scilla in Calabria, Italy, with colorful houses lining the waterfront.

The Odyssey: a Jack's-Style Epic Itinerary

Will Stornbrook

Will Stornbrook

Updated:
4 min read

Christopher Nolan's The Odyssey is out, and it is a hit! 

Haven't seen it yet? I’d recommend you head to the IMAX ASAP. Already seen it? No one is stopping you from going again.

If you're feeling inspired to embark on your own odyssey, I’m going to guide you through a legendary adventure that will take in some of the most significant spots Odysseus and his crew encountered along the way. So, take this as your starting point — if we dove deep into every location, this article would be nearly as long as Homer’s epic poem!

Potential spoilers ahead. Although the book has been out for a while now…

Fair warning, this itinerary is pretty vast — you can see why it took 10 years for the Greek hero to get home! I’ve split it into two parts, starting with a larger quest encompassing the Aegean Sea and North Africa, and a smaller (yet still sizeable) journey across the West-Central Mediterranean. Pick and choose your stops as you see fit!

Note: Although these historical locations are disputed (if the mythical places exist at all), we’ve gone with the general consensus.

A large wooden structure resembling the Trojan Horse stands against a bright blue sky in Çanakkale, Turkey.

The Great Adventure:

Fans of archaeology and Brad Pitt rejoice, as the beginning of our story takes us to ancient Troy. Catch a flight to Çanakkale in Türkiye and head south to ramble through the ruins of the iconic sacked city. But don't skip the modern port of Çanakkale either, as it features an impressive 40-foot tall replica of a Trojan Horse!

Once you’ve got your antiquity fix, drive north into modern-day Greece to Maroneia, and treat yourself to a little more! Be sure to schedule in plenty of time post-ancient-city wandering for a bottle case of the very wine that Odysseus used to blind the Cyclops (no guarantees that you’ll be able to find the exact same vintage).

Then it’s time to grab a flight to Djerba, Tunisia. While it may have been the delicious (narcotic) lotus fruit that kept Odysseus’ men on the island, it’ll probably be the delicious pastries and truly idyllic beaches that make you never want to leave.

A stunning sunset over Djerba beach in Tunisia, with palm trees silhouetted against the colorful horizon.

But if you do manage to peel yourself away from the delightfully peaceful North African shores…

A Hero’s (more manageable) Expedition:

The next part of our quest will take you to the Ionian and Tyrrhenian seas. Fly to Sicily, where the myth-inspiring Cyclopean Isles near Catania serve as a fierce reminder of one-eyed Polyphemus's rage against a deceptive Odysseus (Nobody is to blame for that one). Then, following in the footsteps of the Greek legend, the Aeolian Islands are an excellent stop for some R&R — and only a ferry ride away. 

Before making for the mainland, you’ll head back to Sicily to sample the local cuisine in the town of Trapani. Fortunately, it’s mostly populated by seafood couscous-eating locals nowadays, instead of man-eating giants.

After a full belly (you, not the giants), touch down in Rome with a non-stop flight from Trapani and set sail to Ponza, where Circe’s enchanting grottos await (with no recent reports of sailors being turned into pigs). Then it’s a mainland excursion to Hades’ underworld crib near Cumae.

Small blue boats float on crystal-clear waters near the historic coastal buildings of Trapani, Sicily.

Once you’re done dicing with death, pack your earplugs and be wary of any siren song, as it's off to the entrancing Li Galli off the Amalfi Coast. These days, it’s less about washed-up sailors lured to their demise and more about influencers lured in by the promise of shimmering, crystal-clear waters.

Next, you’re making your way south to Calabria and the Strait of Messina, where monsters lurk high on cliffs and in the deepest waters…and in sandwiches. Bonus points if you divert away from the beachfront and make the climb up to Scilla Castle, where you can do some monster spotting from above.

Back over in Sicily, embrace the warming sun on the Island of Helios (just don't eat the beef without asking), before a voyage to Malta. It’ll be tough, but you must try not to spend the next seven years enamoured by Calypso's Island.

A scenic view of the beach beneath Castello Ruffo di Scilla in Calabria, Italy, with colorful houses lining the waterfront.

Catch a flight to Corfu and pick up a gift or two from the friendly locals (The Detour Editor Katy recommends the kumquat liqueur), before finally setting sail to Ithaca. This is where our Homeric myth comes to an end — as long as you’re not made to shoot an arrow through some axe heads.

Sadly, your odyssey is now over (unless you take a page out of Penelope’s book and make it last forever by unravelling your knitting project). The flight from Ithaca's closest airport in Cephalonia will see you home after this epic voyage. 

Of course, you could always tick off a few spots from Captain Corelli’s Mandolin before you jet off…

A picturesque view of the colorful village of Assos on the island of Kefalonia, Greece, nestled by a tranquil bay.
Will Stornbrook

Will is on a mission to eat the best burger ever. Using his base in London, he's exploring every historical nook and far-flung cranny to find it. When he isn't, you'll usually spot him exploring a new world in a book or video game. Sometimes he also falls ungracefully from climbing walls. Very occasionally he writes (when he isn't daydreaming about burgers...).

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