The Peloponnese peninsula is the jaw-dropping setting for Christopher Nolan’s eagerly awaited cinematic re-telling of Homer’s Odyssey. Matt Damon plays the hero, Odysseus, travelling home to his wife and son after the Trojan War and braving storms, sirens and shipwrecks over the course of a decade-long voyage.
While his adventures are sure to draw the crowds, this region needs no Hollywood embellishment. Among its horseshoe bays, Stygian caverns and cliffside ruins there is a powerful sense of ancient footsteps at every turn, and I’m feeling more than the usual pre-voyage excitement as I board Variety Cruises’ three-masted, 49-guest MS Galileo at Piraeus, just south of Athens, to begin an odyssey of my own.
On one level, my small-ship adventure is a timely voyage to coincide with this summer’s blockbuster. On another, it’s a journey of 2,500 years, back to the birth of Greek civilisation via amphitheatres, fragrant vineyards and sun-baked hilltop tavernas.
And so, with sails cracking in the Aegean breeze, we set out to sea, propelled by the prospect of adventures to come.
Delphi and Olympia by tall ship

Our first stop is Delphi, made famous by the high priestess whose divine prophecies made her the most powerful woman in the classical world. Today, the site’s stone columns and grand theatre stand beautifully preserved on a mountainside, where our wonderful guide and historian, Evgenia, shares tales of this sacred site.
As we slip away, several falcons take flight towards Mount Parnassus, home to Apollo and the muses. This mystical mountainside is still on our minds as we sail towards Olympia, revered as the birthplace of the Olympic Games.
“Today we are going to meet Zeus,” Evgenia announces, with a familiarity towards the gods that feels distinctly Greek. Dotted with temples, the verdant site has changed little in the past two millennia.
Back on board our endearingly small ship, skirting the scenic coast that stars in The Odyssey, we feel truly transported back to ancient Greece. My fellow cruiser Eric, a gendarme from France, is enchanted by the tall-ship experience: “I chose this voyage to travel in the footsteps of the ancient Greeks on a masted ship, closest to how these legendary seafarers once travelled.”

Guests range from history buffs and tall-ship fans to those who simply wish to lap up a cluster of UNESCO World Heritage Sites on a cruise that makes it all so effortless. There are Texan ranchers and English bankers, all drawn by the peacefulness of a shoulder-season cruise and the soothing rhythms of life aboard a traditional masted ship.
Our cosmopolitan party tucks into delicious meals on the main deck, where dinner is preceded by talks on Greek mythology, wine and traditions, and even a spot of Zorba-style dancing.
Buffets of houmous, stuffed vegetables, smoky aubergine salads and kebabs give way to dinners of sea bream and charred fennel, with honeyed millefeuille adding a Gallic twist.
Pleasingly, we learn how to make syrupy, nutty baklava for ourselves, just the way it was done by Granny Kiki, matriarch of the cruise line’s founding family.
Nolan’s Pylos and the Mani

Small-ship cruising is about intimacy, old-world authenticity and calling into tiny bays where only locals usually go. One such haven is Pylos, a safe anchorage featured in the Nolan film but more famous for the Battle of Navarino in 1827, when a British and French-led expedition defeated the Ottomans here, paving the way for Greek independence three years later.
This was the last major naval battle to be fought solely with sailing ships, a point not lost on Nolan, who speaks of seeking locations that are “timeless yet immediate, shot on real waves in real places.”
Just to the south, an even more evocative spot is Methoni Castle, a sea-facing Venetian fortress and Ottoman prison with an offshore octagonal tower.
In the film, we see Odysseus’s son Telemachus – a cloaked Tom Holland – searching for his father but finding him neither here nor at Nestor’s Palace, a prehistoric hilltop site some way to the north. Odysseus encountered a storm at Cape Malea, further east, but our ship sails on safely to Gythio, once used as a naval base by the Spartans.

Here we drop anchor in the secluded bay and find ourselves torn between sunset-gazing, swimming and petting the stray cats who are all too happy to greet us on shore. We settle on visiting Greece’s finest caverns, a glittering stalactite underworld, discovered as recently as 1949.
Gythio is the gateway to the Mani peninsula, the windswept tip of the Peloponnese and home to the Maniots, direct descendants of the ancient Spartans. While Athens birthed democracy, Sparta was a closed, militaristic society, and it shows in the defensive tower-houses that crouch in this menacingly stark landscape.
We drive deep into Maniot country, famed for its barren rocks and blood feuds. Even if the vendettas are mostly consigned to history, our guide Evgenia warns, “Don’t mess with the Mani – you can end up dead.”
Epidaurus, Mycenae and a Nafplio farewell

Thankfully unscathed, we call into Monemvasia, a Gibraltar-like citadel reached across a narrow causeway. As we sit sipping golden Malvasia wine, made here since ancient times, it’s easy to imagine Odysseus’s sails gliding by these sheer sea walls. And given the views of vaulted alleys and Byzantine churches, it would be scarcely more surprising to see crusader knights come clip-clopping down the cobblestones.
Our voyage encompasses yet more UNESCO World Heritage Sites on the way back to Athens. First, we explore Epidaurus, the best-preserved Greek amphitheatre in the ancient world, where the stage is still used for performances, thanks to perfect acoustics.
Dedicated to Asclepius, the god of medicine, the site doubled as an ancient spa resort, blending drama and sport with sacred medicinal rituals using healing herbs.

Next, we clamber up to the Bronze Age citadel of Mycenae, home of mighty King Agamemnon, the Greek commander-in-chief during the Trojan War. Mycenae gave birth to one of the greatest civilisations of Greek prehistory and still astounds with its massive Cyclopean Walls, named after the one-eyed giants of Greek mythology.
Back aboard MS Galileo we begin the leisurely loop back to Piraeus, sailing into Nafplio, once the fledgling capital of modern Greece but now a genteel port with bougainvillea-draped houses and a handful of luxury boutiques.
With its seaside tavernas and picturesque Venetian and Ottoman forts, Nafplio is postcard-perfect, and a fitting farewell to the Peloponnese.
Unlike Odysseus, we have no need for the worry beads and evil-eye amulets that hang in every doorway. Even so, on the advice of every superstitious Greek we meet, we stock up on charms. In a land so steeped in myth, it’s wiser not to provoke the fury of the gods.
Extend your voyage
If you want to bookend your cruise to ancient Greece with hotel stays in modern-day Athens, you’ll be spoiled for choice.
For romance, choose Herodion, a family-run hotel set just below the Acropolis, with a rooftop cocktail bar and beguiling views of the Parthenon bathed in moonlight.
To sample the buzzing nightlife of Plaka district, try sleek La Divina, a boutique hotel where opera diva Maria Callas once sang.
Alternatively, British Airways’ new Gatwick-to-Kalamata route puts the southwestern Peloponnese within easy reach, making the five-star resorts of Navarino Bay a tempting base for your post-cruise adventures.
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