An Aegean Odyssey: Sailing The Greek Islands

An Aegean Odyssey: Sailing The Greek Islands


“What are the children of men, but as leaves that drop at the wind's breath?” It's the last message I read as I slam shut my dog-eared copy of The Odyssey – compulsory reading when you're whizzing across the blue-green waters of the Aegean Sea. The wind, the same warming, revitalizing Greek wind that Homer himself would have felt as he roamed the cliffs of Turkish Anatolia, streams through my hair now, and catches the sail. It billows and we're off. I, like the fabled leaves of Homer's image, am blowing in the salty gales that have taken so many across this beautiful corner of the Med.

There's really nothing quite like it: Leaving behind one glimmering bay of alabaster-white pebbles and sun-reflecting shores in the morning, arriving at another – just as handsome, just as beguiling – by night. Time in between has largely been spent soaking it all up. "Breathtaking" might be a cliché, but the peppering of islands that is the Cyclades and Dodecanese really is a gasp-inducer, a "breath-taker-awayer", if there ever was one.

I drop my tome and gaze out across the timber deck of the yacht. Plumes of salt spray fizz upwards from the hull as it surges over the light swells. In the distance, I can see a whitewashed town cascading down the rugged ridges of one island. I'm told it's Nisyros. I'm told it peeks out of the Mediterranean Sea in the shape of a hulking volcano because, well…. because it is a volcano.

You could say I've been de-sensitized to those sorts of awesome factoids about the Greek Islands. I've just left Kos, you see: Kos, where it's common local knowledge that the island was once trodden by ancient giants; Kos, where the rugged rocks of Gourniatis Cape are said to have shipwrecked even the mighty Hercules himself. I've taken it all with a pinch of salt. And a platter of tangy katimeria cheese from the grill. And a swill of Greek wine between the thumping bars of Nafklirou Street (talk about legends, the parties there are downright legendary – sorry, couldn’t resist).

I turn to give Kos a final glimpse. I see its ochre-brown coastline fading into the heat haze in the distance. I see little wisps of whitewash peppered with points of bright magenta – its cubist towns and their strings of bougainvillea – go back into hiding between the rocky headlands. I see its bobbing boats and ridges of fig orchards dwindle in the evening light. I see it dissolve behind the wash of our yacht's wake like something out of a Homeric myth.


Kos to Astypalaia, or, mainstream to off-the-beaten-track

There are few tourist ferries that make the journey from Kos to little Astypalaia direct. It's not far. It's just that the island is content outside of the limelight. You won't really see it in the travel brochures for the Aegean, and you'll rarely catch your vacationer mates slinging it up there in their holiday Facebook statuses. "X checked into Astypalaia", said no one, ever.

I thought I'd break the mold and make this one a stop off on my Aegean odyssey. Okay, my tour organizers told me to. Those long and poetic odes to Astypalaia's rare beauty were just too hard to ignore. They spun tales of cubist harbor towns where the fish tavernas still tap with the energy of Zorba – everyone's favorite Greek. They told of flower-strewn streets and bobbing boats and only locals. They talked – in hushed whispers lest anyone else should hear – of Agios Konstantinos Beach, where an arc of dull-toned pebbles slope down to a sea so clear and blue you'd think it had been photoshopped. Sold. Ticket for one please.

As the yacht drifts into anchor, I can see that Astypalaia isn't going to disappoint. The sun is already setting over the main town. It's a blanket of brilliant white houses tinted cinnamon in the twilight. The silhouette of Astypalaia Castle looms high above it all, marking the heart of the settlement that itself drapes down the dusty ridges above a sloshing, sky-blue sea.

In a heartbeat, I'm up there. I'm wandering the narrow lanes and smelling sizzling whitefish doused in lemon juice, twisting and turning between the stone walls of the houses. I'm passing tanned locals who chatter in the evening winds that filter through the medieval lanes. I'm sipping a cold beer as I look out across the bay. The bald coastline of this untrodden island is like the Greece I imagine from Homer. It's empty; empty save for the village life that pulses in the shadow of its muscular Venetian castle.

Screen Shot 2017-09-22 at 11.43.20 AM.png

Astypalaia to Santorini, or, unspoken wilds to volcanos

As you pass across the cobalt waters that divide the Dodecanese in the east and the Cyclades in the west, you pass some mythic places. The most iconic of the lot is the pinpoint island of Anafi, which is said to have been miraculously revealed to the Argonauts by Apollo himself. It lurches above the Mediterranean with pockmarked cliffs that look like the petrified faces of ancient demigods. Here and there, small taverna towns hide in the creeks and gullies. It feels like somewhere so far away but yet I'm close enough to swim there. The waves keep sloshing. The yacht bounces on.

Then I see it: Santorini. Few islands in the world have such a commanding stature. Its eastern haunch is the first to be sighted from our decks. I feel like a pirate glimpsing a long-lost and cursed treasure island as I gawp, wide-eyed across at its scabrous cliffs and mountaintops. Next, we drift around the coastline and the astonishing collapsed caldera of Santorini comes into view. It's beautiful and terrifying at the same time; a reminder of the metamorphic force of volcanic eruptions, and a poster boy for the spectacle that is the Greek Aegean.

Later, I'm looking down on the caldera from a perch in the town of Fira – the capital. It's a seriously romantic spot, especially as the sun dips low to the horizon and the speckling of rocky promontories in the distance are illuminated in some ethereal mix of sea blue and evening ochre. I try to imagine what the ancient Minoans would have thought of the sight. They were here, nearly 4,000 years ago, one of the most successful civilizations in Greece, brought low when the mighty volcano of the isle exploded in plumes of ash and magma in the middle of the Bronze Age.


Santorini to Ios, or, panoramas to party nights

I leave Santorini still wowed by its profile. Like Kos, I see it dither into the heatwaves as the yacht sails northwards. It's soon gone, a lost ancient volcano in the middle of the Med. I turn my sights to the bow, its thud on the waves heralds where we're off to next: Ios.

This thumping party isle is the one to let your hair down on. The one to glug ouzo on. The one to trade in myths for mythic hangovers and to spend all day sizzling them off on the beaches. I'm looking forward to seeing another side of the Aegean – its apparently more raucous side.

Later and Ios isn't disappointing. I'm doused in beer and water in a pool party. Rocky coastal mountains peppered with brilliant white villas loom on one side; the glistening Aegean Sea unfolds on the other. I'm not sure if I can make out my own yacht bobbing between the forest of sails that crowds the harbor. A minute later I don't care if I can or not – the bubbly's out and the toasts are flowing.

The night continues on amid the narrow lanes and squares of little Chora town. It's a beautiful place to get wild. Between Long Island Iced Teas – bargain Long Island Iced Teas might I add – I can gawp upwards and see the outlines of glowing Venetian windmills on the hills. Or, I can make out the Greek blue domes of an Orthodox church, the honey-hued glow of the moon casting an eerie light across its frontispiece.

The next morning and I'm lucky enough to have hit the travel hangover (a unique phenomenon of mine that means hot weather staves off the bad feeling. Anyone else?). I'm perky and fresh. I spend some hours hopping between the more off-beat beaches of little Ios. I discover that this speck in the Aegean isn't just for pool blowouts and nighttime shindigs. It's also got glowing Mylopotas Beach, where Tiki sun umbrellas cast shade over a pearly shoreline. It's got Koumbara, the taverna-topped cove. It's got hidden Papa bay, where the waters seem to take on a Caribbean-esque tone.


Ios to Paros, or, from hedonism to old Greek life

Hupate (hangover-update): It's finally set in – a day late. Or, maybe it was that flurry of chart-topping beaches that made me reel. Either way, there's no better cure than Paros, surely? I've been told it's a place away from the crowds, where lazy Greek life unfolds in the hilltop villages and the bays sparkle in yellow beneath the sun. That's what I've been told. I'm looking forward to it.

Sails reigned in and anchors aweigh, I'm strolling along the quaysides of Naousa. At first, I'm struck by just how many people there are – I was told this was a quieter place to nurse a delayed ouzo-induced haze. Then I get away from the docks and I realise that those folks are just ferry hoppers, hitting Paros for a meager hour or so before they head off again on a connecting boat to wherever it is in the Cyclades they've settled on.

I'm glad as I nestle myself in a comfy wooden chair in a local taverna beneath the blue-hued domes of the Church Agios Nikolaos. There's just the footsteps of a few other people pattering around me as I order my cocktail (hair of the dog and all that), and the creak of the rigging that echoes from the jetties and the boats. I sip and sleep (I think), and before long I'm back to my headache-less self.

It leaves some time to see Paros the island. I hitch a ride to Lageri Beach – the grill house griller back in town recommended it. It's majestic and pretty. It shimmers an ivory-white color and has hardly anyone else sunbathing along its shores. The water follows the contours of the glowing sands as they wiggle around the Parian coast. It's such an enticing blue that I'm in there in no time, reclining on my back and feeling the swill of the warm currents as they pass around my body.


Leaving Paros

Leaving Paros isn't easy. It feels like I'm being sucked out of a travel brochure I've been lost in for days. Perhaps that's because I know it's the big city of Athens that awaits me next time I dock. Perhaps it's because all the memories of my Odyssey through the Aegean – from the fading harbors of Kos to the chattering locals of Astypalaia, through the jaw-dropping vistas of Santorini and betwixt the un-remember-able nocturnal bars of Ios – come flooding back to me now.

They flood back and the Aegean swills around the hull of my yacht, sealing me off from the jetties of little Paros as I sail away, the land vanishing, nostalgically, over the horizon; the wind blowing in a warm breeze across the deck.


These snapshots of life in the Aegean Sea are just a taster of some of the amazing destinations we visit as part of our LBW YachtLife. You can go and explore the sparkling coves and shimmering beaches, the whitewashed towns and lively tavernas yourself if you want – just check out our departure times for upcoming trips through the isles of Greece. See you on board!

Join our Newsletter to be entered to win a $500 voucher each month, along with updates on new adventures, contests and promotions!
10 Reasons To Pack Your Bag

10 Reasons To Pack Your Bag

14 Things You Definitely Need In Your Backpack While Abroad

14 Things You Definitely Need In Your Backpack While Abroad