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023 - Chaotic Customs & Greek Serenity: Sailing from Italy's Heel to Greece's Doorstep

  • Writer: Heath Tredell
    Heath Tredell
  • Aug 16
  • 8 min read

Alright, gather 'round, fellow wanderlusters and armchair adventurers. Heath here, reporting live from the gently rocking deck of the good ship Sawasdeekat (which, for the uninitiated, is Thai for a very warm and welcoming "hello," and also the name of our beloved floating home – a St. Francis 48 Catamaran built for eating miles and, more importantly, eating well). My co-captain, the illustrious Pookie (you might know her from that little cooking competition show… MasterChef? Rings a bell?), is below decks, probably conjuring something magical from a tin of beans and a lemon. Priorities, people.

A Portly Heath Goosewing Sailing
A Portly Heath confidently strikes a pose on the deck, showcasing the impressive goosewing sail configuration beneath a clear blue sky.

Our last dispatch saw Pookie cooking in London and us bidding arrivederci to Ragusa’s baroque splendour. We filled Sawasdeekat’s tanks to the brim – water, wine, and enough pasta to appease even the most demanding Italian grandmother spirit – and pointed her nose towards Torrefano. The wind? It was playing hard to get. Lighter than Pookie’s touch on a soufflé. But sailors adapt! We unleashed the sails in a goosewing configuration – picture a majestic albatross stretching its wings wide – and coaxed a respectable 4.2 knots out of the languid Ionian. Respectable, considering the breeze was barely whispering at 5.4. The reward? Water so clear and blue it looked like liquid sapphire poured over the world. And then… puppies. Overexcited, impossibly sleek, grey torpedo-puppies. Or as most sailors call them, Dolphins! They raced our bow wave, slicing through the turquoise, grinning their dolphin grins, performing aquatic acrobatics just for us. It was pure, unadulterated joy, a serotonin injection straight into the soul. They weren't just swimming; they were celebrating the sheer ridiculous brilliance of being alive in that moment. Take that, Monday mornings!

 

A quiet overnight in Torrefano, another in Augusta (think less ancient Roman, more functional port resupply), and then… Deep Breath Time. A 67-mile crossing lay ahead. Not just any crossing, mind you. This was the leap across the Ionian Sea (or at least a generous sip of it), skirting the Spropolo shoals. We were officially tiptoeing along the very toes of Italy’s boot. Our mission? To tickle the coastline all the way east. We made charming pitstops: Soverato, a gentle introduction; Le Castella, guarding its dramatic island fortress like a stone sentinel; Crotone, humming with ancient Greek whispers beneath its modern skin.


After Crotone came Cariati. A blink-and-you-miss-it kind of place on the map, nestled deep in Calabria. We dropped anchor in the dark, breathed in the salty air… and then Pookie’s phone pinged. A message. From a local. "Pookie! Had we known you were here, we would have welcomed you into our home! Shown you the town!"

Record scratch.

Hold the anchovies. Here?

In the very marrow of Italy’s instep? People recognised the MasterChef magic? Pookie beamed, radiating a warmth that could probably cook pasta al dente at ten paces. It was a humbling, hilarious reminder that fame, even culinary fame, has tentacles longer than a well-stretched mozzarella. We were genuinely touched, though sadly, our schedule was a cruel mistress. We couldn’t linger for the grand tour.

 

A Gallop through Gallipoli

Gallipoli in Italy
Gallipoli - No Not THAT one!

Our sights were set on crossing the Gulf of Taranto. Destination? Gallipoli. No, not the Turkish one dripping with Anzac lore. The Italian Gallipoli. The lesser-sung, sun-drenched, Puglian pearl clinging to the Ionian coast. And oh, did it charm the deck shoes off us. Three glorious days vanished like local friselle crumbs. By day, the old town was a labyrinth of honey-stone alleyways, serene and timeless, whispering secrets from fortified walls. Sunlight dappled through laundry strung like festive bunting. By night? The passeggiata exploded. The seafront promenade became a pulsating artery of life – street performers juggling fire, musicians coaxing soulful tunes into the warm air, families strolling, gelato melting faster than resolutions. The aroma! Grilling seafood, sweet pastries, the tang of the sea. Gallipoli possessed a deliciously split personality – contemplative monk by day, exuberant flamenco dancer by night. We feasted. We wandered. We absorbed. We were psyching ourselves up, you see. Gallipoli was the calm before the real storm: an 81-mile crossing to Greece. Our biggest yet. A proper bluewater baptism.

The only fly in Gallipoli’s ointment? The anchorage just outside the harbour. It wasn't just an anchorage; it was a graveyard for forgotten fishing gear. Twice! Twice! Our trusty anchor snagged not on Neptune's trident, but on the ghostly remnants of abandoned lobster pots and snarled fishermen's ropes. Hauling them up felt like wrestling angry, waterlogged ghosts. Each time, we emerged victorious but muttering salty curses under our breath. Note to self: Gallipoli harbour entrance – approach with the caution of a cat burglar in a room full of mousetraps.

 

Offshore across the Ionian Sea:

The Long Day dawned. 4:00 AM. Stars still blazing, coffee blacker than the abyss. We slipped our lines… only to immediately snag another phantom fisherman’s rope. Seriously?! This felt personal. Freed once more (muscles protesting), we endured three solid hours of diesel-powered purgatory. The wind was comatose. Then… a sigh. A whisper. A gentle nudge. The sails, heavy with sleep, finally stirred. Up they went! Course set for Othonoi, a speck on the chart northwest of Corfu. And then… magic. Sawasdeekat woke up. She sliced through the suddenly cooperative Ionian like a hot knife through… well, through Pookie’s perfectly tempered chocolate. The miles unfurled beneath our hull. By 4:30 PM, land ho! Othonoi – Greece’s westernmost outpost, the largest of the remote Diapontian Islands, a rugged, green jewel rising from the deep blue. We’d averaged a very respectable 6.5 knots. Triumph tasted sweeter than baklava. We dropped anchor in a quiet cove, the silence profound, broken only by the lap of water and the sigh of utter relief. Home for the night: Greece. We’d made it!

 

Morning. Sunshine. Optimism... PANIC!

We set sail for Corfu Town, visions of Venetian architecture and spicy sofrito dancing in our heads. Then… The Panic. Mid-channel, a horrifying realisation struck like a rogue wave. The Corfu Tourist Tax! We hadn’t applied! We hadn’t paid! Visions of stern Greek Harbour Police officers, eyeing us like suspicious squid, filled my mind. Arrest? Fines? Confiscation of Pookie’s emergency olive oil stash? Unthinkable! Reasoning (panic-driven) prevailed: Exit Greek waters immediately. Apply online. Pay. Re-enter legally. Simple! Genius, Heath. Pure genius.

 

We altered course. Albania beckoned. Rugged coastline, unknown quantities… and then… The Dread. A frantic internet search revealed Albania, too, demanded 48 hours notice for arrivals! We were adrift in a bureaucratic no-man’s-land! Trapped between the Albanian Rock and the Greek Hard Place! We stared at each other. Sawasdeekat bobbed patiently. This wasn’t an adventure; it was a Fawlty Towers episode directed by Kafka.

 

Decision: Full reverse. Face the Greek music. Maybe they liked MasterChef winners? I attacked the Greek tax portal like a man possessed. The website? It possessed the functionality of a chocolate teapot. Error messages bloomed like digital weeds. "NO." "ERROR." "TRY AGAIN LATER (MUCH LATER)." It was a petulant child refusing to eat its digital greens. Utterly, infuriatingly useless. Exhausted, fed up, feeling like our passports were about as useful as a soggy gyro wrapper, we slunk into Kassiopi, a charming harbour on Corfu’s north coast. Anchoring was a fiasco – the port side bay offered zero holding (like trying to grip wet soap). Starboard side, finally, the anchor bit. We slumped. Defeated. Waiting for the knock.

 

Midnight. The quiet harbour hum. Then… the low thrum of an engine. A police boat. It motored slowly, deliberately, past Sawasdeekat. A spotlight casually swept our deck. My heart hammered a tarantella against my ribs. This is it. The brig. Bread and water. But… the light moved on. The boat continued its patrol. They hadn't stopped! Hope, fragile and fluttering, reappeared.

 

Next morning, nerves frayed like old rope, we motored into Corfu Town harbour. Deep breath. Time for Customs, Immigration, and the Port Police – the unholy trinity of entry. I launched into my prepared speech, waving my phone like a white flag: "We tried! Honest! Your system… it’s broken! Like a… a… chocolate teapot!" (The analogy seemed internationally apt). I poured on the charm, thick as tzatziki. Pookie, ever the diplomat, chimed in with her megawatt smile: “We come in peace! And also… profound hunger. Where, pray tell, does one find the finest moussaka in this fair town?” Her MasterChef aura shimmered palpably.

The officials exchanged glances. Shuffled papers. There were forms. So many forms. Bless two incredibly patient female customs officers who basically filled them for us (my Greek extends to ‘yassas’ and ‘efharisto’ – useful, but not for bureaucracy). The lead officer, face like a weathered cliff, finally spoke:

*   “Name?”

*   “Nationality?”

*   “Purpose of visit? Tourism? Pleasure?”

*   Pause. A raised eyebrow. “Are you sure you are not… pirates?”

(Mental Note: If we were pirates, we’d definitely have better paperwork. And probably eye patches. And a parrot. We had a catamaran named ‘Hello’ and a TV chef. Not exactly Blackbeard material.)

 

Pookie’s moussaka inquiry hung hopefully in the air. Then… the miracle. A shrug. A resigned sigh. “The system… po po po… it is broken,” one muttered, stamping our papers with a satisfying thwack. “Just… pay the tax now. Cash. And don’t… tell Athens, okay?” Relief flooded through me, warm and dizzying. Jail averted! We were stamped, legal, and only slightly convinced we were now on an EU watchlist titled ‘Hopeless Sailors Who Can’t Follow Directions (But Like Moussaka)’. Cash handed over, we practically skipped (as much as one can skip on a boat) to anchor outside Mandraki Marina. Freedom!

Mandraki Marina at night
Mandraki Marina Looking Magnificent

Christening Corfu

The rest was a blissful coastal amble. Benitses for a night. Then Lakka, Paxos.

Picture this: A near-perfect circular harbour, crammed tighter than sardines in July. Boats packed bow-to-stern. The only solution? Shore lines! Like a proper old salt (or a complete newbie pretending very hard), I swam ashore, rope clenched in teeth, and secured Sawasdeekat to sturdy rocks, preventing her from swinging into our neighbours. Pride? Immense.

Then came the charter flotilla. Four boats, crewed by people who clearly did this weekly, slid into an impossibly (to me at least) small gap beside us with nonchalant precision. (I think if I leaned out my bathroom window I could have grabbed their shower gel!! So, suddenly, our personal space shrank to ‘could-pass-the-toothpaste’ levels. It was hilarious, chaotic, and utterly Mediterranean. Ashore, Lakka twinkled – a postcard come to life. We dined, our dinghy parked casually on the beach just metres from our table. Perfection. Next, Gaios, Paxos’s main port.

We anchored south of the entrance, dinghied in, explored, ate, and did the whole touristy thing of looking round whilst trying to nonchalantly look like we've seen it all before. Bliss. But… the Meltemi wind decided to RSVP to our little anchorage. Returning, Sawasdeekat was rocking like Bill Haley himself was on deck. It was untenable and all other boats had already left this crazy bit of bliss. We waited for a lull, fired up the engine, and motored around the corner, finding a blessed shelter from the blow next to some local goats. Keen to see more of Paxos, we nosed down the south coast. And found paradise. A tiny, hidden (UNNAMED) cove, just for us. Turquoise water, sheer cliffs, utter peace. We tied off securely (rock avoidance paramount) and named it on the spot: Lesianitis Cove, after the little village perched precariously above. We even logged it on Navily – our small contribution to the sailor’s map of delights. We believe you can now find Lesiantis Cove on Navily! The View? Stunning, Serene and totally alone.

However, time was ticking! Pookie’s sister was inbound! We dashed to Sivota on the mainland for a sunset meal. The sunset blazed, painting the sky in fiery oranges and purples.

Sawasdeekat at Night

The food was sublime. The wine flowed. And then… the minor snag. In the post-sunset, pre-moonlight gloom… we forgot where we parked the boat. Seriously. Drifting in the dinghy, peering at shadowy hulls, trying to remember if Sawasdeekat had the black bimini or the slightly faded one… minor panic! We found her, of course (she’s rather hard to miss, being the only small apartment block with sails and a black stripe down the side), and navigated back under the emerging stars, laughing at our own forgetfulness.


So here we are, back near Corfu Town. The adventure continues! Next time? Pookie’s sister arrives! Expect kayaking chaos, drone footage that hopefully avoids other boats/seagulls/important landmarks, and explorations of Corfu Town’s labyrinthine alleys and fortresses. Will we master the bus system? Will the drone end up in a pastitsada? Stay tuned!

 

Until then, fair winds and calm bureaucracies (ha!),

Heath (& Pookie, probably foraging for wild oregano as we speak)

Aboard S/Y Sawasdeekat

Somewhere delightfully Greek

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