The pages of this summer bumper edition typically carry the death-defying Aussie larrikin exploits of my brother, but what happens if you take him abroad? It would be a mistake to believe a strict itinerary could contain his barely survivable – legally dubious – chaos.

And so it was that we found ourselves in convoy around the Italian countryside, crammed into a pair of cars that resembled colourful bugs with battered side mirrors. Their satnavs refused to turn off ‘tourist mode’ and so I was given a paper map and promptly invented a new system of directions that included an Italian left (which meant the ‘middle of three lefts’) and the rapid screech of ‘left left left!!!’ (which meant the hairpin option). We discovered the ‘ring road of doom’ around Rome where the signs were placed after the turnoff to inform you of which exit had been missed, and then enjoyed the saucer-sized mirrors scattered along the Ligurian coast which ensured a clear view of the tourist bus that was about to run you off the cliff and into the Mediterranean.

My brother is half-Italian, and seeing him in his natural habitat explained a lot of his survival oddities. We passed rural Italians resurrecting old cars underneath the bowers of lemon trees which scrambled up the rocky coast. They tinkered long past insanity – spending a fortune to save a cent – but their busy hands make light work of the world and their afternoon wine is well-earned. We admired them, along with the sunset view over a land that buried its civilisations without any particular sympathy.

I make an excellent satnav, and our car arrived on time at the Saracen fort overlooking the sea. The hotel is wrapped around the fort with bits of the past jutting out from its crumbling veneer of modernity. While looking for the pool, the elevator delivered us to an abandoned, rock-walled corridor. Pitch black, it eventually opened directly to the sea, as if it were the tunnel at the end of life. On both sides were suits of armour, facing each other in pairs with only their sharp metal edges visible. Cannons were fired at dusk, shuffling free gravel from the cliffs above. ‘Back-burning for cliffs’ we called it. Having reached the pool, we hid as rocks plopped into the water.

My brother and his son arrived very late, nursing tall gin and tonics as the light faded over the Amalfi coast. ‘What happened to you?’, he was asked. ‘Naples….’ A poor choice on the freeway flyover had sent them into the sprawl of Naples’ docklands. ‘Lost, we pulled up to this servo for a map. Overgrown – full of weeds. This massive black guy came over. A drug dealer. We tore straight out of there and narrowly missed a car belting through an intersection followed by the Polizia. These were sub-villages of crime. Cobblestone driveways. Gated mansions – one had a jet black, unreleased Mustang out front. Our Mercedes-Benz was screaming, ‘TOURIST!’ in self-defence. We were like pigeons in a f—ing lion exhibit at the zoo surviving thanks to the bewilderment of the lions.’ Naples didn’t bother to camouflage its criminality and he’d never been so happy to see a group of prostitutes writhing by the side of the freeway with Vesuvius smeared as a shadow on the horizon. The old goat track that wandered into Amalfi, feared by tourists, came as a relief.

We had our own mishaps in hilltop Etruscan villages that acted as reverse ant-traps where the elderly would bring out chairs to watch tourists panic-drive down stone stairways. Eventually, we attempted a day trip from Perugia to Florence. We arrived at the Uffizi Gallery and joined the mob trying to photograph Michelangelo’s ‘David’ while being hissed at by security. My friend kept her camera at waist height and angled it up, taking hundreds of sneaky shots. Shots, we later discovered, exclusively of David’s tackle.

‘We were so drunk,’ my brother explained, after they failed to arrive. They’d missed a key turnoff on the way to Florence. ‘Fifty metres down from the Brufani Hotel there was a bus layover – a ‘roundabout-esque’ area with a stone gutter. I took that – shredded the front and back tyres – and limped to a carpark at the bottom of a mountain. Searching for tyres, we walked past a high-performance dragway company, which seemed ridiculously over the top, and found a mum ‘n dad business.’

The bloke didn’t speak English but the wife eventually decoded our panicked hand signals. ‘She burst out laughing, spoke a thousand-miles-an-hour to the husband, and then took us straight to the Mafia-owned dragway. Standard tourist rate for a tyre is 350 euros. There we were next to the race cars. The owner, a 65-year-old, six-foot, cigar-smoking man in the background. He said nothing as our car was dragged into the backroom. Four hours. 700 euros in cash. After that, we went to the pub. F–k Florence.’

Our story ends in Hvar, Croatia, where we abandoned the roads and hired a gulet with a captain who shared his home-brew something on the final night. Hvar is one of those ports where everybody gets into trouble, even before they reach the bars. We watched as a group of tourists, three sheets to the wind, fell from their boat into the waiting Zodiac having failed to operate the ladder. They returned in worse shape, and realised the polished sides of a sailing boat make it difficult to board. They spent hours trying to climb a stray anchor rope while we turned up the music and cheered them on whenever one fell into the Adriatic.

After ten or so shots of the captain’s green stuff, my brother stripped naked and took a running leap off our gulet and started paddling around the boat like an excited puppy. He had placed a lot of trust in his sister and son that we would lower the ladder… I couldn’t find a way to get off the deck, so I raised my glass in a toast. My nephew turned the music up even louder. The guys scattered in the water around the next boat started singing.

In the morning, the cook laid out a breakfast of whole octopus with its tentacles curled elegantly down the table. My brother’s eyes widened. Apparently, the tentacles were moving on their own.