The ferry from Melbourne to Devonport doesn’t glide across the Bass Strait, it growls and it staggers. Winter swells batter the ship like it’s in a washing machine set to violent spin. Snack bars sway, passengers grip railings, chairs fly and stoic Tasmanians carry on as if it were a bus commute. I alternated between laughing at the absurdity and questioning my life choices. I cursed Poseidon. I cried. The Bass Strait is some of the roughest ocean in the world, where the very cold Southern Ocean meets the nearly as cold Tasman Sea and attempts to make a slurry of any vessel trying to cross.
By dawn, as Devonport’s port lights blinked awake, the horizon calmed and Tasmania stretched into view. The island likes to shake you up a bit before letting you in.
From Devonport I rolled southwest, my destination St. Helens for a respite to “acclimate” after the ride in.
The next day, I am in the car (right hand drive, of course) humming toward vineyards that punch above their weight. Tasmanian wine has gone from underdog to super-duper, its pinot noir and sparkling wines now stacking up against California’s (and Europe’s) finest. House of Arras pours bubbles so precise they make all your pain Champagne, while Pressing Matters’ Riesling cuts through winters sharp beauty.
Between tastings, villages charmed in their own eccentric ways. Richmond preened with its convict built stone bridge (Australia’s oldest), Oatlands was all Georgian austerity and a local pub full of pool sharks. These places aren’t frozen in time—they’re alive, very offbeat, and comfortable with their quirks.
Hobart welcomed me with the swagger of a port town that has seen it all - convicts, whalers, traders, and gamblers wash through. At Battery Point, the Shipwrights Arms Tavern presented me with history, low ceilings, creaky beams, and locals clinking glasses like the pub had been waiting for me all day. Scallop pies are the specialty: buttery pastry, curried filling, the kind of dish you swear is “provincial” until you’ve inhaled two and now you know it’s genius.
Then there’s MONA, the Museum of Old and New Art. David Walsh, a locally grown professional gambler turned professional provocateur, built it into the cliffs of the Derwent River, as if a Bond villain lair and Tony Stark’s mansion made a baby. MONA kidnaps your attention. Sidney Nolan’s Snake coils across an entire gallery wall, while Greg Taylor’s infamous Cunts… and other conversations presents 151 porcelain vulvas in detail. The art is not polite. One of my forever favorite installations is there, 20:50, by Richard Wilson (I saw it at the Saatchi in London many years ago). One at a time, single file and do not touch!
I was so very lucky to retreat to Walsh’s bushland property nearby where the art and architecture follows you along the coastline, into the wild. MONA lingered long after I’d left.
Further south, Tasmania dared me to hike out to Shipstern Bluff (actually, it was my sons who made this request, photos from Shippies). The trek is windswept, cliffs plunging into the sea until the trail drops you above one of the world’s most notorious surf breaks. Waves rise like walls, folding in on themselves with slabs so violent they’ve made legends of those who ride them. I wasn’t among them, but I stayed nearby, sleeping to the sound of the same ocean that spends daylight hours trying to unhinge the brave.
Tasmania kept shape-shifting. At Eaglehawk Neck the land narrows to a thread, once patrolled by dogs to stop convict escapes. The Tessellated Pavement spread out like an ancient mosaic, nature showing off its sacred geometry.
Launceston was the exhale. A long walk along the Tamar River slowed the pulse, willows trailing into the current.
By the time I looped back to Hobart, I’d lost track of the kilometers and the costume changes. Tasmania isn’t an island you circumnavigate, it’s a trickster, truly, an entire continent disguised as a postage stamp. Winter strips away whatever gloss it might tape on for Christmas hols.
I flew home - and I don’t challenge anyone to make the crossing by boat.
Tasmania commanded me to keep up. I’ll make sure you keep up too. Through Robinson & Roam, I craft one of a kind itineraries, mentor you into confident solo voyages, and add the kind of polish that makes every experience unforgettable.
