Hobart To Launceston

Described by owner David Walsh – a maths genius/gambling impresario turned multi-millionaire – as a 'subversive adult Disneyland', MONA is unlike any museum you've ever seen. Even the location is astounding with the incredible installation concealed across three levels like the secret underground lair of a Bond villain. An unbelievable collection of super-rare antiquities from the ancient world is displayed beside challenging and often confronting modern art, and there's a whimsical and playful interactivity throughout that encourages involvement from visitors. MONA's the kind of once-in-a-lifetime experience that many travellers visit Hobart solely to see, and it makes a disquieting, disruptive but totally essential bookend to your Tasmanian road trip.

The compact bays and coves of the coastal landscapes around nearby Port Arthur are equally glorious, but such spectacular scenery masks the sombre legacy of one of Australia's most tragic historical periods. Between 1830 and 1877, almost 13,000 convicts were incarcerated here, many for relatively minor crimes, and the Gothic sandstone buildings exude a darkness and despair borne of isolation and imprisonment in such a beautiful location. Because of the remoteness, escape was virtually impossible, and the improbably narrow isthmus north at Eaglehawk Neck was actually protected by the infamous 'Dogline', a terrifying row of big dogs with even bigger teeth. Port Arthur is a destination that demands remembrance and reflection, so try not to rush, and definitely join a historical tour to get the most out of a visit.

More Aussie wildlife awaits at Maria Island, a convict era probation station which is 40-minutes by ferry from sleepy Triabunna. Fuelled by Tasmanian food and wine, the guided three-day/four-night Maria Island Walk is popular from October to April, but for daytrippers the best option is to catch a ferry with Encounter Maria Island and rent a mountain bike to go exploring. Look forward to encountering statuesque Cape Barren geese and grazing wombats and wallabies. For the island's best photographs, ride to the Painted Cliffs, a spectacular area of wave-eroded sandstone with the surreal vibe of a Salvador Dali painting. The sandstones are from the Triassic period, when the first dinosaurs appeared on earth. Low tide is the best time to visit.

After checking out the vineyards and cellar doors around historic Swansea, make the call to stay in the town's excellent heritage bed and breakfast accommodation, or move on a further 52km around Great Oyster Bay to Cole's Bay at the northern end of the Freycinet Peninsula. In an Australian state often adorned with verdant farmland and forest, the bold and stark Mediterranean-looking landscapes are surprising. The best way to explore them is in a sea kayak, and morning kayak tours with Freycinet Adventures usually offer more subdued sea breezes.

When a beach is renowned as one of the top 10 beaches in the world, it's good to have viewing options. Shaped like a perfectly-formed chalice, Wineglass Bay is best seen from above – count on a steepish 90-minute return walk to the best view at Wineglass Bay Lookout. Or stroll along the bay's pristine and sandy arc, which will take you a further 30 minutes steep descent from the lookout down to the beach.

The other option is to view the bay from the ocean on an easygoing four-hour excursion with Wineglass Bay Cruises. Of course, local wines, seafood and cheeses are served when the boat is anchored smoothly off the bay – you're in one of Australia's gourmet hotspots after all – and there's every chance you'll see dolphins, seals and soaring sea eagles.

Just north of town is the turn-off to Douglas Apsley National Park, with excellent bushwalks that take from ten minutes to seven hours taking in river gorges, waterfalls and swimming holes.

After Bicheno, Tasmania's A3 highway continues to hug the state's spectacular east coast to another beach of equal international renown. Head through the laidback fishing town of St Helens, and stop 11km north at Binalong Bay, the gateway to the Bay of Fires. On summer weekends keep an eye out for the funky Pie-O-matic SupernoVan – their Mac & Cheese Royale pie with truffle cheese sauce is a thing of beauty - before strolling along the stunning beach punctuated with spectacular granite rocks tinged with the orange hue of lichen.

Wines from Western Australia's Margaret River region or Victoria's Yarra Valley are justifiably renowned internationally, but for savvy travelling wine buffs, Tasmania is an under the radar surprise. Cool climate varietals enhanced by subtle maritime breezes off Bass Strait include excellent pinot noir and pinot grigio, and Pipers Brook Vineyard's Kreglinger sparkling wines are bottle-fermented in authentic Methode Champenoise style. This is definitely what to crack open if you get a really good score at Barnbougle Dunes.