The green-fuzzed outcrop was tantalisingly close. I could swim to it, couldn’t I? Surely, in just a few strokes across the narrow blue channel, I’d reach its shores? I could be, briefly, queen of my own private isle... But then Rob found a nice spot for lunch, and the picnic’s deliciousness trumped my desire to splash over to uninhabited Partridge Island. (Uninhabited, that is, aside from a colony of little penguins).

Tasmania is a rugged little heart shape loitering 150 miles south of mainland Australia. It’s the country’s island state – but has a further 300-odd isles sprinkled off its shores, many of which are surrounded by even smaller outlying atolls. It’s like the geological equivalent of Russian dolls, a chain of ever decreasing nuggets, and each adds something to the Tasmanian story.

“Bruny Island is like Tasmania in a microcosm,” explained my guide Rob Knight, as we gazed at Partridge from one of Bruny’s empty, white-sand beaches. “It has virtually all Tasmania’s microclimates, most of its wildlife, rich explorer and Aboriginal history, amazing food.”

Neck Beach, which connects the north and south of Bruny (Andrew Wilson/Tourism Tasmania)

Bruny is also easily accessible from Tasmania’s capital, Hobart, where Rob begins his award-winning Bruny Island Long Weekend, a two-night trip to the island, featuring boat rides, coastal hikes, a private wilderness camp and exquisite Tassie produce. Only around 10 per cent of visitors to Tasmania go to Bruny, most just for the day. Rob reckons it’s worth lingering. “Bruny attracts creative, inventive types,” he said. “Artisan cheese makers. The southernmost vineyard in Australia. A recent exhibition in Hobart featured 60 Bruny artists – not bad for an island of just 600 people.”

Rugged, 31-miles-long Bruny (two islands, joined by a narrow isthmus) is named after Antoine Bruni d’Entrecasteaux, a French naval officer who stopped here in 1792, following in the wake of Abel Tasman, James Cook and William Bligh. D’Entrecasteaux experienced positive interactions with the Aboriginal inhabitants, who’d lived on the island for thousands of years. However, within decades this changed: by the 1830s, most of Tasmania’s indigenous people had either been killed or relocated to far-north Flinders Island for their “protection”.

My history lesson was drip-fed over the weekend, during which we walked through coastal forests, cruised beneath some of the world’s highest dolerite sea cliffs, spotted wallabies, quolls and other antipodean wildlife, and learnt to shuck oysters fresh from the sea.

Accommodation was at Rob’s safari-style camp, where I listened to tales of Tasmania on the decking, serenaded by grey shrikethrushes and the breeze rippling through the towering gums, and enjoyed delicious meals of pulled pork from a rare-breed Bruny smallholding, wallaby seared with native pepper, delicate Huon salmon, and panna cotta drizzled with leatherwood honey.

The one strand of Tasmanian history that Bruny lacks is convict heritage – though the island’s lighthouse, one of the oldest in Australia, was built by convict hands. To get a better understanding of this, I headed north up the east coast to Maria Island.

Despite the relatively small size of Van Diemen’s Land (as Tasmania was known until 1856), the state received 72,000 criminals – 42 per cent of the total number transported to Australia. Most were not locked up on arrival: the whole of Tasmania, an alien land far from home, was a prison. However, penal settlements were created for those who committed offences in the colony. Maria Island was one of these.

Churning in the ferry from Triabunna harbour to Maria, a 30-minute ride, it seemed unlikely that anyone could have escaped it. But escape they did, which is why the first gaol on Maria was short-lived, operational from just 1825 to 1832. Subsequently, a probation station was established, from 1842 to 1850. The remains can still be seen; the old penitentiary is now a hostel, the only option (besides camping) for those keen to stay the night.

Maria Island’s Mess Hall used to house 400 convicts (Peter/Flickr)

My first stop on Maria was the cavernous Mess Hall, which once served 400 hungry convicts; now visitors use it to cower from the rain. Fortunately, the weather soon brightened, so I ventured out – and almost tripped over a wombat, grazing amid the cells. It wasn’t a huge surprise. While Maria used to be a place to rehabilitate humans, it’s now doing the same for wildlife. Since the 1960s the island has been a sanctuary for threatened species.

As I hiked away from the penal ghost town, bound for the twin peaks of Bishop and Clerk, I passed pademelons and Bennett’s wallabies nibbling the heath, Cape Barren geese and Forester kangaroos. I didn’t spy any Tasmanian devils (they’re nocturnal), though 15 were released here in 2012, part of a captive breeding programme to try to save this endemic species, which is being decimated by a facial tumour disease.

Maria Island is one of the best places to observe wombats in Australia

As I followed the trail into the forest of stringybark gums, a pair of kookaburras set to laughing, as if amused by someone climbing a mountain in this gloomy weather. They were right, I saw nothing but cloud from the clifftops, though I knew that to the north lay the fine finger of the Freycinet Peninsula and Schouten Island – my final port of call.

Designated in 1916, Freycinet is (along with Mount Field) Tasmania’s oldest national park. It’s also a candidate for Tasmania’s most glorious – a tendril of land backboned by pink granite hills and edged by blindingly white curves of sand, not least much-photographed Wineglass Bay.

The white curves of Wineglass Bay (Tourism Australia)

A few days later, under brilliant blue skies, I walked to Wineglass; I took a dip in the rough waves and walked to the lagoon just inland, noisy with banjo frogs. There weren’t hundreds of people but, still, it was busy by Tasmanian standards. So to see Freycinet without the “crowds”, and tick off my final island-off-an-island, I boarded the beautiful yacht Volant. With owners Graeme and Kathryn at the helm, we cast off from Coles Bay, Freycinet’s main settlement, named after a Hampshire convict who set up a lime kiln here in the 1850s. Sails billowing, we silently traced the peninsula’s west coast, looking up to the Hazards mountain range and scanning the waves for dolphins.

“On some trips the boat is surrounded by them,” Graeme told me as Kathryn passed over a glass of Tasmanian fizz. “We see whales too.”

Schouten Island

Alas, not today, though I continued to keep an eye out as we neared Schouten Island, which sits off the peninsula. Schouten, a large clump of hilly granite and dolerite, was named by Abel Tasman in 1642. More latterly sealers and coal miners exploited the island’s resources. But now it sits quietly, uninhabited and unreachable without your own boat. It’s another ruggedly handsome outcrop that’s been returned to the wild; it now belongs to the penguins, shearwaters, fur seals and skinks.

With more time, we would have moored off the island, jumped into the waves and swum to Schouten’s sandy bay. But the wind had been too gentle, our progress too slow. “More fizz?” asked Kathryn, as the Volant changed tack and turned for home. Oh well, another island untrampled. “Yes, don’t mind if I do.”

Travel essentials

Getting there

Etihad (etihad.com) and its partner Virgin Australia fly from Heathrow to Hobart via Abu Dhabi and Melbourne.

Tasmanian Odyssey (tasmanianodyssey.com) arranges tailor-made trips to Tasmania. A seven-night self-drive holiday costs from £695pp including car hire and B&B accommodation.

Staying there

The Bruny Island Long Weekend (brunyislandlongweekend.com.au) costs AU$1,695pp (£1015) all inclusive, except flights.

Sheoaks B&B, Freycinet (sheoaks.com) offers doubles from A$200.

Visiting there

Sail Freycinet (sailfreycinet.com.au) runs trips around Coles Bay from AU$320 for two people.