Sydney, capital of New South Wales and one of Australia’s largest cities, is best known for its harbourfront Sydney Opera House, with a distinctive sail-like design. Massive Darling Harbour and the smaller Circular Quay port are hubs of waterside life, with the arched Harbour Bridge and esteemed Royal Botanic Garden nearby.

Hobart is Australia’s second oldest city and state capital of Tasmania. Home to more than 90 National Trust buildings, Hobart combines colonial character with a metropolitan lifestyle. It is the gateway to Tasmania’s other scenic attractions and a range of shore activities lets you experience the best of both worlds. Explore the historic core at the colonial village of Battery Point, the Tasmanian Museum and Art Gallery, as well as Theatre Royal, the country’s oldest theater. There’s also wine-tasting and pub-hopping to enjoy. Tasmania’s capital has much in common with Sydney. Founded but a few years later, Hobart also owes its origins to the establishment of a penal colony. It has a dramatic setting like Sydney. Seen from its fine deep-water harbor, Hobart spills over the lower reaches of the Derwent Valley as Mt. Wellington towers in the background. You will find much of the city’s heritage centered on the waterfront. North of the city stretches the vast parkland of the Queen’s Domain.

Port Arthur is named for George Arthur, the Lieutenant Governor of Tasmania from 1823 to 1837. It was Arthur who converted a small convict lumber station on the Tasman Peninsula into the most feared penal colony in Australia. Preserved today as the Port Arthur Historical Site, the then state-of-the-art prison was designed to hold repeat offenders in isolation and hard labor. When it closed in 1877, it marked the end of a dark chapter in English and Australian history. Both Port Arthur is also your gateway to the wild and scenic Tasman Peninsula. Its wave-lashed coast is the site of spectacular rock formations such as Tasman Arch, the Tessellated Pavement and the Devil’s Kitchen. The peninsula is also home to small farms, superb fruit orchards and acclaimed vineyards. The Tasman Peninsula is one of the last refuges for the endangered Tasmanian devil. The Tasmania Devil Conservation Park is in the forefront of protecting these unique – if surly and downright disagreeable – remnants of Tasmanian prehistory.

Kangaroo Island boasts the kind of beauty that will stop you in your tracks. Over half the island is covered with “old-growth” bush land supporting huge populations of kangaroo, koala, goana, wallaby and other native Australian animals. Blessed by vast, open spaces and loads of sun, the “Islanders” raise sheep, create and cellar wines, produce sheep’s milk cheese, distill eucalyptus oil, and harvest the honey of the treasured Ligurian Bee. And there is a thriving art community producing internationally-renowned artwork, woolen items, and crafts. The quintessential seaside town of Penneshaw, where cruise ships dock and ferries come and go, is your gateway to it all.

Sydney, capital of New South Wales and one of Australia’s largest cities, is best known for its harbourfront Sydney Opera House, with a distinctive sail-like design. Massive Darling Harbour and the smaller Circular Quay port are hubs of waterside life, with the arched Harbour Bridge and esteemed Royal Botanic Garden nearby.