Hobart would be your next stop, home of the Cascade Brewery and David Walsh’s Museum of Old and New Art (MONA). The first and last on that list are absolute must-do’s. Any nightlife or shopping will take place on the waterfront by Salamanca Place. Make sure you stop by the Cargo Bar Pizza Lounge for drinks and gourmet pizzas you’ve never heard of. Though on the pricey side, you’ll love every bite.
From Hobart, head to Port Arthur. It’s a bit out of the way but if you’re interested in the history of convicts in Australia, this is where you’ll want to go. Spend a day walking the grounds of the ancient penal colony and take a boat ride to some of the haunted islands just off the coast. A lot of Port Arthur has fallen apart at this point, and much of it is undergoing renovations, but that shouldn’t stop you. I’m not a big history buff but Port Arthur definitely got my wheels spinning. Talk to any of the locals around town and, if you want to save $30, they’ll give you the low-down on how to sneak in through the side. It’s easier than you’d think.