Some cities have squares or plazas. Dunedin is a little different, with its 8-sided Octagon, encircled by Moray Place. Start the day by checking out the Dunedin Public Art Gallery and the grand St. Paul’s Cathedral. A short walk from the Octagon is the photogenic Dunedin Railway Station. If you happen to be in Dunedin on a Saturday, spend some time wandering around the farmers market outside the train station. Walk north up George Street for lunch, stopping at local boutiques and gift stores along the way.

The University of Otago is a major part of Dunedin life. After lunch, take a stroll through campus. Look out for the attractive clocktower building and the Quad, which has stood in for universities such as Oxford and Cambridge in films. Continuing north, make your way to the Dunedin Botanic Garden en route to Baldwin Street—said to be the steepest in the world. Climb to the top if you have the energy, or just look at the houses and cars perched there at odd angles.

Loop back to where you started the day, and have dinner in the Octagon. If you’re in town during the summer, sit streetside and enjoy the long, light evenings; otherwise, cozy up next to a fireplace. Despite its small size, Dunedin offers something to suit almost every taste—besides grungy student bars, you’ll find microbreweries, fancy cocktail bars, and wine bars selling fine Central Otago pinot noirs.