Around the cove from Circular Quay and removed from much of its foot traffic, Woolloomooloo is a local gem with plenty of fine dining options along the waterfront. If it's views you're after, you can't go past China Doll, a stylish pan-Asian restaurant offering fine fare and cocktails in an historic wharf setting. Riley St Garage is where New York grit meets Sydney's fresh seafood: an art deco warehouse famous for its Oyster Bar and raw food menu, with decor inspired by the Meatpacking District. Casual but no less delicious, Smoking Gun Bagels offers wood-fired, Montreal-style bagels with experimental toppings such as wattleseed and peanut butter with macadamia brittle.
From small bars to historic pubs, Woolloomooloo caters to the full spectrum of watering hole experiences. Peekaboo Bar is what would happen if Alice and The Mad Hatter went to a bar: a moodily lit and eclectic rabbit hole with a neat but exciting cocktail list and more atmosphere than you could poke a stick at. On the lighter side, Frisco Hotel is a nautical-themed pub with a rum-heavy drinks menu, daily fresh seafood and endless water views.
Artspace showcases the future of art within an historic Sydney setting. Located in the heritage-listed The Gunnery building—used as a squat by artists through the '70s and '80s—the gallery exhibits work from the next generation of contemporary artists. For performance, Old Fitz Theatre—located beneath The Old Fitzroy Hotel—is at the forefront of Sydney's emerging theatre scene, and is where to discover rising stars after a fine pub feed.