Rough charm meets aspirational luxury in Woolloomooloo, one of Sydney’s most rapidly evolving suburbs that is truly a tale of extremes. Bordered by the Garden Island Naval Base, Sydney’s Botanic Gardens and the spectacular Andrew Boy Charlton outdoor swimming pool, Woolloomooloo’s extensive council housing and hostel network is flanked by the Finger Wharf, one of the most expensive waterfront residential developments in Australia. The interplay between its salty dockland history and its recent gentrification is a dynamic and defining character of the horseshoe shaped valley, which dates back to colonial times. Today fine dining and fifty foot yachts abut historical cottages and a much-loved pie cartin the suburb that also includes one of Sydney’s most interesting theatres, The Old Fitz, and contemporary art gallery Artspace.