Heartbreak Hill (The Sydney version for you Boston Marathon types!) is notorious in the Sydney running community. As the most difficult part of the City2Surf race held annually, it is a right of passage when running in Sydney. This is a 10k run one way, including a 2 km steep ascent from Rose Bay to Vaucluse along New South Head Road. To get there, take the 323, 324, 325, or 326 bus line to New South Head Rd near Knox St. Follow New South Head Rd to Rose Bay wharf, which was a seaplane airport during WWII. Here you will begin your climb while enjoying spectacular harbor views, a glimpse of the Bridge and lots of people watching. When you reach the top, follow Military Rd. down to Bondi Beach to take a much deserved swim. Return to the start by taking one of the many bus lines along Blondi Beach.