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The Cheeseburger Run
Sawtell to Coffs Harbour (video shows big swell and significant beam waves at times)
Nobbys
Norah Head has a protected launch for NE swell/wind (Soldiers Beach), Terrigal has a protected beach
Surf
Surf
Surfski.info discussion of Sydney downwinders - traffic can be one of the biggest problems for Sydney downwinders, causing even short runs to take up a lot of time with the shuttle. Parking - “you're best with 3 council stickers, Pittwater, Warringah and Manly. A bit of an investment but worth the hassle free parking.” or find shuttles with clubs or self organized groups - look at “Services” below.
Many of Sydney's beaches are proper surfing beaches with good size breaks. But there are major passages (bays, estuaries) that allow one to get out on the open ocean without having to negotiate the shore breaks. The Sydney coast line does have a number of headlands and steep shorelines that can generate significant rebound closer to shore. Sydney surfskiers therefore can choose to practice getting through shore break (or not) and they often learn to handle downwind waves that bounce around with rebound.
One Sydney paddler's take on local open ocean paddling (around Malabar into Botany Bay).
(North to South, the Sydney area has many surfing locations, some appropriate for prepared surfskiers - the following list is just spots where we have videos)
Surfski surfing Bundeena
Flatwater
Todd Borland in Revo (possibly Kiama - Wollongong)