Sydney offers an exceptionally diverse paddling environment, encompassing the iconic Sydney Harbour, sheltered creek systems, national park waterways, and coastal inlets spread across a large metropolitan area. The range of conditions suits everyone from beginners to experienced sea kayakers.

Sydney Harbour is the centrepiece of paddling in the region. Launching points include Clontarf Reserve, where free parking is available on Monash Crescent, McMahons Point near Blues Point Reserve (with approximately four hours of free street parking), and Rose Bay in the Eastern Suburbs. From the harbour, paddlers can reach landmarks including the Sydney Harbour Bridge, Sydney Opera House, Taronga Zoo, Bradleys Head, Luna Park, Goat Island, and Fort Denison. The harbour carries significant boat traffic, and paddlers should be aware of ferries, recreational vessels, and wash from larger craft. Middle Harbour, accessible from the Spit Bridge in Mosman, offers dramatic cliffs and waterfront architecture with a more sheltered character than the main harbour.

For calmer, more protected paddling, Lane Cove River within Lane Cove National Park is a popular option close to the city centre. Tides and currents are not a significant concern there, and the surrounding forest provides wind shelter. The Cottonwood Glen picnic area serves as a launch point and includes parking, picnic tables, and toilets, though a national park entry fee applies.

Berowra Creek, accessed via the Dust Hole Boat Ramp at Berowra Waters Marina, offers free parking and a café nearby. Paddlers should monitor tides carefully, as currents can be strong, particularly in the northward direction where the creek widens. Cockle Creek at Bobbin Head is another sheltered option within the national park, notable for its eucalyptus forest surroundings and orange-yellow sandstone cliffs. Powered boats are not permitted on Cockle Creek, and paddling at low tide should be avoided as the water becomes too shallow. The Bobbin Head picnic area has a designated canoe launch point at its southern end.

Pittwater on the Northern Beaches, roughly 40 kilometres north of the CBD, provides extensive waterways including access to Scotland Island and beaches reachable only by water. Manly is another well-regarded location with generally calm conditions suitable for a range of skill levels, and kayak hire is available directly at Manly Wharf. The Nepean River in Western Sydney offers a bush paddling experience and flows toward the Hawkesbury River.

Guided tours operating on Sydney Harbour typically run at sunrise, mid-morning, and sunset, catering to various preferences. Wildlife of interest includes water dragons along Lane Cove River, fairy penguins at Store Beach near Manly (generally present between May and February), and seals viewable from the water near Palm Beach.