For safety reasons, it’s best to join an organised tour rather than kayak independently. Sydney Harbour is a commercial waterway and weather conditions can change abruptly. There are several companies operating from bases on the lower North Shore, Middle Harbour and the Eastern Suburbs.
If you are staying in the city centre the obvious choice is OzPaddle, which is based at Andrew (Boy) Charlton Pool in the Domain. They offer a two-hour excursion, taking in Woolloomooloo, Fort Denison and the Sydney Opera House, as well as to other picturesque sites like Rose Bay. Open to all ages.
If you prefer to go independently, you’ll find several places to hire kayaks, including Manly, Rose Bay, Rozelle Bay, Balmoral Beach, The Domain and the Spit Bridge.
Rose Bay is accessible by bus or ferry, but you may need an Uber or cab to reach the best kayaking locations on the Lower North Shore and Middle Harbour; the Spit Bridge is a particular favourite among kayakers.
Since you are likely to get wet, if not soaked, wear shorts and a tee-shirt or swimwear and a tee-shirt. Take a dry change of clothes. A hat and sunblock are absolutely essential