Our boats leave from The Spit in Mosman, which puts you at the top of Middle Harbour. The run to Manly takes you out past Grotto Point and across North Harbour — roughly forty minutes at an easy pace, and scenic the whole way rather than a slog to be got through.
That is comfortable inside a three-hour hire if Manly is the main event: out, a couple of hours there, and back. If you want to combine it with a swim somewhere quieter on the way, take the day tripper and stop wherever you like.
North Harbour is noticeably calmer than the main harbour on a windy day, which is part of why this run works so well in a small boat. We go through the route on your map at the briefing, along with where the boat is allowed to go.