Diamond Harbour
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Though geographic neighbours, and similar in terms of landscape and geological origin, Port Hills and Banks Peninsula are worlds apart. The former is relatively easy to access and boasts an extensive network of good, dog-friendly walks. The latter is much harder to get at - and when you manage to do so, it is a constant frustration because of the limitations on where you can take your dog.
Diamond Harbour sits between the two. Though technically on Banks Peninsula, it seems to 'belong' to the Port Hills. It nestles on the edge of Lyttleton Harbour and stares at Lyttleton itself, only a kilometre or so away across the water, while being more-or-less cut off from Akaroa and the rest of Banks Peninsula to the south. And yet, in terms of dog-walking, it just doesn't quite come up to the hills to the north. Though there are a number of rewarding walks in the area - notably the route up Mount Herbert - the majority are off limits to dogs, and even the few good beaches on oiffer are non-dog for much of the year. The one dog-friendly walk of any length is the Head-to-Head walk. (Note that this is one of three Head-to-Head walks around Lyttleton Harbour; presumably the intention, one day, will be link them all up!) This runs from Hays Bay in the north-west to Purau beach in the south-east. For a full walk, it's probably best to start at Hays Bay and walk east. For a slightly shorter walk you can also join the walk ifrom Black Rock Road a little tothe north, but to do so you have to brave a daunting forest of private road signs on the headland, which seems to have been taken over as one of those dreadful gated communities. Another option is to access the walk from Stoddart Point Reserve in Diamond Harbour, more-or-less in the centre of the walkway. 
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For the most part the walk is pleasant and not too demanding, with a varied terrain of rocky headland, pine forest and sandy beach. The views towards Lyttleton are good, and to whet your appetite to head over there, you pass the jetty from which the small Lyttleton ferry leaves. On Stoddart Point there are some shady picnic spots, and a cafe/bar is nearby. As you continue on around the headland, however, the track becomes narrow and in places has an uncomfortable cross-slope that means you need to be reasonably sure of foot. Some of the signage is also annoyingly ambiguous, so it can be easy to miss your way. It's worth bearing in mind, as well, that the final section down to Purau is on a narriow verge by the road. When you see the side-path signed to Purau Avenue you might therefore be tempted to cut the walk short and head back up into Diamond Harbour. Be warned, though: it's a short and rather precipitous scramble up to the road - and I definitely wouldn't advise this as a way of joining the path from above.
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To make the walk into a round trip, from Purau you can take Waituturi Lane and the Old Stock Road up to join Bay View Road - a small, gravel track - and then follow that back to the start at Hays Bay. There are also several options to walk down through Diamond harbour to the southern end of Stoddart Point (see map below).
Whatever route you choose, this is a worthwhile walk but it has its hazards - so take care!
Whatever route you choose, this is a worthwhile walk but it has its hazards - so take care!