A day that stays within half a mile of the water and covers eight centuries.
Morning: the Quay and the museum
Start on Poole Quay, where the trade that built the town actually happened. Poole Museum is a few steps away, free, and holds the Poole Logboat, an Iron Age vessel recovered from the harbour mud.
Late morning: the Cockle Trail
The marked trail runs through the Old Town, linking the Guildhall, Scaplen's Court and the Georgian merchant houses. Flat, free, and roughly ninety minutes with a group.
Lunch
The Old Town and the Quay between them have more than enough. See restaurants and pubs and bars.
Afternoon: out on the water
A harbour cruise puts the whole town in context from the water. See boat tours, or extend to Brownsea Island if the day allows.
See the history of Poole for the background.