This is a 7.9 mile country walk with beautiful views across the Isle of Wight and hills with a total elevation of 328m (approx 1100 ft). The terrain is mainly grassy or chalky paths and some road.
I suggest parking at the Historic Dockyard car park near the south end of Queen Street PO1 3GW, cost about £12 for the day. We meet at end of Portsmouth Harbour Station (where the Wightlink FastCat departs) in good time for the 9.15 Fastcat to Ryde Pier Head. This is scheduled to arrive in plenty of time for the 10.03 train from Ryde Pier Head to arrive at Shanklin at 10.31.
The walk then takes us through Shanklin towards Shanklin Down and then to Wroxall. There is no cafe at Wroxall so we need to take our own refreshment. We then continue towards Ventnor turning up to St Boniface Down, the high point of the walk and of the Isle of Wight. We will picnic lunch there before following the ridge back and then down into Shanklin.
We can stop for well earned refreshments in Skanklin before the return train and ferry. The return time is of course flexible but likely to be late afternoon or early evening.
The cost of an open return from Portsmouth Harbour / Shanklin from Trainline is £34.60 at the time of writing although tickets for the ferry and train can be purchased separately from other operators.