The walk takes us into an area of the Island which has strong literary connections especially in the 19th century when Ventnor in particular was highly fashionable and recommended by Queen Victoria’s doctor for the restorative powers of its climate.
Here’s a summary of the main literary links and some of the authors whose very feet we may be following on what must have been a popular walk over St Boniface Down between Shanklin and Ventnor and also along the coastal path which we will do in the afternoon. http://www.iwight.com/education/literature/literature.asp
Shanklin our starting point was home to Keats for much of 1819 during which he wrote On the Sea. http://www.eecs.harvard.edu/~keith/poems/Sea.html. In particular the Chine which we will pass on our return walk in the afternoon appealed to the Romantic sentiment of the time. (http://en.wikipedia.org/wiki/Shanklin_Chine
St Boniface Down which lies between Shanklin and Ventnor and which towers over Bonchurch and Ventnor on the coast was named after the Anglo Saxon saint http://www.bbc.co.uk/dna/h2g2/A599709 who is supposed to have preached to the fishermen of Bonchurch in the 7th century, before being martyred later by the Friesans, a suitable ending for a Saint at the time.
Charles Dickens said the view from St Boniface Down compared with the Ligurian coastline near Genoa (Portofino etc). Dickens wrote eight chapters in 12 weeks of Oliver Twist while staying at Bonchurch for the first time. He later started David Copperfield at Bonchurch but by this point had rather tired of the Island and did not return.
Even Karl Marx who convalesced in Bonchurch in the 1870s wrote of it that "One can stroll here for hours enjoying both sea and mountain air at the same time".
Hope that whets the appetite.