Clockwise would be the best direction, especially if you go via the road from Shanklin to Ventnor, not on the official route but a better, if hillier, option IMO.
Be prepared to change the direction of travel if the wind is strong and from the west, the section between Blackgang and Freshwater, whether on the main coast road or the back lanes that run parallel, is very exposed. If the wind is strong it's a battle into it all the way to Freshwater, in which case going anti-clockwise would be better.
As for nammit, there are loads of good pubs with beer gardens so you can sit in the sun* and admire your bike** as you eat. Off the top of my head, some handy for the coastal roads-
White Mouse, Chale
Horse and Groom, Shalfleet
Woodvale, Gurnard
Bargemans Rest, Newport
Folly Inn, Whippingham
The Buddle Inn, Ntion
The Spyglass, Ventnor
Steamer Inn, Shanklin
Plus endless cafes, shops, takeaways etc. You're never far from somewhere to get food on the Island.
*It's always sunny on The Island
**I find no better accompaniment to a meal than the sight of the sun reflecting of titanium
