Buy the Ordance Survey Outdoor Leisure map OL29. It has the whole walk outlined. You'll find coast path signs on the walk, but sometimes they are just not there when you need them. essential Buy the map now on Amazon:

Standard version: Isle of Wight (OS Explorer Map)

Extra durable version:  Isle of Wight (OS Explorer Map Active)

OK this site is a light-hearted look at the walk. I'm not an expert on every nook and cranny. Try the The Complete Isle of Wight Coastal Footpath by B G Smailes. 

For more information on Isle of Wight walks and the coastal path try A walker's guide to the Isle of Wight by Martin Collins and Norman Birch. 

Which way round and from where? This is one of those thorny problems. Planning a walk is part of the fun. I'll let you into a little secret now. I went back and walked part of the path again. This time from Shalfleet to Bembridge. Stopping at Yarmouth, Brighstone and Ventnor. The whole walk was an easy four days and just as enjoyable anticlockwise. All the places on the map are good starting points. Make your own decisions; well your grown up now aren't you?

How far each day? Only you know what you can do. The best way to enjoy this walk is to put as many days in there as possible. My experience is 16 miles a day is about the maximum most people will want to do- a little more, a little less, depending on the ups and downs. For most people five days is enough. It's nice to have a spare day in their - if things go wrong or the weather is dreadful for one day, you will still complete it.

When? Well I'm not an expert on the weather on the Isle of Wight, but my walks are mostly in May, June and July. They tend to be the drier months. One thing the English climate is famous for is its changeability. Go when you please, but remember take the right gear - coast walks are always very exposed to the wind and it's often cooler than in land.

What gear? Well if it's only five days, take what you need not what you would like. I have never read a book once on a walk, listened to a ghetto blaster, dried my hair with a hairdryer etc. Rucksacks full of unnecessary gear become very unpleasant to carry after day one. Travel light. Just make sure the boots are comfortable and fit, rucksacks have a waterproof liner, and waterproof tops and bottoms are in the kit. If you can't fit everything into a 45 litre rucksack - think again.  essential

Blisters. If you don't get them - it means your boots fit well and don't slide around and rub on your foot anywhere. Don't take the chance my advice is take a pack of AMK moleskin's with you.  Apply the moleskin to the areas you have had trouble in the past, or at the first twinge stick them on.  Buy them now at Amazon:  AMK Moleskin     essential

When it's hot.  Start earlier in the day. Walk slower; take the climbs easier. Stop more, for rests in the shade. Carry lots more water with you than you think you need, (you can always get rid of excess, but you might not find more supplies!) and make sure you drink smaller amounts much more regularly.

For more information and an alternative opinion  about the coast path join the Facebook group.