Cycling (half) the Isle of Wight - Clockwise or Anti-Clockwise?

I cycled it with a group of mates last year.  We turned left out of the ferry terminal.   If you get a shift on, not crazy fast you can get the whole loop including needles and catch the afternoon ferry back to mainland.

I recently had almost the same route you planned. I even then read the information about which bike is better suited on the website http://bestadviser.net/how-to/how-to-keep-riding-in-wet-and-cold-conditi..., here is what I want to say: you better move counterclockwise, you better look at the terrain, and you will discover beautiful valleys. Do not worry about the wind, if the weather is not rainy, it will not.

Just to update this a little. Much of the route around the island has been re-sufaced to the point where tarmac condition is superb.

I did a half Island anti clockwise starting at Cowes, heading out towards the Needles, back East along the military road then heading in land around Chale then heading into Newport via Chillerton and Carrisbrooke Castle. I then used the excellent cycle track that runs along the river Medina to get back into Cowes.

A few lumps to deal with, in all around 700m of climb some of which required getting out of the saddle but it flattened off just when you'd had enough. The final run down into Newtown and then to Cowes was all downhill / easy flat.

Cracked the clockwise route on Sunday. No major snags really. A bit windy on military road but a good day out. Plenty of places to stop en route if you fancy it. Traffic was generally pretty good even with the festival on. 

The Isle of White?  You do my birthplace a disservice sir, with your Isle of bloody White.  If I were of the snowflake generation I would have you banned from the ferry or at least charged double for the on board breakfast.  What's that?  Oh yes, sorry, they already charge double.

I would agree with other posters regarding wind direction advising on which way round you choose to ride.
+1 for the road up to the Needles, two alpine style hairpins if you like that kind of thing.
I would avoid the 'Middle Road from Freshwater to Newport. Too many speeding cars on a narrow carriageway. Use a combination of the minor roads instead, much more pleasant and the scenery is more easily appreciated. You can also apply this logic to avoid most of the Military Road as well. If going anti clock, turn off at Brook and wind your way along the almost parallel minor roads - much more pleasant and less exposed to wind direction.

Its a very sharp climb anti-clock out of Freshwater but you will likely have the wind at your back.

Military Road can be a real slog into the wind going clockwise but views are spectacular and final climb over Freshwater Down is easier. With two of you it will be OK as you can swap turns on the front.

Personally I wouldn't bother heading up to Cowes - I'd go Yarmouth - Newport - Blackwater - Rookley - Godshill - Niton - Freshwater instead. Quite lumpy heading out of Newport.

The direct route (A3054) from Yarmouth - Newport can be a bit fast and intimidating - if you decide to skip doing Cowes take the "Middle Road" via Calbourne instead. Lovely rolling road and great scenery with a fast descent to Newport.

Niton Down clockwise is a long easy climb, like Freshwater Down it is steeper/shorter anti-clock.

If you go as far as Shanklin clockwise then Cowleaze Hill is a real slog, as is the climb out of Ventnor to the Whitwell road.

As Jimmy said, be guided by conditions on the day. Having done it anti-clockwise a couple of times, the road from Freshwater to Nitton is a bit dull east of Brook Bay - but the views west might be better if you go clockwise.

Or you could lop off that SE corner and tootle around the country lanes instead of going straight for Niton and the coast road.

The closed (except to the shuttle bus) road out to The Needles is great

Have only done it once in gopping weather, 80 miles of horriblness. Doing it again this sunday! if I remember I will pop back on and comment.  I went clockwide last time.

Only ever done it once... anti-clockwise. It was raining, and 6 degrees. 

Therefore I can really say much about view, but from my memory, starting from Cowes it was fairly flat for thefirst thrid, then hillier, and then flatter again to finish.

So I'd say let the wind decide your direction on the day.