hiya mate ten years ago or such me and two mates set off from workington to cycle c to c in a day! yeah i know we were stupid. we had one of the lads track us over the route with food, drinks, spares etc. We did it in one day coz we couldn't get time off work.
Got lost a couple of times. we picked the longest day in summer to do it! Whilst outside the highest pub in england on the penines it was pissing down. That was one of the coldest times in my life cycling downhill in the rain for miles. We finally arrived at the east coast at 9pm after leaving at 7am. it was fucking stupid!! great views, great country but my arse hurt for a week. it was all about mental strength. only two of us finished it! 164miles later
Be warned do not follow my lead!
It would have been great to do it over a few days. There are places to stay along the way on the various routes and cafe/pub stops which are well documented. You will love it done over a few days, say 50 miles a day. we had a booklet and it did suggest booking b and b's before hand. if you can take tents you are sorted.
every englishman should do it before they die, the landscape is as beautifull as anywhere in the world!