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@d0cA
Hi,
First, sounds awesome!! I'm also thinking of cycling to Italy this summer, although probably the other side of August, heading into September (so that the trains home are cheaper and the weather slightly cooler).... You've definitely thought about it a lot more than I have though!
Anyway, I thought I would share my experience from a trip I made last year.
I decided at the last minute I was going to go from London to Barcelona. "Last minute" meaning 1 months notice (at least, that's what I gave work!) but included several weeks that were quite hard (night shifts, long days, job interviews) so there was a lot going on and I didn't really have much time at all to prepare, other than buying a ferry ticket to France. I did, however, manage to rope a friend into the trip with me - I found that invaluable and, indeed, he ended up having a great time (even if he hated it - and me! - at the time).
I can give you more details another time if you require (pm me to remind me to post ;-) but from memory we did about 1500 miles together, from Dieppe to Perpignan/the French-Spanish border. It took us 20 days but we had 5 rest days in that time - the first, a 24 hour period after 10 days of touring, and then 4 days altogether after another 4 days (as we were meeting some other friends who were on holiday in France). I then had a rest of a week (my friend had to go home) before doing the final stretch onto Barcelona on my own.
At the beginning, we were doing about 80-100km/day. By the end (indeed, after the first rest day), we were doing up to 150-160km/day. So don't worry about not being fit enough or anything - you will get there :-) The key point was that we just did 10 miles/hour essentially all the time, so our daily distance was merely a function of how many hours we rode (more as we grew in confidence about camping etc).
Also, in terms of clothes and other stuff, don't take anything! We were lucky to have friends along the way that we saw, so dumped a load of stuff at the first opportunity. You really don't need much - shoes, one pair of socks, one pair of cycling shorts, one pair of light trousers, one tshirt, one longsleeve shirt, a (waterproof) jacket, sunhat, helmet... I think that was about it.
Best,
docA
PS, the mountains actually turned out to be a lot of fun - I didn't need to walk once, but there were times we were very slow (2mph). Just make sure you have a good granny gear and don't plan them too early in the trip (but I can see you have already taken that advice elsewhere)