In reply to fiddaz:
Leave your rack at home.
Might be worth throwing in boot & chalk bag.
A DH rig would be a much more productive thing to take.....
The hi level walking is great and the scenery quite amazing. Some of the levadas (off the beaten track and in poor repair) can be pretty necky in places.
We really liked the north coast much more than the south coast around Funchal.
And keep away from the crinklies!
And I've never had a hire car in first gear more time than we did on the crazy Madeiran roads. Watch out for the locals, they drive by a different set of rules to sane people .....