hi i have been walking in madeira for the last 15 years &@ all times of the year,in september shorts are fine for most lavardas but look out for blackthorne it can cut your legs.ALLWAYS take rain proof clothing with u, as u can get heavy rain,sleet,fog,and hot sun all in 1 day.the woolen cap may be cheaper to buy in funchal market near ski lift.the walking in madeira is sensational, if u have landscapes of madeira i could point out a few walks. regards tony.