Thanks to Maurice who has let me know that the Portal NetMadeira has added four new webcams that have come online in Funchal. One overlooks the bay, one overlooks Barreirinha, one looks south and the 4th looks north. Great to see more Webcams on the island.
The Summer has not been that great for many areas the last few weeks, The north and east of the island has really suffered with dark clouds and rain, I can see from Caniço de Baixo the huge cover of cloud affecting the east, and from the airport onward they have had plenty of rain and low cloud. Funchal has also suffered with this low cloud that seems to build up during the day.
If you are looking for Sun hen west of Funchal seems a god bet, and anywhere higher up, the peaks, Paul da Serra and anything over 1200 meters seems to be enjoying the sun, and you get to look out over the ocean of cloud as you are above it.
The webcam at Calheta seems to be out of action, I guess where its situated is out of action, it will be good if they get this fixed soon, but the weather that side seems to be great and cloud free, as friends have told me.
So you can check out all the webcams round the island on the link below, I believe they are updated every 10 minutes.