Thanks so much for the reply, in looking into it further, I think you are right in just basing the whole time in Funchal – the island is very small and I like your driving suggestions.
I was looking on the far West side more for these Miradouro de Garganta Funda, Miradouro de Ponya Da Ladeira, the Cable Car at Achadas da Cruz, and maybe if foggy, the Fanal Forest.
This might be the new plan:
• Fly in, hire car, drop bags at Funchal where we will stay the whole time
• First day: Do one day of mountains, hiking going from Funchal to Santana (via Curral das Freiras, Pico do Arieiro, Ribeira Frio, Balcoes Viewpoint, Miradouro do Guindaste), to Sao Vicente, then south to Ribeira Brava, then Funchal
• Second day - option one as suggested: (Worried if this is wasting kilometres on stuff already seen though?) Do one day of scenic driving from Funchal to Ribeira Brava (repeated from day before), to Sao Vicente (repeated from day before), then Port Moniz (new), then U-turn back to Sao Vicente (repeated day before, and earlier today), back to Funchal.
• Second day - option two: Do one day of scenic driving from Funchal to Ribeira Brava (repeated from day before), to Sao Vicente (repeated from day before), then Port Moniz (new), then looking at viewpoints along the way to Ponta da Pargo, then maybe trying one of the internal roads (ER110, or ER209 with Fanal Forest on it?) back to VE4 road, back to Funchal. Do you think that would be more interesting?
Do you think skipping the bottom edge from Miradouro de Garganta Funda to Ribeira Brava would be OK then? Not missing anything "must see"? I can see there are some cute fishing villages, and Ponta do Sol pops up on a few people's lists too. You think the other bits are better? I am very excited about the top edge drive, as that looks spectacular, with a dozen Miradouros, a nice vineyard, and Sao Vincente looks lovely to visit (maybe hike up to the Fatima lookout?)