Hi!
We holidayed there every year between 2006 and 2013 as we had a timeshare apartment at the Porto Bay Residence on the promenade up the hill away from the town centre.
We love Madeira!
We started going as an unmarried couple, went on honeymoon and then took our DS as a baby and a toddler along with aging PIL.
It is not as commercialised as the canaries and it is geared more towards couples (tend to be slightly older - 30+ and families who want the quiet, relaxation of a holiday).
You won't get miles of sandy beaches (some man-made ones) or rowdy drunks, nightclubs or English bars and restaurants that you tend to find in bigger, busier tourist hot spots.
You will get lush scenery, fabulous walks for miles upon miles, mirco-climates, lovely, friendly locals, excellent restaurants (we tended to go where the locals went - it's usually a good indication of a good restaurant), excellent excursions (there is one little water park but it's good for about 2 hours) mainly sea and walking tours and hotels that are mainly 4*+ with a few boutique hotels and B&Bs.
We stopped going due to a growing family and a need to venture to pastures new and have moved, albeit temporarily, onto the AI big, water-park resorts of the Med due to having 2 children with a need to throw themselves down waterslides!
We will definitely be going back when the children are older and can tolerate our pastime fave of walking the levadas and are happy to swim, muck about, read and listen to their music on headphones etc.
But we are tempted to have a cheeky week sometime when the kids are a little older to be left with granny ...