Went there a few years ago, loved it. There is only one town, the capital Funchal which has a great market. It is divided into the modern and old town, most of the traditional restaurants are in the old. You can take the cable car up the hill where here are some beautiful botanical gardens and then get the sleighs down (no snow required). It is ideal for walking as all the levadas are mapped out with good written directions, we used the buses to get around, which can be a bit confusing as different companies have the same number bus, but we coped and never ended up in the wrong place. Not much by way of beaches but that did not bother us, I believe some of the smaller places have now been developed a bit to make them more toursity. Temperatures at the beginning of October were still in the high 20's.