Here's a brief write up on my holiday last week.
Being a bit late with organising things, plans didn't quite work out and I ended up going to Madeira for a week's walking with Exodus Holidays: the hotels were variable but ok-ish, our guide (Leonardo) was excellent, the grade of walks was as expected, and the rest of the group were a good bunch for a weeks' walking.
Weather was typically Madeiran (apparently) - some sun + heat, especially lower down, some breeze, some cloud, and a bit of rain. There were swimming opportunities most days (great for me).
Day 1 Arrival late evening Machico
Briefing, drinks, and bed
Day 2 Ponta da Sao Lourenco
5 miles, approx 100m ascent/descent
This looked easy on paper, and the outward leg was lovely; however, by midday the sun was well and truly up, it was bloody hot with no shade. There was a brief respite with a dip in the sea at lunchtime, but on the return leg I felt like I was cooking. Two ice lollies at the end of the walk helped restore me to normality though I was a bit concerned about how the rest of the week would work out if the weather stayed like this.
Day 3 Machico to Porto da Cruz
8.5 miles, approx 300m ascent/desent
It was a bit cooler, fortunately, as we started with a steep ascent from Machico. After our initial up we followed a levada for a stretch before further ascent over a low pass to arrive on the cliffs on the north coast. An adventurous afternoon followed as we negotiated a stretch of exposed cliff path with a 300m sheer drop to the sea below (this got christened "the path of certain death"). Anyway, after surviving certain death, we bimbled down into Porto da Cruz, stopping for scrumped grapes and figs on the way. The walk ended with drinks and a swim in the surf.
Day 4 The Levada do Caldeiro Verde from Queimadas to Caldeiro Verde then down to Ihla
8 miles, approx 100m ascent/400m descent
The levada walk from Queimadas to Caldeiro Verde is a classic Madeira walk, apparently now made safer (and less adventurous) by installation of rails along the most precipitous stretches, although there are still dark tunnels to liven things up a bit. This is a beautiful walk, but its popularity resulted in hoards of walkers on the way out and at the caldeiro itself. On the way back, we left the main drag back to Queimadas and headed for the village of Ihla in the valley below. Despite the crowds on the outward leg, the forests of laurel, hydrangea, bay, and dandelion trees was wonderful and the "green cauldron" itself well worth a look. 
Day 5 Achada do Teixeira to Encumeada via Pico Ruivo, Pico do Jorge, and Boca Encumeada
9.5 miles, approx 600m ascent/1100m descent
The big walk of the week, and an early start to see the sunrise at Achada do Teixeira. This is another classic walk, with a well-marked trail, but without yesterday's crowds as it really is one for the comitted walker. It was chilly up top, and the view from Pico Ruivo, the highest peak on the island (1862m) was obscured in cloud and drizzle. After a long stretch of steps down and then up a bit more up and down, we ascended toward the top of Pico do Jorge, the way was steep, drizzly and sweaty and brought us to the start of our long descent. After a bit of a chilly lunch stop we headed down - about 2.5 hours descending 1100m in 3-4 miles, mostly on steep and damp rock steps. This was a real challenge for me with my fear of steep descents and slippy steps, but there was time and space for me to plod on without distractions, finally arriving at Encumeada in sunshine to the sound of a buzzard mewing and the distant site of our hotel. Cold beer was followed by a hot bath and a room with a magnificent view!
Day 6 Encumeada to Boca da Corrida following the Caminho Real da Encumeada
8 miles, approx 400m ascent/100m descent
Our last walk of the trip and I was surprised by how well I'd recovered from the day before. Today's walk followed an old Royal Road (a Caminho Real) from Encumeada, heading down a touch to cross the head of the Ribeiro Brava (a couple of almost dry streams) before ascending to a mountain pass above the beautiful Curral de Freiras and then climbing a little more to Boca da Corrida - our journey's end. The walk started off through woodland (eucalyptus and pine) before ascending into scrub of broom and brambles (ouch), with butterflies and spectacular views into the valleys below and of the mountains above. We stretched out along the track and I enjoyed a solitary walk up to the pass. Although the cloud was building in the valleys, the view down to the Curral was lovely. I had a good long lunch break and a lie-down on a rock watching the swifts swooping a few feet above me. I loved this walk!!!
Day 7 R&R day in Funchal
Dolphin watching and lazing by hotel pool for me
Day 8 Back to Blighty
Late morning flight