We had such a wonderful, unstructured exploration of Madeira. We rented a car and drove around the tiny, death-defying roads that twisted and turned through the mountains. Here are our recommendations and the itinerary:
Hotel
Porto Del Mare: A beautiful resort within walking distance of Funchal. The grounds were immaculate and we just wished we were there in nicer weather to enjoy more of the pools / sun loungers. Also - breakfast was fab! ($200/night)
Restaurants
Restaurante Doca do Cavacas: This cliffside restaurant outside of Funchal has amazing views. We went late a night so the view was of glimmering lights, but it's supposed to be fabulous at sunset. We enjoyed the grilled calamari, praws, and octopus. The white wine from the island is fantastic!
Med Restaurant: We rarely go to hotel restaurants, but this restaurant in our resort was in the top 10 on Trip Advisor. The atmosphere was lovely - intimate and well decorated. The food was beautifully presented...P loved the Tuna and the dessert was stunning
Things to Do
Up Mountain Jeep Tours: We did an amazing half day tour around the island. It's a very small tour - and you stand in the back of an open air jeep driving up crazy, off road paths around the mountains. It was highly enjoyable and we never would have been able to see these spots without the tour. It's inexpensive and fabulous
Ponta de Sao Lourence: This was a wonderful 2 hour hike - we only got about half way through the path before it began to get dark. If you want to do the whole hike, it would take about 5 hours -- it was moderately strenuous - definitely bring sturdy shoes, but you don't need to be an expert hiker.
Monte's Palace: There are two botanic gardens on Madeira. This one was beautiful - tropical with a beautiful orchid garden, oriental decoration, and waterfalls. My only regret was that we didn't take the cable car up...the road to get there was insanely dangerous. Also, suggest arriving when it first opens...cruise ship hoards seemed to arrive around 12:00 pm
Porto Muniz: This is about an hour from Funchal, the city is neat with all kinds of calm lava pools. If you were there in the summer it would be a great place to swim, but in the winter, it was a lovely spot for photos. Along the path to Porto Muniz, there are many beautiful spots to take photos!

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