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Click Travel Map to reload or see full size. Courtesy of Travellerspoint

I've been twice in Madeira. For the first time we only visited Funchal, and a couple of towns around - Câmara de Lobos, Estreito, Machico and travelling by bus in the (dangerous) old road, Porto Moniz.. In the second visit, renting a car and using the modern highways and tunnels, we might easily add Ribeira Brava, São Vicente, Seixal, Paul da Serra, Encumeada, Serra de Água, Santo António, Santo da Serra and the wonderful sightseeing points of Pico de Areeiro and Portela.
A third visit is not impossible but... it's nice, but it's seen.
Câmara de Lobos
Eira do Serrado
Encumeada
Estreito
Funchal
Paul da Serra
Portela
Porto Moniz
Rabaçal
Ribeira Brava
Santana
Santo António
Santo da Serra
São Lourenço
São Vicente
Seixal