So we have a trip to Portugal planned for late September, and now that we are working on an itinerary, we are strongly considering the idea of dropping the Algarve region and instead spending some time in Madeira. However, we are flying in and out of Lisbon (where I live this seems to be the only option - even flights to Porto basically have you going through Lisbon anyways) and the timing of Madeira flights is not ideal (we would basically have to follow our red-eye into Lisbon by waiting 6 hours until the next flight), so we think the best bet is break it up. Current idea is spend time in Lisbon, then pick up a car and check out Evora, Nazare, Coimbra, and the Douro Valley before ditching the car for a couple days in Porto, then taking a flight to Madeira from there to spend 5-7 days on the island.
I was wondering if anyone had ideas of where to hang out once we fly back to the Lisbon airport for 1 or 2 nights until we have to go home that wasn't just staying in Lisbon proper again. Would there be enough of a neighbourhood to hang out past the daytrippers and spend a night or 2 in Sintra or Cascais? Is there anywhere else in the region I don't know about?