My wife really, really wants to go to Portugal this year and unfortunately due to other circumstances, we can only go during the end of the high tourist season (mid-August to September). We'll also be traveling with our son who will be 18 months old at that time. There is so much to do and see in Portugal that I'm getting a little overwhelmed with the planning. Because we'll have our son with us, I don't want to move at too frenetic of a pace around the country, but I would still like to see as much as possible without returning home regretting that we did not see, explore and absorb the culture enough.
I'm also strongly considering renting a car for most of the long distance traveling and we'll probably use public transportation (bus/trams/trains) within the cities we stay in and even possibly for day trips.
Places we want to see (although it may not be realistic with the time we have) are below. Any help/suggestions on things we SHOULD/NEED to see and things that we can probably skip out on would be greatly appreciated. Also, suggestions/recommendations on how long we probably should stay in each location.
Planning on flying in/out of Lisbon and contemplating using Lisbon as our main hub for most of the entirety of our stay (to save on dragging around all of our luggage everywhere we go for overnights).
1. Lisbon (4-5 nights???)
2. Sintra (day trip from Lisbon)
3. Evora (day trip from Lisbon)
5. Porto/Douro Valley (2-3 nights???)
6. Madeira (one of things we're both really looking forward to) (2 nights???) (fly in/out from Lisbon)
8. Evora (1 night??)
9. Back to Lisbon
Thanks and appreciate any help that I may receive!