Planning Portugal trip and need your help!!!
 

We are 2 mid-age couples planning our first Portugal trip in 2nd half of June. We love history, seeing the country, walking tours in the cities, nature, beaches. Here is the itinerary we plan so far but we are very much open to any suggestions on what to see, how much time to plan in each place, what tour to take, what restaurants to eat, which places not to miss!
Fly to Porto
- 2 days Porto - should we plan day and a half in Porto and take half day trip to Guimaraes or plan a day trip to Guimaraes and Braga? Is Braga worth a visit or better to spend extra 1/2 day in Porto? ? We are not religious
- rent a car,
1 day Porto-Pinhao, (sleep in Pinhao Quinta de la Rosa) - what is the best driving route, stops, wineries to visit? Is the dinner in Quinta de la Rosa good?
-1 day Pinhao-Coimbra-Obidos (sleep in Obidos) - should we make a reservation in advance to visit the library in Coimbra University?
1 days Batalha , Alcobaça, Nazare, Tomar (sleep in Pousada in Qurem)
1 day Evora (sleep in Evora) On our drive to Evora we plan to stop in Castelo de Vide to visit Jewish quarter and synagogue and then Marvao. Should we also try to stop at Elvas time permitting or we can skip Elvas? Is Elvas worth a detour?
3 days Algarve ( base in Lagos) - we are thinking on 1 of the days go to Tavira to see the town and then considering to take a 3-4 hours catamaran tour to Ria de Formosa stopping at 1-2 islands with the swimming. Are the beaches here better/more beautiful/calmer/warmer than around Lagos? On the last day we plan to visit Sagres and Cape St. Vincent before driving to Lisbon. Also planning to take a grottos boat tour in Lagos with the swimming.
drive to Lisbon and return a car
3 days Lisbon - 2 days Lisbon , walking tours around the city, Alfama, Belem. 1 day - Sintra - is it better to go to Sintra by train to take a tour? Are there english tours/audio in Monserrat palace/Palacio national/Palacio Pena/Regalero palace?
3 days Madeira - thinking of taking 1 day jeep tour to West/North, 1 day to East and 1 day walk around Funchal and relax at the beaches/pools
Fly to Lisbon and fly home

You might want to take a look at my trip report, leaving out the Spanish side trip to Santiago; click on my name to find it.

There have been a great many discussions with good answers lately - search the forums (top right) by inputting Portugal.

I live in Portugal, and I'll take a few shots:
i- Guimarães is more interesting than Braga, because of the castle and larger old town. Near Guimarães there is Citânia de Briteiros. This was a settlement of pre-Celtic and Celtic people that run from sec IV AC to sec IV AD. Very interesting for someone interested in very old stuff.
ii- Near Coimbra there is Conimbriga, a preRoman, Roman settlement that has been dug up, the villas still have the original tile floors.
iii- Somedays there is a lot of people in line to visit the Coimbra U. Library. To be safe, pre-aarange if possible.
iv- Almourol Castle is close to Tomar and worth a visit if you have the time. But be sure to spend enough time at The Christ Convent.
v- If pressed for time may skip Elvas. If you have plenty of time may extend to Badajoz and Mérida.
vi- The problem with Sintra is that you will need transportation, unless you are physically fit and fond of long walks uphill. English language tours are common, although I cannot guarantee that there will be at all sites. There is at Pena Castle.
vii- in Madeira I enjoyed the day trip to Porto Santo.

FRom my point of view that too much one night. Going to the hotel, checking in, drop the luggage takes precious time.

And you put too much sights in some days :

- Pinhao- Coimbra (2 hours drive). visit coimbra and then go to Obidos (1 hours and half drive). Looks you wont see much of Coimbra.

- ''1 days Batalha , Alcobaça, Nazare, Tomar (sleep in Pousada in Qurem)''....5 places in one day ! Get the car there, park the car do sightseeing....

- 1 day in Evora...that doesnt seems much when you have to take in account the tracel to get there plus the fact that you wnat to see other things on road.

Many people have the same advice: Count the trip by nights. 2 Nights somewhere will give you one full day.

Many thanks everyone for all your advices! Michael, your report is wonderful and very helpful.
moacirdsp, thank you for answering my questions. This is exactly info I was looking for. Is it easy to take taxis in Sintra from the train station and then from one place to another ?

We do not mind one night stays. We prefer them instead of staying in one place and taking day trips. We love towns in the evening when the tours are gone and we can walk, have a dinner and see how local live.
This one of the reasons why we decided not to stay overnight in Coimbra and go to Obidos to stay overnight there - I want to walk around Obidos in the evening, even if it is late. I know that some days are too full , so we are trying to figure out what is a "must" and we can potentially skip if there is not enough time. We are leaving toward skipping Braga and Elvas.

''1 days Batalha , Alcobaça, Nazare, Tomar

Don't. Why the rush?

There are plenty of taxis in Sintra. The Pena Palace is the furthest away..I would consider going there straight from the train station. The other sights are in the downtown area.