Portugal in May 2019

I haven't been to the Azores, but I can vouch for Madeira. However, I'd want to spend at least five nights there, which really would cut mainland Portugal short. There's lots more to see there than just Lisbon and Porto. I suggest picking up a comprehensive guide book to Portugal before you commit to spending time flying to an offshore island.

I agree - there's plenty to see that would keep you happily engaged in Portugal for 12 or 14 days without flying to any islands. Keep in mind that adding Azores (or Madeira) or any other island is logistically the same as flying to some other country - it involved all the tasks of getting to/through an airport, a flight (which is not just a short hop), getting oriented at your destination. I'd save the Azores (or Madeira) for another trip. With 12 days on the ground, you can get a great trip across Portugal. Check out the Rick Steves shows on Portugal and pick up his Portugal book - you will find more than enough good stuff to fill 12 days.

Portugal is great, and under-appreciated. You will love it.

I sent you a private message with the link to my Azores guide.

You could easily take a month to visit the Azores (there are 9 islands to choose from) and another month to visit the mainland as well.

I also recommend saving the Azores for a seperate trip, but it could be done visiting the island of Sao Miguel (only) in addition to the mainland. I helped friends make an itinerary starting in Porto, down to Lagos, then Lisbon next, and finishing up in Sao Miguel. It was a busy trip, but they loved it. They said they really liked Porto and Lisbon (actually all of mainland Portugal), but LOVED Sao Miguel calling it “paradise”. They can’t wait to go back to Sao Miguel and see some other Azorean islands as well.

Madeira is another unique and beautiful destination, and deserves at least a week to explore it.

Let me know if you received the link to my guide and if you need any more help.

Carl

I would just see Portugal as there is sooo much to do. Leave Madrid for another trip.
I would add Sintra which can be done as a day trip but I would highly recommend one/two night.
A do not miss in my opinion is the wounderful stunning Pena palace. Bought all my tickets upon arrival from the T.I. at the train station, toured the National Palace and Quinta da. Regaleira that afternoon/early evening. Taxi the next morning at 845am to the Pena Palace entrance standing in the ticket in hand line 30 minutes before the doors opened, bought my shuttle ticket once in at the gift shop and was on the first shuttle to the palace! Outstanding absolutely beautiful!

The tour guides try to push ahead as they use the gift shop to buy their tour groups entry & shuttle tickets.
Be strong and don’t let them get ahead as many arrive after you! Stand your ground!

Both Azores and Madeira are very much worth a visit, although I prefer the Azores.
I would suggest going to Lisbon, flying from Porto and take a few stops in between. The center of Portugal is filled with interesting sites: Alcobaça, Tomar, Nazaré, Coimbra, Aveiro.

If you have time when in Porto you should also go to the Douro valley and Guimaraes.

Thank you all for your wonderful guidance. We have booked our flights in and out of Lisbon. We are thinking that we will do 3 or 4 days in Lisbon with one day being a day trip to Sintra.

We typically rent a car so that we have flexibility to pull off and explore on a whim. I know we don't want to have a car in Lisbon and I am wondering if we should get a car at all but instead just use the train and/or local transportation.

We will go to Porto and explore that area before heading back to Lisbon for one night before flying home.

In between I know there are several areas that we want to explore but I am looking for advice.

Additionally, I have read that you can do a day trip from Porto to Santiago de Compostela. Has anyone done this and would you recommend it?

What are the must do's from Porto.

Thank you for your help.