Itinerary help - 2 Weeks in Portugal & Spain

Hi Angela, This is tough to advise at this point...I have been thinking of the best way to help since you first posted but my first question is what city are you flying into and where will you be departing from? Many travelers recommend www.rome2rio.com for transportation options and I like it as well. I have not visited Madrid or Salamanca, but I have visited the other cities. Are you 100% sure about not renting a car at any time? So as not to confuse you in any way, I will hold off on any ideas until you re-post with answers on my questions. Take care!

Sintra and Cascais are quick and easy day trips by train from Lisbon. (Separate day trips--not both in one day.) So, you can base yourself in Lisbon for some of your time in Portugal and see Sintra and Cascais, as well. We had 5 nights in Lisbon and did this and saw plenty of Lisbon, as well. We then flew to Madrid from there, and didn't go to the other places in Portugal or Spain you mention, so I can't speak to those.

The Lisboa card will not only cover some of your admissions in Lisbon, but will also cover your transportation within Lisbon and trains to Sintra and to Cascais (but not the bus within Sintra--you need to purchase that separately in Sintra). It's good value, unlike some of the city cards elsewhere, because it does cover those day-trip trains and it expires the specified number of hours after you start using it (unlike many other places, where the card expires at midnight on the last full day no matter what time you started using it). So, we were even able to use our card for transportation to the airport on the last morning and then handed it to another couple who was arriving, because it still had 4 hours on it.

Thank you so much for the information! It looks like we will fly into Lisbon and fly out of Madrid. Do you recommend taking a train from Lisbon to Madrid, or is a flight easier?

Last year, I went on a pre-adventure with my collage aged daughter before dropping her of at the University of Salamanca.
Here was our itinerary:
Flight to Lisbon. 4 days - including the Belem area and Sintra.
Train to Porto.
Train to Coimbra.
Bus to Salamanca.Ticket could only be paid in cash.
Said our goodbyes. On my own. Bus to Madrid. Bus to Granada. Loved this place. Bus to Seville. Awesome town. I happened to be there for their Feria. All the beautiful outfits, WOW!
Then back home.

The buses were interesting. From Coimbra to Salamanca. No bathrooms on board, but made several stops.
To Madrid, very cramped, no bathroom, and no stops.
Total luxury to Granada. Bathroom, food and free headphones for the tv screen. It was just like being on an airplane. Even had a "bus"attendant. Last ride to Seville was quick, sorry that's all I remember.
Hope this helps!
Enjoy your adventure!

Knowing your arrival and departure airports, I would Start in Lisbon and visit the surrounding areas, fly to Seville, fly to Porto, bus to Salamanca, and train to Madrid to finish the trip. Flying from city to city is more expensive than any other means of transportation for 4 people, but will save time. Probably 98% of the information you need including the must sees are in the Portugal and Spain guide books. As an alternative itinerary, I think start Lisbon (and surrounding areas), train to Porto, bus to Salamanca, train to Seville (change in Madrid), then train back to Madrid to end the trip. Travel between Portugal and Spain without a car is not a strong point of mine, so I used the rome2rio website for guidance. Good luck and I hope you have a spectacular trip!!