Portugal and Spain in 2 weeks by train

Hello, I think you need to take a big step back and really consider your itinerary, 7 sight rich cities in 14 nights? That leaves you an average of 2 nights in each, which is really lacking especially in places like Barcelona, which I usually recommend a minimum of 3-4 nights. Ground connections between Portugal and Spain are also sparse, I know it's easy to lump the two countries together, but unless you have 3+ weeks, it would not be efficient to visit the major cities of Spain and Portugal all on the same trip. I would throw the Eurail Pass idea out and try to focus on one country.

What do you like to do?

More details would make it easier for folks here to share advice.

Also, everything Carlos said is spot-on.

Carlos' comments are spot on! I would recommend that you drop Portugal and use your two weeks to visit Spain. As for France, where does your son wish to travel in that country? Remember, Paris is 8 to 11 hours by train from Barcelona.

It looks like you are flying in Madrid and out Barcelona. As stated, drop Portugal. There is a bus from Lisbon to Seville, but most fly.
Madrid - 3
Salamanca - 1
Sevilla - 4
Malaga - 2 (but I would replace Malaga with Granada....and be sure to book tickets to the Alhambra asap)
Barcelona - 4
This is just a shot in the dark and you need to look at it from your specific dates and number of days on the ground - not the day you leave Montreal.
Please consider we are just fellow travelers willing to help, not design. If you wanted to see these places you must have a reason why, so branch out from there. A good guidebook is going to help explain what to see in each and you can decide from your research how long and what to see.
I tend to recommend Lonely Planet 'on a shoe string' guide books; particularly for novice young travelers. The two of you can share it for this part of the trip and your son can then take over and use it to plan his France portion.
A guidebook used at least once in a person's travel life outlines all you need to know to plan for future travel...in my opinion.
If you have already purchased the Eurorail pass, then I hope it works for you. The Man in Seat 61 is the prime go to source for all things train. Here is his explanation on the pass https://www.seat61.com/Railpass-and-Eurail-pass-guide.htm Use the site to see about how to get from A to B or from Barcelona to France.

Thank you all for your replies. We will stay in Spain for the 2 weeks as you all recommended. As for the 3rd week, my son hasn't made his itinerary yet. He would like to visit France. Could you give recommendations?

Maria, thank you for recommending the Man in Seat 61 site, very informative and useful. Also, we'll get the Lonely Planet book :)

@cerecth - It really depends on what your son is interested in seeing in France... Cathar Castles? Roman Ruins? Impressionist art? The beach (depending on weather)? etc. It also depends on when he is planning to go?

As a starting point, since he will be in Barcelona, why not a little road trip trough northern Catalonia and the neighbouring Languedoc region of southern France, ending up back in Barcelona?

Also, since you will no longer be traveling to Portugal, may I suggest reposting your Spain and/or France travel questions in their respective travel forum sections, to get the most responses.