Lisbon, Porto, Madrid

I would include day trips to Segovia and Toledo from Madrid.

If you are as sleep-deprived and jetlagged as I am on my arrival day, you will have only two really usable days in Lisbon, which seems quite short to me.

I don't know whether you're flying home on Day 12 or Day 13, so I'm not sure how much time you have in Madrid. Unless you are a big art fan, you will probably have time for some day-trips.

I would take a day from Porto or Madrid and add it to Lisbon, as your first day at least will be lost to jet lag.

Kayerraga,

I did a Porto-Lisbon-Madrid trip with our 21 year old son in Dec 2017 and offer the following thoughts:
-Loved all three cities. My personal opinion would be that Lisbon deserves the most time and Porto the least time. This of course depends on your interests (for example if you are a wine enthusiast then Porto might deserve the most time);
-It is challenging to get from Portugal to Spain. We took an overnight train from Lisbon to Madrid and it was rough travel (hard to sleep). I think there is also an overnight train to Madrid from Porto. Overnight trains are efficient, but this might be the rare case where flying is the better option;
-While in Lisbon, I recommend at least one day trip to Sintra, which is easily accessible by train. Sintra is very popular (i.e. crowded) so be strategic about your visit there (essentially get there early and have an itinerary in mind before you arrive);
-While in Madrid, I recommend at least one day trip to Toledo or Segovia, which are both easily accessible by train. Personal preference as to which is best, but I preferred Segovia because of its castle;
-Public transportation in Lisbon and Madrid are great. We walked everywhere in Porto because it is small, so I don’t know if Porto even has a subway or tram system;
-We stayed near the center of town in all three cities, which I recommend for efficiency sake;
-Things to Do that I recommend in each city: Porto - port lodge(s), walk across the bridge, boat tour and Harry Potter library (can’t remember the name). Lisbon - Alfa’s tour, Heronimous monetary, Belem tower and tram 28. Madrid - art museums, royal palace, plaza major, Ritero Park).
Good luck and safe travels.

I am planning a trip to Spain and Portugal so in full transparency I haven’t been to these countries yet, but I’ve been researching transportation options for months. After several hours of trying to figure out the best train option from Madrid to either Lisbon or Porto I caved and decided to fly from Madrid to Porto. The flight is an hour and a half and I found tickets for $27. I paid extra to check a bag and reserve seats for a total of $115 for 2 people.

I would add another day to Lisbon. Sintra and Evora are great day trips from Lisbon.

Porto is wonderful. While there do a Douro River cruise or take the train up the river, the scenery is amazing.

While in Madrid be sure and do day trips to Toledo and Segovia.

By the way, we loved Singapore.

Thanks everyone for the help.