14 Nights Spain & Portugal

For a more relaxed pace, I would omit Lisbon and Porto for this trip. Allocate those 5 nights amongst your other destinations. For example,
4 or 5 nights in Barcelona
4 nights in Madrid with a day trip to Toledo
4 nights in Seville with a day trip to Cordova
Or at least one night in cordoba
2 nights in Granada

With your current itinerary, you are spending a lot of time traveling to and from destinations but not much time IN the destination.

Wow, from someone that moves at a pretty good clip, thats a lot! You are short time in Barcelona, Sevilla and Lisbon at the very least. Where are you using air travel? I would eliminate Madrid, it is a newer city and has less history than the other cities.

kmkwoo had a good plan, but I suggest a slight change.
4 or 5 nights in Barcelona
4 nights in Madrid with a day trip to Toledo and day trip to Segovia
4 nights in Seville with a day trip to Cordova
Or at least one night in cordoba
2 nights in Granada

We did Portugal in 15 days, just in Portugal that included a week river cruise on the wonderful Douro River, probably the most scenic river valley in Europe.

That's great feedback, thank you!

Bascially, skip Madrid if we really must keep Portugal on this trip. However, if we can come back to Portugal on a future trip (that's where I'm leaning now because that Douro River Cruise and more time in Portugal sounds like the right call), then kmkwoo and geovagriffith recommendations to stay in Madrid - but add two day trips to Toledo and Segovia - makes sense. That way, if Madrid isn't that exciting to see based on it being a newer city with less history, we will be using it 1/2 the days as a launch pad to day trip to local areas that are more interesting. Thanks for the recommendations for day trips, that's very helpful.

I think I'll push Portugal to another year and order the stops as Barcelona, Madrid, Granada and Seville. Thats a little longer train time swapping the order of Seville and Granada, but there are no non-stop flights from Granada to Frankfurt (where we'll be heading next) and there are from Seville.

Any recommended day trips from Barcelona or is our time best spent enjoying that city? I've read about Montserrat, Sitges, Girona and a few others but are there any that you would say are "must see" day trips?

The Douro River is lovely, I think you are making a good choice. When you go, try to stay at a working winery. We stayed at Quinta do Tedo. I loved Segovia and Toledo and Cordoba (and your other places) If its doable, I would always prefer to overnight in Toledo and Cordoba.

The Douro River looks amazing. Do you remember the cruise company you went with and would your recommend them? I'm guessing you need a car in the Douro Valley? There doesn't seem to be much public transportation from Porto into the valley...at least not as far in as Quinta do Tedo.

All your potential side trips from Barcelona are worthwhile. I've never been to Montserrat (maybe on my next trip) but would rate medieval Girona higher than Sitges. The thing about Barcelona itself, though, is that it gets heavy tourist traffic year-round and has a lot of places for which timed entry tickets are required and must be purchased ahead of time because the ticket-buying lines can be very long--and showing up in the afternoon might mean not getting through the line before all the day's tickets are sold out. These are the problem sights I'm aware of:

La Sagrada Familia
Parc Guell
Casa Mila/La Pedrera
Casa Batllo
Picasso Museum
Palau de la Musica Catalana if you want to take an English-language tour

Putting an itinerary together is easier if you can schedule the problem places you want to see (which may not be all of the above) as your first stop in the morning. The fewer days you have in the city, the more challenging that is. If you are unable to do that, you're in the position of having to guess how much of a time buffer to leave between sights, given that you don't know exactly when you'll get inside (later in the day, they may let X people inside only after X people leave), how much time you'll want to spend at each site (the first five will probably be exceedingly crowded), how much time you'll spend traveling to the next site, when you'll want to eat lunch or how long you'll spend doing so. Barcelona is a very attractive city with lots of opportunities to veer off the beaten path to see funky modernista buildings, among other things. There are also quite a few good museums.

There is so much to see and do in Barcelona that you certainly don’t need to take any day trips, and your days will still be filled and very busy, especially because of the timed entry attractions that acraven writes about. Whether or not you have time for a day trip depends on your interests. We spent 6 nights IN Barcelona (no day trips) and we were never bored and we were always busy.

We did spend 2 nights Girona, which we loved. If you do a day trip, I highly recommend Girona.

You are wise to save Portugal for another trip.

We did the Douro River on our own. We had a car. I know Viking does a Douro River Cruise which I believe also includes Salamanca, Spain.

I did the Viking itinerary several years ago. It actually begins with a couple of days in Lisbon with a bus transfer up to Porto (stopping in Coimbra) and included Salamanca as a bus trip from the turn around point on the river. Actually, the whole trip was a lot of bus time to get to the sites from the ports. They were mostly lovely rides, but know what you are getting. It might not be what LexG has in mind.

@HK, the Viking cruise is not what I would have in mind, either. We traveled Portugal on our own. She asked for a cruise company and I knew Viking had one. There are a lot of options for short day cruises or even a train to see the Douro. I'm sure, or I'd at least hope that people take the suggestions and do a bit of research to make decisions. I'm sure you noticed when you signed up for the cruise, that a lot of it is on land. I've only done one river cruise, and picked one with an itinerary that was all River travel.

We looked at the train ride along the Douro, and noted the beginning from Porto is quite dull. At the end of the train ride, there are options to take a day boat ride on the Douro.

The train tracks run along the north side of the Douro River. Pinhao and Regua are on the river (up river)

I think I'll do Portugal via car as that will give me more flexibility in visiting various wineries. Thanks for all the great advice, everyone - much appreciated!!