Itinerary Help: Barcelona-Madrid-Cordoba-Seville-Lisbon-Granada

Barcelona needs three nights.
Madrid needs four nights if you include a day trip to Toledo.
Cordoba is a day trip from Sevilla. Give Sevilla three nights.
Granada two nights.
Lisbon four nights and that does not include day trips.
Buy train tickets about two-months out on Renfe because these trains sell out: https://www.renfe.com/es/en. They’re also cheaper the further out you purchase them.

I look at the list of what you want to do in each city and think this trip isn't going to be a lot of fun for you, because you're going to have one eye on your watch the entire time, and you're still going to miss things. You may be able to get to all your targets in Granada (though I'd add the over-the-top San Juan de Dios to the list) and maybe in Seville (though there's more to see there), but in the other cities you have apparently not accounted for the time you will lose moving from city to city or the time required to move from sight to sight within the cities.

In Barcelona, these sights on your list require prepurchase of timed tickets, so you must estimate ahead of time what will be the appropriate gap between entry time and Sight A and entry time at Sight B: La Sagrada Familia, Parc Guell, Casa Mila, Casa Batllo and Palau de la Musica Catalana (where timed English-language tours can sell out). Montserrat is an out-of-town trip that I'd guess takes at least half day (I haven't been there).
To avoid running out of time at Barcelona's sights (whose tickets tend to be expensive), you will need to pad your schedule each step of the way, which will make it especially difficult to cram things in. Don't forget that at some point you must eat. The Spaniards have dinner very, very late (as in after 9 PM or even after 10 PM), so the common recommendation is for visitors to make lunch their main meal--which is what the locals do. If you take that very reasonable approach, you will probably not want to have 10-minute grab-and-go lunches.

This is a very rushed trip, and I really believe you will not find it enjoyable at all. You don't have enough time to visit all the sites you want to see in Barcelona. You don't have time for everything in Toledo unless you mean you just want to walk past some places but not go inside. You need time to eat and I know this sounds corny, but stop and smell the roses. Exploring neighborhoods and coming across the unexpected is just as rewarding as seeing the sites, too.

Also, you don't have as many days as you think you do. For example, in Seville, you have 1.5 days, not 2. Same with Barcelona, 2.5 days, not 3.

Do you have to go to Lisbon? I would drop Lisbon and add those 3 nights to your other existing cities, such as Barcelona, Cordoba, and Seville.

Lisbon doesn't really fit this trip but I see your note that you're meeting a friend there. You have 14 days and 7 cities. I would get rid of 3 cities. 4 cities in 14 days is a better pace for all the things you want to see. It's hard to cut things out - I know - but you'll likely be happier in the end with a smaller footprint for your trip.

As usual, acraven's wisdom is to be trusted. This is lot of ground to cover in 2+ weeks. I doubt that you'll be able to see all that you want to see in Barcelona in only 2 full days, and your jet-lagged arrival day doesn't really count! A day trip to Toledo from Madrid is smart, and I agree that another night in Madrid would be more spacious. But, you have a long list of places you want to see, and I think your expectations of what you can see in Toledo in one day are unrealistic.

In general, I think this is the overall theme of your itinerary. I know this is probably not what you want to hear, but I'm one of those people who subscribes to the "less is more" philosophy. I can spend hours in an art museum (e.g., I would dedicate an entire day to Museo del Prado because seeing beautiful art is a priority for me), but I also recognize that others are ready to leave after an hour.

ETA: I know I'm repeating much of what kmkwoo (and others) said (we were typing responses at the same time). I want to underscore what she said: when you have 3 nights in one place, you really only have 2 days. This is a common misperception, which generates unrealistic expectations of what's possible. There is usually not much you can see or do on your arrival day in any given place (e.g., if your train arrives at 4 pm, that leaves you little time to do much other than walking around your neighborhood before you figure out what you'll do for dinner).

As you can see, there are many members of the chorus encouraging you to slow down and immerse a bit in any given place so that you can enjoy your travels. Any chance you can extend your trip by adding some extra days?

¡Buena Suerte!

To get another reality check about how to pace yourself while seeing the many Barcelona sites on your wish list, you might find this recent thread to be helpful:

https://community.ricksteves.com/travel-forum/spain/time-necessary-in-park-guell-and-gaudi-buildings

I am not married to my itinerary so I have two questions to pose to
you all:
1. What cities would you eliminate?
2. What activities would you eliminate?

Well, the real outlier here is Lisbon because that falls smack dab in the middle of a trip to Spain. Even though your Lisbon-Spain flights are short ones, you'll lose the better part of those 2 days to travel. But, Lisbon is the one city that seems to be a must for you given that you're meeting a friend.

It's unclear whether you've already purchased your air travel. If not, I would start or end in Lisbon because flights in or out of Lisbon should be easy (using the multi-city option for booking flights). If you've already purchased your RT flights, I would eliminate all points south of Madrid. Not because I think Granada or Sevilla are not worthwhile, but because you've sketched out relatively short stays in each place, and your transit time to and fro will significantly eat away at your limited time when you could instead be enjoying the places on your wish list in other parts of Spain.

Save Granada and Sevilla for another trip. This is what I mean when I say "less is more." I know these are hard choices. As the good book says, "assume you will return."

Also, whether you start in Lisbon or Barcelona, I would strongly suggest staying a bit longer in that first city upon your arrival, so you can recover from a long flight. For example, I usually stay in my first arrival city for at least 5 nights, not only to recover from jet lag but also to spend quality time in that fabulous city. That is my personal preference, but you may be more resilient than I am.

Thank you everyone for your feedback thus far! It is exactly what I came to this forum for. I am not a very slow traveler, and tend to pack my trips (a shoutout to the London-Paris-Edinburgh-Amsterdam-Munich-Vienna-Prague gauntlet I ran through in approximately one month).

I should have mentioned that I am not planning to visit all of the attractions I'm interested in. I plan to cull the list out and just plan to visit again in the future!

I've considered the responses here, and think maybe I will pivot to do:

Day 1: Arrival in Barcelona
Days 2 - 4: Barcelona (Day Trip to Montserrat)
Day 5: Barcelona → Sevilla
Days 6 - 9: Sevilla (Day Trip to Cordoba)
Day 10: Sevilla → Lisbon
Days 11 & 12: Lisbon
Day 13: Lisbon → Madrid
Days 14 & 15: Madrid (Day Trip to Toledo, optional)
Day 16: Departure from Madrid

I think at this point I'm okay with this itinerary, and will begin planning and eliminating activities. Only question remaining is if it will be worthwhile to take the train versus flying.

@MaryPat: Appreciate the simple suggestions! It helped me sort out a couple of options, and consider that I could utilize Sevilla as a home base for day trips. Seems silly, but I was oddly married

@kmkwoo: Lisbon is the one city that is not negotiable, but I hear you on the Barcelona, Cordoba, and Seville recommendations. I tried to keep these three cities, and it seems that the rest of Andalusia will have to be a trip for another day.

@Valerie: I appreciate the simple recommendation on the upper limit. I revised my itinerary in consideration of it, and I thought it helped a lot!

@Lynne with an e: Thanks for the more detailed feedback, and the link to the other thread! I haven't gotten to that step in my planning yet, so it was useful.

I could expand my trip for approx $400 extra by three days (to get a full Thursday, Friday, and Saturday--then fly out Sunday). This is a doable option, but with my adjusted schedule, it would then be:

Days 14 - 18: Madrid
Day 19: Fly out of Madrid

It would give me more time to fit in the Toledo trip, but I'll push up against my need to return home by Monday and am unsure of the value add of three extra days in Madrid. I probably would do it in a heartbeat if I could arrange to add those three days to Granada, but it doesn't seem reasonable without rushing between Barcelona-Sevilla-Lisbon.

Your revised trip looks fine to me, but Lisbon is a tough one--that's a lot of extra flights to pack into a trip considering you have the long trek of Barcelona to Sevilla too, but I don't see any way around it.