Thank you Acraven & Chani! Both of you made great points. I'd be doing the trip next month.
What if I leave Lisbon out on this trip. That would free up 2-3 days so now I'm thinking:
Fly into Barcelona ( Sept 20 land around 12:30p - Sept 24 so 4 nights)
Fly Barcelona to Porto ( Sept 24 - 28 so 4 nights)
Fly out Porto to Madrid ( Sept 29 - Oct 3 so 4 nights)
Fly out home Oct 3
I picked Porto over Lisbon because I read Porto is more laidback which I think I'll like and think it'll be nice to have a laidback period between Barcelona and Madrid.
Realistically, I plan to do 1-2 ticketed events at each of those place. I'm more of a laid-back person and just like go with the flow and figure things out. I like to admire beauty from the outside and be present instead of dealing with the stress and anxiety of getting tickets and having to be on time and locking myself into a future commitment incase I rather do something else at that time.
My nightly budget for hotel is €200-225. I prefer not to do hostels and do a hotel. Preferably, with a rooftop bar or where young adults stay (30-45 yr olds). I did see if I wait to book the hotel closer to the date (like a week or so out), they tend to be a little cheaper but I also know it is a gamble. Good thing is that it's just me so I can be flexible and book something last minute as long as it is in a convenient, safe area/hotel.
As for restaurants, I eat very little so portions aren't a priority and actually prefer smaller meals. Also, I don't eat seafood either which I know Portugal is known for.
I also plan on having a carry-on and a backpack but not sure if I should do like a 35L backpack and a duffle bag so I have room to bring back things. Thoughts on that? I think the latter will be easier to travel with between cities.
Thank you again!