Lisbon-Barcelona - but what in between?

I have been to Madrid and Toledo but not to Seville and Granada. I enjoyed Madrid and Toledo. Madrid and Barcelona are very different cities and I like the contrast. I am going to Seville and Granada next month for the first time. With your time, I would recommend spending three nights in each location like this:

Thursday - Arrive in Lisbon
Friday - Lisbon
Saturaday - Lisbon (maybe a day trip somewhere on the coast?)
Sunday - AM flight to Madrid
Monday -Madrid
Tuesday - Day trip to Toledo
Wednesday- AM train to Barcelona (much easier than flying and only a shade over 2 and a half hours)
Thursday - Barcelona
Friday - Barcelona
Saturday - Fly home

You could swap out Seville for Madrid (and see Cordoba as a day trip) as there are direct flights there from Lisbon. Seville is smaller than Madrid so that might be more analogous to Florence for you. For flights from Lisbon, check skyscanner.net. For the train between Madrid and Barcelona, check Renfe.com. If you decide on Seville rather than Madrid, i would consider flying to Barcelona as the train takes about 6 hours.

Thanks, Stephen. I would love to hear your thoughts after you come back from Granada and Seville. We have time before truly deciding...and I've had a hard time finding someone who's been to all of these places.

All of the cities you mention I have visited, and I liked them all. They are all worthwhile. My biggest worry for you is how many days you have for this trip. For what it is worth, I think Madrid deserves 3 days, Toledo one day, Sevilla two days, and Granada 1-2 days. Please note that you could easily spend more time in all of them. For example, I have been in Madrid several times, and I am still learning the city. One thing to be said for Sevilla and Granada (and Sevilla especially) is that they will give you a very different perspective on Spain; the south of Spain being quite different from northern Spain, and especially different from Barcelona.

jeff

I agree with the final comments of the earlier two participants here, and would advise you to include Sevilla rather than Madrid. Lisbon, Barcelona and Madrid are all very large cities, while Sevilla is somewhat smaller and more easy-going, with a different Andalusian personality. I loved Sevilla, and found Madrid OK but not unique. With only nine nights, you might also just divide your trip into two parts, Lisbon and Barcelona, perhaps with day trips to Sintra from Lisbon, Girona from Barcelona, etc. that would be less rushed and involve less packing up and traveling, which even with short flights would eat up an extra half-day or more.

Madid and Sevilla are interchangeable - decide which appeals more.
Granada, I think, is not possible with your limited time. Cordoba, however, is a possibility from Sevilla.

Thursday - Arrive in Lisbon - 3 nights
Friday - Lisbon
Saturday - Day trip to Sintra
Sunday - Fly to Madrid or Sevilla - 3 nights
Monday - Madrid or Sevilla
Tuesday - Day trip to Toledo or Cordoba
Wednesday - AVE train to Barcelona - 3 nights
Thursday - Barcelona
Friday - Barcelona
Saturday - Depart from Barcelona

You have 8.5 days. Thursday in Lisbon is only 1/2 day - it'll take time to get through the airport, into the city and to your hotel. And you'll be jetlagged and probably won't sleep that much on the plane, even a night flight. You'll use 1/2 day to fly to Spain. That leaves you 8 days, only 7.5 if you use 1/2 day from another city to Barcelona.

How much time do you want to spend in Portugal? Do you want to visit Porto? It's usually easier to return to Spain than Portugal, so I'd recommend using enough time there, then see if you have time for anything in Spain before Barcelona. BTW I've been to all your places of interest except Portugal.

Most of central Madrid is 19th century. As a city, it is not as impressive or interesting as other Spanish cities with longer, more varied history. It has some of the best art museums in the world - Prado, Thyssen, Reina Sofia. If you want to use your time to see paintings, you will want 2 full days here, then the fast train to Barcelona. You could fly to Madrid, but skip it and spend 2 nights in Toledo. You get to/from Toledo by commuter train (1/2 hour ride) from Madrid. 1 full day is enough to see a lot of Toledo. Depending on timing, you could spend 2 nights, arriving in the evening and leaving in the morning.

Granada will take too long to get to/from. You'll have to skip it.

You can fly from Lisbon to Sevilla; Cordoba is less than a hour's train ride from there. But you'll need 2-4 hours more to Barcelona than from Madrid or Toledo.