Best way to spend nine days in Spain

These are wonderful day trips from Madrid: Toledo, Segovia, Cuenca
Barcelona: a few days on the Costa Brava, a day trip to Montserrat

What time of year is your trip?

I loved Toledo, which is totally different from Madrid. You'd have numerous opportunities to see Mudejar architecture there, especially nice since you won't have time for Andalucia on this trip. Toledo is much quicker to reach from Madrid than Salamanca is. Actually, I think transportation is also faster to Segovia and Cuenca. Those are all interesting destinations and can be done as day-trips, avoiding the hassle of changing hotels, though I spent at least two nights in each of them (on a much longer trip). Toledo can be a spur-of-the-moment decision (assuming you don't have time to spend the night), because Madrid-Toledo rail fares do not increase as your travel date approaches. You'll save money by buying a round-trip ticket, though. (Always check that possibility in Spain.) For Segovia fares will be somewhat higher for late puchases, and for Cuenca, the AVE fare can be painfully high if you don't buy well in advance.

Zaragoza has some Mudejar buildings, but not as many as Toledo, which I think is one of Spain's very top destinations. I haven't been to Valencia.

I also haven't been to Montserrat yet, but I wonder whether that could be the hiking opportunity you're looking for. It's a common day-trip from Barcelona

What a great reply! We're going at the end of March (thanks for reminding me; I updated the original post). Toledo sounds like the place to go. I'll definitely look into all the places you mention.

Most folks on the forum recommend flying between Granada and Barcelona because it's faster than the train, even taking into account lead time at the airport and extra time to/from airports to city centers. You will love the Alhambra. 2 nights in Granada is sufficient - one day at the Alhambra and a few hours to see the other highlights. You won't find Moorish or Mudejar in Madrid. But you will in Toledo, Cordoba and Sevilla. If you are flying into Madrid in the morning or even early afternoon, you could go straight to Toledo or Cordoba.

The benefits and disadvantages to going to Toledo . . . It's a a spur line of the railroad, the only way there and back is the train, which is fast and cheap. You need to allow at the very least 15 minutes to change trains in Madrid, it's a big station and the Toledo trains are somewhat remote. Good on arrival because of the cheap tickets, long trip to Granada though - at least 5 hours, maybe more depending on the connection in Madrid.

The benefits and disadvantages to going to Cordoba . . . It has the unique Mezquita, it's a 2-2.45 hour train trip to Granada, you can day-trip to Sevilla. But train tickets are more expensive if you need to buy at full fare (on the spot). Early purchase is about €44 each, full fare €63.

this article about Renfe/trains explains everything you need to know.

Thanks for the response. I'm really heartbroken about missing the Alhambra, but travel the time for all these places seems to be too much. Even flying would take nearly an entire day with getting to and from the airport, waiting around there, checking in and out of hotels... I'm really torn now between Madrid->Seville->Granada->Barcelona or Madid with a trip to Toldeo->Barcelona with a trip to Montserrat. I don't want to spend half of our time on trains and in airports.

Reconsider flying from Granada to Barcelona. Granada's airport is small, chances are you won't need more than an hour or so at the airport. Then it's an hour or less from the airport to the center of Barcelona . . . 1/2 day

Will this be your first trip to Spain? Do your 9 days include arrival and departure days? If yes to both, consider the following itinerary:
Day 1 - arrive Madrid, take train to Toledo, spend the night.
Day 2 - enjoy Toledo, take late afternoon train back to Madrid, spend the night.
Day 3 - enjoy Madrid - El Prado, Parque Retiro, Mercado de San Miguel, Palacio Real, etc.
Day 4 - train to Granada, spend the night.
Day 5 - enjoy Granada - the Alhambra (book tickets by this fall for best results).
Day 6 - Granada morning flight to Barcelona. The flight experience from check-in to arrival in central Barcelona (Plaça Catalunya if by metro or Aerobús - only 30 minutes) won't be too long nor tiring. Enjoy afternoon and evening in Barcelona.
Day 7 - Barcelona - sights too numerous to mention here
Day 8 - Barcelona
Day 9 - fly home.
There is so much to see and do in Barcelona, I would not bother with a day trip from there unless Day 9 is not your departure day or you have already been to Barcelona before this trip.

Thanks everyone! Yes, this will be my first trip to Spain (and possibly my last!) and no, the nine days are not counting my departure and arrival. After hearing from all of you and looking into it a little more, I'm less worried about the flight time. I'm now leaning towards two days in Madrid, two days in Seville, one in Granada, and four (three and a half discounting the flight) in Barcelona. Should I scrap Seville and go to Toledo instead? I've heard Seville is a very unique and charming city and that it's the place to be for flamenco shows, which I would love to see.

With 10 nights (9 full days) ... and to ‘see it all’.

Day
1. Arrive Madrid (3 nts)
2. Madrid
3. Day to Toledo
4. Train to Sevilla (2 nts)
5. Sevilla
6. Train via stop in Cordoba (for Mezquita) to Granada (2 nts)
7. Visit the Alhambra
8. Fly to Barcelona (3 nts)
9. Barcelona
10. Barcelona
11. Depart Barcelona

While I would love to see all those cities, I worry that would just be too much rushing around and sitting on trains and not enough enjoying the places and relaxing.