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Spain trip

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I am lost. I have a trip for 12 days / 13 nights I am flying in to Madrid early morning. I want to immediately take the train to Seville to start my holiday. want to take a side trip to Cordoba and I want to visit caves in Ronda and then maybe travel to Granada.
After that I want to get to Barcelona the quickest way, I'm thinking late night plane. We are meeting friends and going to a football match. I want to go on a side trip to Montserrat. Then train from Barcelona back to Madrid to see the sites there and also Toledo.
My trip is in 6 weeks (September). I have not booked anything but the international flight
Not at all sure about the trains or planes.
I am 50ish so I am not about to back pack it. Too much luggage.
How do i make this work. Should I buy train tickets when I arrive or beforehand. Then when I arrive at the train stations are there taxi's readily available to get to the hotels?
Anybody have suggestions for hotels or tours or things to see.
All suggestions gladly accepted!!

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