Spain 14 day itinerary help!!

I flew into Madrid and out of Barcelona two years ago. 1. We spent two nights in Toledo at the beginning of our trip and were enchanted with it. We skipped El Escorial; I was there many years ago as a teenager and didn't feel compelled to make the trip again, but then you need to consider your interests. 2 and 3. We had a little more than two weeks (without a car) and did go by AVE, the fast train, to Sevilla for a couple nights and then by bus to Granada for a night: both convenient and worthwhile additions to the trip. After much deliberation, we decided to fly to Barcelona from Granada and were very happy we did; a short hop by plane beats many long hours on the train. It's easy to get to the Granada airport and from the Barcelona airport by public bus, and you save SO much time. There's a late afternoon flight that arrives early evening in Barcelona. You can comfortably visit the Alhambra one morning and stroll the Ramblas the next morning! If you go to the Alhambra, buy your tickets in advance.
4. We went to Montserrat; it's an easy day trip and recommended if the visit to the mountain and monastery interest you. Otherwise, there is so much to see and do in Barcelona, we stayed in the city.

With 14 days, you have plenty of time for 3 in Madrid, 1 in Toledo, 2 in Sevilla, 2 in Grenada and 3 in Barcelona. That leaves a few extra for other places or longer stays. Don't skip Sevilla or Granada (La-Alhambra) - they are highlights of Spain. Sevilla offers amazing architecture and history and flamenco. La Alhambra is one of the most popular tourist attractions in Europe for good reason. As others have noted, fly from Granada to Barcelona. That is the only long journey - the others are within 2-4 hours by AVE or bus.

check out montserrat in barcelona - it's a good day trip. RS book has the deails on the train ride. you can google about it. yes el escorial is very cool you want to bus from madrid, and then on the way back stop by valley of fallen. a trip to spain without seville/granada is like you didn't go. you have to take the fast train to seville with stop at cordoba. from seville you can take bus or train to granada. there is a night train from granada to barcelona if that saves you a night.

I would stay overnight in Toledo. A fascinating city, filled with history. Take an early AVE train from the Atocha Station in Madrid, in 25 minutes. Get a taxi to you hostal or hotel (Hostal Posada de Manolo is excellent as to location and accommodations) and walk all over the city. The cathedral (with handheld audio guide) Plaza Zodocover, St. Tome, and the various other attractions will be excellent. Also, overnight at least in Sevilla. Really Discover Sevilla Tours is excellent - smaller groups than the larger tours. They can get you Flamenco tickets as well. Patio de Santa Cruz in the old jewish quarter will be a great place to stay. I would suggest Salamanca rather than El Escorial..same train line from Charmatin, just a bit longer. More to see. Over night as well. All of the above are reachable via train. Get your tickets on line at the RENFE site up to 62 1/2 days prior to departure for best prices. The train from Sevilla to Madrid is 2 1/2 hours, and Madrid to Barcelona will be about 3 hours. Plane might be faster and not that much more. Not sure.

Many thanks to each of you for your excellent suggestions and advice - I sincerely appreciate it (and have decided I will fly from Granada to Barcelona... air fares VERY reasonable!). Kind Regards!