My husband and I are travelling to Spain from Nov 8 to Nov 28 and have put together the following itinerary (after researching in guidebooks, renfe.com, movelia.es etc.). Nov 9 - Land in Madrid at 10:30. See Madrid Nov 10 - See Madrid. afternoon train to Toledo. Nov 11 - See Toledo. Stay in Toledo. Nov 12 - Back to Madrid in the morning. Overnight to Barcelona Nov 13, 14, 15 - See Barcelona Nov 15 - Overnight train to Granada. Nov 16, 17 - See Granada. Nov 18 - Train from Granada to Ronda. Trains at 7:00, 13:45, 17:25. 3-hr journey. Nov 19 - See and sleep in Ronda Nov 20 - Bus from Ronda to Arcos. Only 2 buses (9:30 and 15:45) Nov 21 - Bus from Arcos to Cadiz to Tarifa. Many buses exist. Nov 22 - Day trip to Tangier. Back to Tarifa. Nov 23 - Bus to Seville from Tarifa Nov 24, 25 - Sight see Seville Nov 26 - Morning train to Cordoba. See Mesquita, Jewish quarter. Stay in Cordoba. Nov 27 - To Madrid.
Nov 28 - Fly back The part I am a bit concerned about is around the white hill towns and Tangier. While it seems theoretically doable, I'd love to hear feedback from folks who have traveled in these parts if it is going to work out practically. We are not planning to rent a car. Feedback? Thanks!
It's too bad that you are planning three days for Barcelona and only one for Madrid! Trust me, you won't "see Madrid" on your arrival day. I arrived at 8:30 in the morning, and by the time I collected my bag and got out of the airport and into town it was past 11:00. For you, that makes it early afternoon. Then you have to locate your hotel, check in, etc.
I would try to get immediately to Toledo and tack on an extra day in Madrid in the end.
I too would try and get at least one more day in Madrid. I've been there 4 times in the last several years and still haven't scratched the surface. Not sure you need two days in Granada. It was the one place in Spain I wasn't overly impressed with. Other than the Alhambra, I found there wasn't much to do.
Pretty good itinerary overall. There is no overnight train to Barcelona from Madrid. It's a 2.5 hour AVE train ride. You could go in the evening to maximize your time in Madrid. You might adjust the timing of Toledo/Madrid. Maybe go to Toledo first thing off the plane, then spend a couple days in Madrid before Barcelona. Might make things easier, like what to do with your luggage on Nov 12 during the day. There are many cheap flights from Barcelona to Granada. You might consider that over the night train. Most people don't sleep well on them and you lose part of the next day just recovering from lack of sleep. You need one full day (2 nights) in Grenada to see Alhambra and the city properly. Some people like the city and spend another day (3 nights); I'm of crown that once you see the basics, there isn't much more... There should be many more bus options from Granada to Ronda. Cost and time should be the same. Those are the only things I'd change/reconsider. The weather should still be pretty good then and crowds will be very thin.
I would cut back on the number of places you visit. I loved spending 3 days in Granada and 3 in Seville but I'd skip at least some of Tangier, Ronda, Arcos, Cadiz, and Tarifa. Seems to me you'll be spending too much time in transit, checking your watch to make sure you make the train or bus, and checking in and out of your pension/hostal/hotel.
Madrid deserves more time. We spent an entire day just at the Prado. But we are huge fans of art. Even still, there is so much to see and do in Madrid, adding day at the beginning would let you get your bearings there before heading off to Toledo. You do not need an overnight to Barcelona, it's a 3 hour train at the most. Seville is the best. One of my favorites in Europe. Lovely lovely town. Have fun!