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Help! Critique/Reality Chk on Itinerary for Madrid/South Spain/car vs train

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Ok, after reading Rick Steves, Fodor's, and all the wonderful info here, I sort of figured out a rough itinerary and finally purchased tickets! So much more to I need to figure out how long to stay in each to get hotels - crossing fingers tightly

While we have been wanting to go to Spain for quite some time now, due to different factors, it has not happened. We finally have a chance to do that now, however, with short notice to plan. We decided that for this trip, we will just concentrate on Madrid and Southern Spain(Andalusia) with Ronda and Caceres area if possible.

I am now in a bit of a panic because we will be running into Holy Week and Easter which I read could be pretty hectic for this region, specially in Sevilla.

A little about us, if that helps : )

We are a family of three, our daughter is 10 1/2 and is a fun travel companion - she can out-walk me and my husband and do museums, cathedrals, restaurants, etc. very well. While we hope to be able to hit most of the major sights in each town, we also hope to be able to soak up local color and culture in the proccess without having a maniacal pace. We like stopping between sightseeing to poke into spots/shops, or for a little coffee or pastry(or bocadillo) along the way. We enjoy museums but because it could be a long day, we're happy to hit just the highlights, cafe/eating, visiting cultural and historical places,eating, cathedrals, eating, cafes, etc(and maybe a little shopping for me-flea markets, or even department stores/chain stores that cannot be found in US, but just to browse quickly and see what those local places look like), oh and did I mention eating : ) - always small portions, so tapas-land is really perfect for us : )

The longer view for deciding on this itinerary was because there are also a lot of places in the north, including Barcelona that we also want to visit someday, we decided to for now, just concentrate on Madrid and the southern part, and then on another trip, do Barcelona and the major sights up north. I know from reading here that it will take so many trips, and time, to fully explore all that Spain has to offer, as many of you have. For now, we want to hit at least these highlights.

So far, this is what I have down. I know that this is probably too much, but with wishful thinking, maybe not? if it could be included with our time frame, that would be great! If not, please feel free to say "skip" or "yes you have time, "this is how I would break this up", and "on the way to this, you can also add this to your list" : , or "instead of this town, go here instead" :)

We will be arriving in Madrid from a red eye, early in the morning on March 30th, and leave on April 15th. So we really only have 16 days/nights. I tried to get a multi-city ticket so we could fly out from Sevilla/Granada or Malaga back to the US but the ticket prices I got was too exorbitant and with very long layovers in other parts of Europe that as much as I didn't want to retrace back to Madrid, in the end, it was worth it anyway. Besides, I thought, we could just stay a couple of nights there before heading back to sort of just decompress(to the extent that one could : ) before heading back to Boston.

This was the order I was thinking but we could also turn the order around(Madrid, Granada, Ronda, Sevilla, etc.)

Madrid - daytrips to El Escorial, Segovia-total number of days?-6 nights total(need to break into two parts-beginning and end of trip)

Do day trip to Toledo, or stay in Toledo for 1 night and if we do end up staying one night here, pick up the car here and start the drive from here to(wither Caceres or Granada, depending on the order you folks suggest)

Caceres-1 night, drive through and quick stop to Merida and Zafra on the way to Sevilla
Sevilla-4 nights, day trip to Cordoba
Ronda-2 nights(include Cueva Pileta- I read this somewhere)
Granada-3 nights

I could also change the order around. I was trying to avoid being in Sevilla around the semana santa because I thought that it would be impossible to get hotels but when I just looked, there are actually still some available - probably not the most ideal hotels but at least we still would have a place to stay.

And if we decide to do Granada as our first stop from Madrid, and work our way through the other way around, does anyone have any suggestions for a town in between Granada and Madrid just to break up the drive maybe for lunch before continuing on?

While it would be nice to see some of the festivities, I was wondering if it would just be best to avoid it at that time because it would be too intense and crazy busy, so instead, head down to Granada first and loop around the other way and be in Sevilla on the second week.

And lastly, I know that the trains and buses are very efficient and fast. However, when I priced them out for each leg of the itinerary, on renfe, because there are three of us and we are doing this on such short notice, we cannot get discounted tickets and the car rental is so much cheaper, even if I factor in parking fees. Am I just imagining things?

Is there a website where I can still get discounted fares?

I know that the car will virtually be unusable when we are in historic centers and would hate to be paying for rental and parking on days that we won't be using them but it still seems to come out cheaper. (Unless of course I am able to get discounted train fares). Plus, with a car, there is the added flexibility of being able to stop in little towns along the way to our next home base. BUT, I keep reading people saying, that even if the car is cheaper, it's not advisable - am I missing something?

THANK YOU, THANK YOU!!! And apologies for long post! I was thinking if I should have broken this up to separate posts but thought it might be helpful to know the entire context.

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