First, you can leave your bags in the car as long as they are in the trunk, and not on the seats. (Probably nothing would happen, but why risking? Have them there when you park, and don’t be obvious, don’t leave sunglasses, etc in plain view. It is a general precaution.
I know San Sebastian, and it won’t dissapoint you.
As you’ll stay in Barcelona, visit the Picasso Museum there, much better than Malaga’s. So you can skip Malaga at all and go straight to Nerja via motorway. Then you must carry on to Motril and then north to Granada. It is a total 2h30min drive , long though beautiful by the sea.
The Ronda part I find ok, though there are several routes from there to Arcos and Seville. We’ll get there further on.
The drive Seville to Toledo is barren, monotonous and boring, I'd recommend the train.

josele,

Thanks for the feedback. I have read a number of your other posts and so I know you are one of the resident experts. Thanks for taking the time.

I have seen several references to you as an artist along with your comment in your previous post. What type of art do you do? Are there any links that show your art.

My website is www.jgonzalezbueno.com. The english part is a bit out of date, but working on it.

From Madrid to Segovia are available non-stop buses but the train is a commuter train that does many stops.

A couple of San Sebastian thoughts:
-It's perhaps my favorlite place in Europe
-There are many terrific pintxo bars outside Parte Viejo. Check Maribel's guides. The food is so good everywhere it is easy to just stay in the older area and not venture out. Try to get out of the "tourist" area at least a bit. [Altho, I never feel that I am in a "tourist" town when in SS.]
-there is a great panorama of the city and bay from the top of Mount Ugelde. You can drive up or take a funicular from the base. Worth an hour.
-If you are going to "splurge" on an expensive meal, SS is the town to do it in. More Michelin starred restaurants per square mile than anywhere else on earth.
-I enjoy some of the smaller coastal villages between SS and Bilbao. Hondarribia is pretty but more urban than the villages to the west. Incidentally you can go to Honarribia on a SS city bus and avoid parking problems.
-I have mixed emotions on Pamplona. It's one of those place you "have to go" but I was not overwhelmed. Beautiful drive tho.
-To get a great feel for the Basque territory, get the book "A Basque History of the World". It's not large, very easy to read, and really tees you up to understand a bit about one of the most fascinating peoples and territories anywhere.
-Fly or drive to BCN? Not a great deal of difference in door to door time. I like to car option as one can poke about the side roads if you want. However, you are then left with the challenge of driving in BCN and getting rid of the car there. In May I flew Bilbao to BCN on Spanair for 37E. Saturday afternoon. Spanairs prices vary widely depending on day and time of day. It's worth you time to check there schedules over several days.
-I have written a fawning description of SS at Marshlands.blogstream.com. It may be of interest.

You have received very good advise, let me add a couple of pratical notes.
I found it much, much cheaper to fly Madrid to Bilbao than to San Sebastian so check that out since it would be hard to be so close and not go to Bilbao. The Guggenheim is awesome in architecture, art is just OK. But the Fine Arts Museum is absolutely first class. Like San Sebastian, the tapas are awesome.
Having a car once in a city is a big nuisance. Parking is always a major problem. You might consider taking the AVE from Seville to Madrid, it's wonderful. You can take a commuter train to Toledo from Madrid, which I have done many times, or a bus, which is highly recommended by several regulars on this site.
Paradores have gotten much more expensive in the last few years, but if you are 60 or more, you can get a very good discount. Go direct to the Paradores web site and book direct, because you can see what special offers fit your needs.
In Madrid we stayed at the Gran Hotel Canarias, and I can't think of a better location for museums, it's in the same circle as the Palace, but the price is reasonable. Check out their web site.
Your trip sounds fabulous, we have been there many times, each area has been special, though we've not been to Costa del Sol.

Weber6560:
Thanks for the recommendations on San Sebastian and for sharing your Marshlands review with us. We look forward to experiencing what you have.

What are your thoughts on: (1) staying in SS for the 4 nights and exploring the Basque/La Rioja regions from there OR (2) move after 2 nights in SS to a more central location in La Rioja area (e.g. Laguardia) for 2 of the nights?

Also, we have decided to drive to Costa Brava rather than fly and stay there for 2 nights before going to Barcelona (and returning our car). Is there a problem I should be aware of in returning a car in Barcelona?

Aleta:
Thank you for your advice as well. We have decided to drop our car off in Seville and use trains for Seville-Madrid-Toledo-Madrid. We are starting to make our hotel reservations so your suggestions are timely. We will check out the Paradores in each of our locations. The Gran Hotel Canarias sounds great. One question about location: is it better to be near the Prado or Plaza Mayor or are they close enough to each other that it does not matter?

I am finding a number of San Sebastian hotels are not available on Sept 20 & 21. I have not heard from the others yet but there could be a problem going those days which would require revamping my plan. Is that the Wine Harvest Festival causing that or is there some other event. Any ideas of accommodations?

I posted a follow-up to this stream at:
http://www.fodors.com/forums_reg/pgM...=0&start=0

The International San Sebastian Film Festival is what causes that in September. It's a huge event, something like Cannes or Venice film festivals.

Kend, Que tal?

Fine, Comfy Finishing planning my trip to London (I'm going on Friday !!) ..too much planning for such a short time, LOL (only 3 full days !!)

Well, better do a long report on those three days when back Make sure to have fun.

Trip report ? You will get too bored... But yes, I'll have some fun for sure