Spain in October - Which Cities in which order?

Sine the trip is not scheduled till Oct, I assume the tickets are not purchased. Therefore, the first recommendation is an open jaw ticket so that you are not back tracking to go home. Could be Barcelona and Madrid or into Barcelona, on to Madrid, Toledo, Cordoba, Seville, Granada, and home from Malaga. Or any other combination.

That makes perfect sense, BUT.... After many years of traveling to and fro we are lucky enough to have frequent flier miles to cover this trip. So, for better or worse, the tickets are already booked; open-jaw is not permitted so Madrid is fixed at both ends. That does have the advantage of splitting out time in the 'big city'.

Assuming you'll be jet-lagged the first day...I would suggest 5 nights in Madrid (including your arrival day), four in Barcelona, one each in Nerja, Granada, Ronda, and Arcos, two in Sevilla, one in Cordoba, then back to Malaga for a night before taking the train back to Madrid. One night there again before you go home. That way, you're doing a large circle, rather than backing and forthing to Madrid all the time.
For Madrid-Barcelona and Malaga-Madrid, you can book AVE tickets up to 62 days in advance for as much as 60% off the regular price (which will run you 110-140 Euro pp.) Backtime your travel dates and visit in the early evening of the 63rd day, since the new prices start going in around midnight Spain time...the late afternoon before, for you in Bellevue. www.renfe.es
For Barcelona-Malaga, fly. Vueling does that run from 60 Euro pp....and their tickets for October are available now. Book early to get the best price.
For your car rental, look at picking up and returning to Malaga airport, where you'll get the cheapest rental rates in all of Spain, usually with all CDW and LDW included. We use carjet.co.uk for our rentals. When you come back to Malaga airport, you can take the local "cercanias" commuter train to downtown Malaga for a couple of Euro. Old Malaga is a wonderful place to explore, but you may want to keep the car to get up to the Gibralfaro (the old Roman site where the Moors built a fort, now a parador,) overlooking the city. The Alcazaba and the old section of the city lower down are very nice, and there are some great restaurants and tapas bars in the area. Also the Picasso museum.
Some other stops to consider along the way...two in the Ronda area. Zahara de la Sierra, a magnificent white village clinging to the top of a mountain, and Ubrique, the leather-working capital of Spain. And if you do make it as far as Cordoba, swing by Consuegra, the location of several old windmills overlooking the plains of La Mancha.(cont)

(cont)
Among the hotels you might want to consider, the Best Western Hotel Cervantes...where the rooms are built around two courtyards in the heart of Sevilla. Driving there isn't for the faint of heart though...it's tough to find, the streets are VERY narrow, and there are only about 6 parking spots available, under the hotel and accessible only by car elevator. But it sure is a nice place to stay!
Across Spain, you can also look for "hostals," a class of two-star hotel, usually family-run, that provides very good value for money. For a more modern bent, the worldwide Accor chain has hotel chains running from budget to luxurious across Spain

Norm has a great idea, note the spelling of hostals --- it's not what it sounds like. Also venere.com works real well for hotels in Spain. We find that if you stay above their user rating of 8.0 you can't go wrong. Another good chain is Eurostars, they have a wide range of prices, and sometimes you can get a really good deal is a spiffy place. Previous ideas of routing and day allocation look good.

I was surprised that your frequently flyer program did not allow open jaws. I thought they all did. That is too bad because open jaws generally is a great option all the time.

Phil - Sounds like a wonderful trip. You could start out for a couple of days in Madrid and then take the train to Barcelona. Spend a few days in Barcelona (we loved Montserrat!) and then fly to Granada. My suggestion is a minimum of 2 nights in Granada. From there you could pick up a car as Granada is easy to get out of and head over toward Sevilla stopping in Ronda, Arcos, etc... I would spend at least 1 night in each. Once you reach Sevilla, you could drop off the car and spend 3 nights there. Cordoba could be a stop (not sure if they still have lockers at the bus station across from the train station) on the way back to Madrid. Then, I would spend a couple more days in Madrid with side trips to Toledo and even Segovia if you have time.

We did a similar trip a couple of years ago in about the same time frame, but we started in Barcelona and ended in Madrid. For car rental we used Carjet with no problems - they were great. We only needed the car for 2 days, but it was cheaper to rent for 3. The flight from Barcelona to Granada was on Vueling - we had a little delay but it didn't impact our plans. In Ronda we stayed at the Parador which was wonderful. In Granada we stayed at the Room Mate Migueletes and it was great as well.

You still have time to plan, so take your time and plan what you want to do in each area so you allow enough time to see everything as well as enjoy yourselves.

Again, thank you all - it is so helpful and makes planning not only better but also fun from the vicarious sharing of (and benefit from) your expertise and experiences.

As for open jaw, it is Alaska Airlines from Seattle and then connecting to American but using partner miles. We were told no open jaw. You are all correct on the desirability of open jaw so I can recheck directly with American

Keep it coming!

If you were told "no open jaw" then you were probably lied to. But don't feel bad, that's how the frequent flyer game is played - they do their best to keep you in the dark, and it's your responsibility to know when they are feeding you a line of BS. Nothing new, happens constantly.

It is very unlikely that you do not have options for open jaw flights, but they are not going to do anything to help you figure out how to get them. It may be that either you or they were just not careful with your words ("sorry, no open jaw flights, but you could fly into one city and fly out of another"), or maybe it was just said (or interpreted) that way out of ignorance.

In any case, it's probably not too late to correct the mistake. You will have to pay a bit to make a change, but that's how they want it to go. Even though it will cost you to make the change, it may be (and probably is) worth doing, when you consider that it can effectively extend your trip another day or more, provide you more flexibility in your itinerary - and even save you money.