Help with travel itinerary!

For a start, see three-week (and lower on the page, two-week) route suggestions at https://www.ricksteves.com/europe/spain/itinerary. That gives you an idea of how to fit it all in, even if your list is slightly different.

Transport connections (travel time and frequency) are summarized of each chapter in Rick's Spain book, or How to Look Up Train Schedules and Routes Online gives you the DB train schedule link and tips for using it.

For seeing as much as you can easily in 2 weeks...
Fly in to Barcelona - 4 nights
Fly to Granada - 2 nights
Train to Ronda - 1 night
Train to Sevilla - 3 or 4 nights (day trip to Córdoba)
Train to Madrid - 3 or 4 nights (day trips to Segovia and Toledo)
Depart from Madrid

Schedule 4 days in Madrid if you plan to be heavy with your museum schedule, otherwise 4 days in Sevilla with a possible visit to Jerez.

How much time you stay in Madrid depends on whether you love painting. If you do, you'll want 2 full days just for the "big 3" (Prado 1, Thyssen/Reina Sofia 1). The Palace is one of the best in Europe. Other than that, there's much more of interest in your other cities.

It's possible to day-trip from Madrid to Toledo, but it's much better to spend 2-3 nights. You will need to take the commuter train from Madrid. You can leave your luggage in storage at the Madrid Atocha train station and go with just a small overnight bag to make it easier. I'd go right to Toledo on arrival. Buy your tickets to Madrid and to Toledo at the airport train station. Allow enough time to navigate Atocha (and check bags if you want to).

It's possible to day-trip from Seville to Cordoba, but it's much better to spend 2-3 nights. Cordoba and Toledo have a quiet aura in the early mornings and the evenings that you won't find elsewhere. And there's lots to see and do in both.

I would rent a car in Seville to drive through the hills to Ronda (2 nights) and drop it off in Granada (2-3 nights). Then bus or train to Madrid. No matter how much time you decide to spend in Madrid, that should be your last stop so you are near the airport.

Thanks so much for your suggestions. We have decided to skip Barcelona on this trip and do it another time combining it with France. I should have pointed out we are more outdoor exploring type travelers who love to wander streets and take in the culture rather than spending hours in a museum. Any further advice would be appreciated! Lori

Without Barcelona included ...

Fly in to Malaga - 2 nights
Bus to Granada - 2 nights
Train to Ronda - 1 night
Train to Sevilla - 3 nights
Train to Córdoba - 2 nights
Train to Madrid - 4 nights (day trips to Segovia and Toledo)
Depart from Madrid

If you like "wandering streets and taking in culture," don't discount Madrid. It's a large and diverse city with a lot of street excitement. Wander the various neighborhoods - La Latina (detailed in Rick's book) is hipster and South Asian, Chueca (not in Rick's book) is gay, and Salamanca (not in Rick's book) is wealthy and groomed. Salamanca's motto should be "Feeling rich and beautiful? Join others who feel the same in Salamanca." If you find the center a bit gritty (many do), Salamanca is a nice respite. And Retiro Park is also very nice.

Even if you're not "into" museums, the Prado really shouldn't be missed. They have one of the largest collections of stunning pieces anywhere. And the Sorolla Museum is in his former house, so it's of interest for more than just the paintings (which I happen to like a lot as well; if you like Renoir, you'll like them too).

Harold, you sound as if you see Madrid through my eyes - we are very much in synch.
Maybe we need to take Chani under our wing(s) for a visit to Madrid.

Thanks so much! We are planning 3-4 nights in Madrid with some possible day trips. Love these ideas!

Ooh, take me, take me . . . I know it's fun to spend time with Harold and I'm pretty sure I'd have lots of fun with David.

Harold does make Madrid sound great, and on my second visit I liked it more than my first, not that I disliked it the first time, but I'd still rather be in Cordoba or Toledo or Barcelona . . . . . haven't started counting the days yet, but takeoff is in about 6 weeks. Sorry, guys, but I'm skipping Madrid this time and exploring Malaga instead.