Itinerary 14 days in Spain

A good start would be to stop telling yourself that you have 14 days in Spain. You have 12. :)

Here’s some thoughts:

Day 1: Fly to Barcelona (lose one day); Day 2: Arrive; Day 3 - 5: Barcelona.
Day 6 - 8: Fly to Granada (or train); Granada
Day 9: Ronda
Day 10: Train to Madrid, but stop for a long lunch at Córdoba & see the Mesquita.
Day 11 - 13: Madrid & take a day-trip to Toledo on Day 12.
Day 14: Return to USA

Personally, I liked Madrid, but I loved the smaller towns in southern Spain, so I would do this:

Day 1: Fly to Barcelona (lose one day); Day 2: Arrive; Day 3 - 5: Barcelona.
Day 6 - 8: Fly to Granada.
Day 9-10: Ronda
Day 11: Córdoba
Day 12-13: Madrid w/ possible day-trip to Toledo
Day 14: Return to USA

I count that as 11 days, because so many people are zombified (sleep-deprived and jetlagged) after an overnight flight.

I'm assuming you plan to use public transportation.

I have no issue with the places you're going or--given the limited time you have available--the number of days spent in each place. I suspect, though, that the order may be non-optimal. You cannot get from Toledo to Granada without traveling back through Madrid. Toledo is on a spur railway line that connects only to the capital. Much as I dislike mid-trip flights and like the idea of sleeping in Toledo, I'd investigate flying from Barcelona to Granada, then traveling to Madrid, treating Toledo as a side-trip.

Better would be to reverse the trip, flying into Madrid and going immediately to Toledo on your arrival day. (Oops: Skipped over Madrid here. First back to Madrid.) Then Granada by train/bus and fly to Barcelona. That would allow you to spend a couple of nights in Toledo.

I like Ronda but don't think I'd choose it over Seville or Cordoba. Your trip, though. Not sure what that would do your logistics, however. I've never looked at train/bus schedules between Ronda and Granada or Madrid.

Here's the Deutsche Bahn website, which I find most user-friendly for schedules.

And here's Renfe for fares.