Itinerary help for Madrid to Southern Spain

There's no way I'd spend the last night in Toledo. Barajas is not far from downtown Madrid, so you have the option of staying in town rather than at the airport if you don't mind the cab fare. There's also bus service from near Atocha Station and train service--lots of options if you're not too concerned about arriving at the airport on time or are willing to get up a bit earlier.

I love Toledo and hope you can find time to spend two nights there.

For a stopover in Cordoba you'll need two separate train tickets (Madrid-Cordoba and Cordoba-Seville).

Almagro is interesting and has a somewhat different look from the other places you plan to visit, but unless you need it as a meal stop, I'd urge you to be sure you have time for Toledo before spending time in Almagro. Toledo is absolutely one of the top sights in Spain; Almagro is nowhere near that. I'd leave Granada and drive straight to Toledo for two nights.

You'll get lots of itinerary advice on this, here is mine!
Upon arrival in Madrid, head straight to Cordoba (2 nights)
Train to Sevilla (3 nights) pick up rental car on last morning
Drive to Ronda, with a stop for lunch in Arcos (2 nights)
Drive to Granada, drop off car (3 nights)
Train to Toledo, via Madrid (2 nights) - you have to go through Madrid to get to Toledo
Train to Madrid (4 nights) One on of the Madrid days, day trip to Segovia

We found Arcos to be an interesting stop, but glad we didn't spend the night. Driving is easy, the roads are well signed and safe.

You could gain a couple extra nights for one more stop by giving Granada 2 nights rather than 3 and Madrid 3 nights rather than 4. If you do this, you could feasibly add in another city - possibly Jerez.

I think it's not the best plan to stay in Toledo the night before your flight.
Happy travels!

Thanks Kathleen. I'll have to give some thought to that. I see logic of ending in Madrid, but will make for a really long trip...already 15 hours of travel there....and 1) hubby actually likes driving and wants to explore more than train and 2) as planned I have a splurge hotel in Granada on his birthday.

If I swapped it all around could maybe make birthday in Toledo instead. Granada vs. Toledo for a splurge?

If go straight to Cordoba what do you do? Take taxi to Atocha station and train from there?

" Is it crazy to get up early, drive to Madrid, return car, and make airport by 7:30 AM? Is it possible to return car before and take car service, bus, train from Toledo directly to Madrid Airport early in the morning?"

I wouldn't do either of these. Car rental return can take a lot longer in Europe than in the US - what if you're held up? And there is no direct service (no "one seat ride") from Toledo to Madrid airport by bus or train - you have to go through Madrid and change, unless you can arrange a prebooked cab (likely very expensive).

A taxi from central Madrid to the airport (in either direction) has a fixed rate of €30, and there is no need to tip beyond this. To make an early plane, I'd probably just take a taxi.

I like Kathleen's itinerary a lot; it avoids backtracking, and puts you in Madrid at the end. The train from Granada to Toledo is the only "long" or "difficult" ride.

Toledo to Madrid Atocha is a spur line on the train; you always have to change to get anywhere else from Madrid. I learned that when searching for these connections, the Renfe website doesn't show them all, for unclear reasons. When I went from Toledo to Barcelona, Renfe only showed two train connections all day, while the Bahn website showed many. I ended up having to book it as two separate tickets to get the times I needed.

I was cross-posting with you.

"If go straight to Cordoba what do you do? Take taxi to Atocha station and train from there?"

You can do this. But your ticket from Madrid Atocha to Cordoba includes one ride on the Cercanias, and you can use this "free ticket" to take the Cercanias from the airport (Terminal 4) to Atocha. If you're not arriving at Terminal 4, a taxi is certainly easier than changing terminals, but then you'd have to buy your train ticket at Atocha; I presume (but don't know for sure) that the ticket lines at the airport station are shorter.

Toledo (2N)
Cordoba (2N)
Sevilla (3N)
Arcos (1N)
Ronda (2N)
Granada (2N)
Madrid (4N)