Itinerary Check & Toledo to MAD

I would definitely not spend that last night in Toledo. For a 10:40 AM flight you need to be at Barajas by 7:40--and your airline may have even more conservative advice; you need to check that. Some airlines are recommending 4 hours at some airports.

I checked the train schedule for a Tuesday in early May and found the first departure from Toledo is at 6:25 AM, arriving at Atocha Station at 6:58. In theory you could get to the airport by 7:40 (there are buses, local trains, the Metro and taxis--lots of choices). But what if there's an issue with that first train out of Toledo? I wouldn't risk it with a transatlantic flight on the line.

i think you've done the best you can with 9 nights. There's no room for Ronda. You're short on time in Seville as it is.

A complicating factor is that to go to Toledo, you must transit back through Madrid (it's not terribly onerous, but kind of a time suck). For that reason, I would consider saving Toledo for a future trip. You could add a night to Sevilla, or add Ronda if you prefer (I would note sacrifice time in Cordoba though).
I agree you should be in Madrid the night before your flight.
I'm just wondering, have you checked all variations of the order of this plan? For example, we flew into Madrid and headed to Cordoba first since the train distance was shortest. You could play around with the order to see if anything looks better--for example, if you went to Cordoba last, perhaps you could make it to Madrid the morning before your flight (not something I would risk, but I am particularly terrible at "morning").

I have gone from Barajas to the middle of Madrid by taxi a few times, and I remember nothing notable about the cost.

We always stay in Madrid our last night and take the metro to the airport. The metro operates beginning at 6am. From the Puerta del Sol to the airport will take about 45 minutes. There are other ways to get to the airport. There’s no way I’d spend my last night in Toledo as too many things could go wrong trying to get to the airport.

Another possibility would be stay in Alcalá de Henares if there’s a train that can get you to the airport in time. Alcalá de Henares is 15 miles from the airport so you could even take a taxi if need be.

Cordoba was a good thought; its position is such that it fits into the itinerary in several places. But it doesn't help us out here. The first train from Cordoba doesn't get to Madrid until 9:10 AM.

We’ve done private transfers from Barajas to Toledo a few times via Suntransfers (suntransfers.com), but never in the other direction. You could check online to get a quote for your particular needs. I have found them to be reliable and reasonably economical, but I’m usually traveling with 5 or more people.

Thanks for the great feedback all! Seems like we should def stay in Madrid the last night. And we won't change anything with the Cordoba section to try to fit something in. (just need to return to see Ronda!)

But I've read so much about staying the night in Toledo. Should we do our last two nights Toledo then Madrid? Or would you recommend staying in Madrid both nights and doing Toledo on a day trip? Unfortunate but with our time allowed I'm grateful for all we're squeezing in.

(I really appreciate the train tix help; renfe is not my fav international train site to navigate!)

Again, many thanks!

That's a tough call. I would not add a one-night stay or a day trip, but I just like longer stays and am more likely to miss a place than to squeeze one in. You might look at the logistics of going to Toledo first, spending a night, then going to Cordoba (via Madrid)--perhaps that limits the train time a bit.

Ok I will look at the train schedules thoroughly. Thanks again for the help!

I love Granada but I wouldn’t travel to the other side of the country to see it this trip. Sevilla is beautiful and Cordoba is an easy day trip by train. I would just stay in Seville. Less packing and unpacking. Loved Toledo and it’s great to be there at night. I wasn’t excited about Ronda.

What about putting Toledo at the front of your trip and then flying from Seville to Madrid the night before and stay close to MAD?

I personally would not omit Granada from this trip. I can't imagine going to Andalusia and missing Granada and the Alhambra. The Alhambra is one of the most beautiful and amazing places I have seen. And it is not at the other end of the country. It is in Andalusia, and it's very easy to get to via train from Cordoba.

It wouldn't make sense to fly from Seville to Madrid. A train will whisk you between the two cities in 2-1/2 to 3 hours, city center to city center.

take train from Toledo to Madrid-Atocha station (AVANT train) and then take Uber (20 minutes and $20 if non-peak times, cost can be 2X during peak times) to airport. no need to stayover in Madrid.

madrid airport is large but was efficient. if your flight departs at 10:40, bag check etc around 9 am > transfer from Madrid-Atocha to airport from 8 to 9 am therefore arrive in Madrid-Atocha by 8 am. please plan accordingly. train from Toledo to madrid-atocha is direct and on time. so the 6:25 AM, arriving at Atocha Station at 6:58, mentioned above by acraven is a good one.

Note there are in fact direct trains from Atocha station to Barajas airport, the Cercanías trains in Madrid (i.e. the regional/commuter rail system) -- specifically, lines C-1 and C-10 will take you there. The trip is 29 minutes and they run every 13-15 minutes. If you are arriving by rail from Toledo then presumably you are able to handle your baggage on public transport, so it shouldn't be too difficult to make the transfer.

That said, I'd echo those who have advised to stay in Madrid the night before, for peace of mind. Toledo is close enough to the airport (~90km) that should you need to scramble to get a plan B to the airport the morning of, you'll likely be fine, but that's not to say it wouldn't be a stressful situation.

It depends, I suppose, on how one defines "most important". In a city with ten fabulous sights, one could say the top two are the "most important"--though people might well differ on what they consider the top two. But what about the other eight? To try to cram Seville into one day is as shortsighted as traveling to my city (Washington DC) for just one day. Crazier, really, because for an American Seville has the attraction of an overall feeling of being different from home in a way that Washington DC does not.

Sevilla 3N
Cordoba 2N
Granada 2N
Toledo 1N
Madrid 1N

Instead, start in Toledo, so you have a short distance to travel and a cheap train ride - since you don't want to book in advance with the uncertainty of arrival times. Perhaps 2N, then an early train to Madrid and transfer to Granada 2N. Then Sevilla, Cordoba, Madrid. The train from Sevilla to Cordoba is less than an hour, so you can choose to spend a whole day sightseeing in Sevilla, then go to Cordoba for dinner and sleep, or leave Sevilla early and have almost the whole day to spend in Cordoba. Thus either 3N/1N or 2N each. BTW there's luggage storage in Cordoba at the bus station across the street from the train station, so you could leave your luggage there and just take a small overnight bag.

Chani, I love the suggestion of doing Toledo first to make train tickets less challenging! Thank you!

Doing basically the same thing in late May ... arrive Madrid in the early AM and look around ... Toledo the next day, back to Madrid ... on to Granada for 2 days, then Seville for 2 days, then 1 day in Cordoba, back to Madrid for a day then home ... trains between all cities, dang that Renfe site is difficult.