Which two cities ?

The easiest by far would be Toledo.

Yes, Toledo is the closest and different. Cordoba would be my second choice. The mezquita there is so beautiful, as are all the Mezquita, Alcazar, and Cathedrals in Spain.

One-way travel times by train from Madrid's Puerta de Atocha station:

Toledo: 31 - 33 minutes
Segovia: 25 - 27 minutes
Cordoba: 1 hr. 42 min. and up
Seville: 2 hr. 23 min.
Granada: 3 hr. 19 min. and up

All those cities are fabulous and worth more than a day-trip, but the obvious choices are Toledo and Segovia. Not only will you waste less time sitting on trains, the tickets will be a lot cheaper. Although tickets to Toledo do not increase in price if bought at the last minute, those trains (and the trains back to Madrid) do sometimes sell out, so it would be smart to get them before the day you plan to make the trip.

Spending so much time traveling to the last three would leave you with seriously inadequate time for sightseeing. Cordoba, Seville and Granada will fit together well on a future trip to Spain.

I agree that the two would be Toledo and Segovia. We did stay overnight in Toledo as there is a lot to do. I day tripped to Segovia and felt it was a perfect day trip from Madrid. At the time I went (about 5 years ago??) I took a train to Segovia and then there was a bus that seemed timed to the train arrival. The bus to the aqueduct may have been about 10 minutes.

For Toledo, the train station is gorgeous, BTW. We took a taxi from the station to the old town. Its too far to walk and its uphill. I believe acraven took the bus from Madrid which, I think, has the advantage of dropping off by an escalator up to the old town.

I did take the bus from Madrid to Toledo, and it gets you closer to the escalators, but the train is a lot faster, so I'd recommend that to anyone without an excess of time--and certainly to anyone day-tripping to Toledo.

I recall a much earlier post from someone who recommended the little tourist "train" (actually a road vehicle) that makes a loop past several sights. It was pointed out that one of the stops is at an overlook outside of but with a fabulous view of the historic center. I didn't do that, but it sounds like it would be a nice idea, especially for folks into photography. Assuming there's a stop at the train station (which I don't know for sure), that would solve the question of how to get up to the historic town from the train. There is, of course, regular bus service as well.

There is a famous viewpoint of Toledo on the other side of the river from the old town. We were going to take the little train which seemed like a HOHO kind of thing. I thought it was a little pricey, and we didn't have the time to take full advantage of it. My husband who typically leaves all planning and logistics to me suggested checking the taxi price. We ended up paying about 6 euro for a ride out of old town and across the river for beautiful views. It was far cheaper and allowed us to plan the route. I may have said this in a trip report, travelers could grab a taxi from the train station and detour across the river for the viewpoint, prior to going up to the old town (or do it on the way out of town)

That may have been me — my family loves the Zocotren! It is very touristy but a nice way to see Toledo from across the river. It does a loop around the city and outside the walls, but its only stop is at the overlook, so no catching it from the train station. Total ride is about 45 minutes.

You can buy tickets at the kiosk in Plaza Zocodover; get them as soon as you get into Toledo so that you can choose the best tour time for your day; they do sell out as the day goes on.

To get from the train station up in to the city, you can walk (quite an uphill climb), walk around the base of the city (flat walk, maybe 1/2 mile or a little longer) to the escalators and then take those up, or you can grab a couple of taxis from the train station (very cheap).

Have fun!

If you’re picking 2 of the 5, then Segovia and Todelo, definitely.

Hopefully some, if not all of you will be able to travel to Spain again, and have time to visit each of the other cities properly. Each needs more than a quickie day trip, and a vacation in the Andalusia part of Spain could feature all or some of those other 3 cities.

On our last trip, we actually stayed 1 night in Segovia, and did Toledo as a daytrip from Madrid. Enjoy your time in June!

I was hoping someone woukd recommend Seville😁. Knowing its a 2+ hr train ride I was thinking of jumping on the first train out and taking a late train back. It does sound a bit rushed I can see and I'll have to reevaluate. Thanks for the sound advice everyone. Making Seville a stay over rather than a day trip might be the answer.

I agree with the Segovia and Toledo suggestion. Alternatives could be Ávila for a couple hours, then on to Salamanca, or, Alcalá de Henares. Choices, choices.

The escalator (Escalera mecánica del Parque Recaredo) up to the historic center is just past the Bisagra gate and a mile from the train station.

There are six overlooks on the south side of town very near to each other. If one leaves town via the Puente de San Martín the mirador panorámico is 2.6km. From the Ronda de Juanelo bridge it’s only 1.3km. A taxi wouldn’t shouldn’t cost much, or one could take the L71 bus. It runs a route around town from Plaza de Zocodover. The best view is probably from the Parador. The view from the overlooks is the same place El Greco painted his “A View of Toledo.”

Seville is a great destination, but to me it calls for a minimum of 4 nights (3 full days). With Cordoba so nearby, and Granada a third important city in Andalucia you don't have time for, I just can't recommend a too-short visit to Seville when it requires so much transportation time. I'm sure you'd enjoy your limited time in Seville, but you'd need to go back on your next trip anyway, and you wouldn't have seen Toledo or Segovia.

For a short day trip - definitely Toledo.
Also, Seville, the capital of Andalusia. The Alcazar palace, a beautiful example of Mudéjar architecture. The Cathedral of Seville is also a must-see, as it is the largest Gothic cathedral in the world and home to Christopher Columbus' tomb.

I agree with acraven. Sevilla is worth so much more time than a day, or two, trip. One would spend almost as much time in transit as time in the city. If one has never been there before, just visiting the cathedral and Giralda tower could take 3 hours. The Alcázar an equal amount of time.

Just to clarify, in case you decide to head to Toledo from the train station:

There are 2 sets of escalators up to the higher points of the city. One is near the Bisagra gate and another set is from the tourist bus station parking lot.

The ones from the bus parking lot are much closer to the train station — google maps has the walk at 450 meters on level ground. You can find the directions by putting in “Safont escalator Toledo.”

Hope this helps.