Madrid-Toledo-Sevilla

I see the pros and cons of doing Toledo as a day trip (vs. overnight - you should definitely go to Toledo one way or the other).

Pros to overnight: Toledo is very busy and heavily touristed during the day. The section near the Cathedral and Zocodover can get downright packed and unpleasant at peak times. The other side, near the El Greco museum and the synagogue is less crowded but still busy. The town is much less crowded at night and you can enjoy the beautiful lighting of the cathedral and streets pretty much all alone. Which brings us to the cons...

Cons to overnight: The flip side of being a hugely popular day trip is that things are very, very quiet at night. Sights close earlier than in other parts of Spain, many restaurants are also closed, and there's no street life to speak of. I don't mean "nightlife" like clubs - that's not my thing - just people out walking and eating and drinking. The paseo and tapas scene you get in most of Spain is absent. Some people consider this peaceful, others consider it dead.

I think I might rather see the sights in Toledo during the day, and then spend the night in Madrid and find a lovely, lively, local bar or restaurant and walk around a fun area. But then again one of my favorite experiences from my last trip was sitting on my Toledo apartment roof deck watching the lighting change on the cathedral as it got darker. So...I'm no help, sorry.

I liked staying several nights in Toledo, not least because there is much more to do there than I could have seen in one day.

You will definitely have to return to Madrid before traveling on to Seville by train.

I’ve visited Toledo both as a day trip and have also spent several nights there.

As Mira has mentioned, Toledo becomes very crowded during the day as thousands of daytrippers inundate the narrow cobble stone streets of this beautiful medieval city.

Spending at least an overnight in Toledo will give you a different experience.
I’m one of those visitors who considered the evenings in Toledo as quiet and peaceful.

Yes, you’ll need to travel back to Madrid (Puerta de Atocha’s train station) to take the train to Sevilla.

If you decide to spend an overnight in Toledo, you may consider storing most of your luggage in one of the lockers at the luggage storage facility (Consigna) at the Atocha station.

Enjoy your trip!

I've been to Toledo on multiple occasions and have always stayed overnight; never a day trip from Madrid. More recently, we use Toledo as our location to get over jet lag before continuing on with the rest of our trip. The town is very pleasant in the evening after all the tourists have gone home. However, if you need to return to Madrid to catch the train to Sevilla, then a day trip may work best for you.

The only train to Toledo is the commuter line from Madrid, so it's inevitable. One way to make it an easier overnight is to pack a small overnight bag and leave the rest of your luggage in a locker in Atocha. I'd even consider taking an evening train and spending 2 nights, then morning train to Sevilla. The luggage room is just the other side of the atrium next to the long distance trains.