Day trip to Toledo

I’d make a whole day of it. Get there mid-morning, give yourself time to enjoy the city, browse the shops & markets, visit the cathedral and the museum and just enjoy the place. Maybe have an evening meal or late afternoon tapas. From memory*, I don’t think you need to book a specific time for your train back to Madrid so just see how the mood takes you.

(*it was quite a few years ago that I went.)

Yes, you will get many opinions on your plan. Here's one:

Toledo is beautiful and absolutely worth a visit, but it suffers from a common European affliction: Too many tourists. To be specific, too many tourists who have the exact same plan as you do: Using Madrid as a base, make a short day-trip to Toledo. The result is crowding during the mid-day. From late morning to mid-afternoon, Toledo is jammed with tourists. Conversely, outside of those hours, it's delightfully empty, peaceful, magical.

You can beat the crowds and benefit from the magic easily: arrive in Toledo mid- to late-afternoon. Enjoy the city as you see the crowds fade away, everyone piling back onto their tour buses and climbing aboard the train back to Madrid for the night. By evening, you will have the nearly empty city pretty much to yourself. Enjoy the late afternoon and evening hours. Sleep in a hotel in the old city. After dark, the only sounds you'll hear are your footsteps on the cobblestones echoing through the deserted streets of this medieval city. Get up early, go out and enjoy the empty city for a few more hours. By mid-morning, the fleet of tour buses will roll up and empty out, filling the streets and sights with day-trippers. That's your cue that it's time to leave.

Yes, it's a little more complicated than just basing in Madrid and taking the very convenient train to spend a few crowded hours there. But the difference in quality of your experience will be, well, day and night. It'll be worth the expense and minor inconvenience of moving for one night.

Pretty much every package tour to Spain (and most independent travelers) does Toledo as a day trip from Madrid. You can choose to be one of the people who experiences Toledo at its crowded worst, or you can be one of the clever ones who gets it at its empty best. Some places in Europe that have become to popular benefit from this simple strategy. Toledo is a perfect example. Be there when everyone else isn't, and you'll be glad you did.

We did a day trip to Toledo. We saw the sights you mention and walked around, too. Another thing we did that we really enjoyed was to take the little train. It takes you outside of Toledo to where you get fantastic views of the town--views that El Greco painted.

We did a day trip from Madrid in 2016 and arrived by 10 am and left by 3 pm. At that time it was not crowded. That said, if we were going now we would consider an afternoon trip or over night stay. We planned a stop at the Reina Sofía Museum when we returned to Madrid. If interested it was a short walk from the train station. This link may be helpful in your planning: http://www.planetware.com/tourist-attractions-/toledo-e-cast-tol.htm
Enjoy your trip!

I did a day trip also and enjoyed it very much, it was in November though. Don’t forget that El Greco’s famous painting of the Burial of Count Orgaz is in the chapel of Santo Tome and not the actual museum. Also, I thought the marzipan was really good, I bought it at a place in the main square next to the arch and enjoyed a piece or two every day.

David’s description of staying later in the day is exactly what we experienced. We stayed two nights in Toledo - our day of arrival from the US and one day to enjoy the city. Our hotel, Hotel Pintor El Greco, is in the Jewish district, and we were able to enjoy the less busy spots during the day and the wonderful ambiance in the evenings. We didn’t even realize that Toledo was a busy tourist spot until we walked mid-afternoon the second day over to that section of Toledo.

So, my recommendation from your two choices would be to go a bit later and plan to stay into the evening.

Your plan to eat about 2:00 PM (14:00) is about right, the better restaurants will adhere to Spanish meal times, with the main meal about 2:00, places shutting down about 4:00. Things will be pretty dead after that and your meal options will be snacks and fast food until 8 or 9.

Make sure you plan your return, buying a round trip ticket. The trains back to Madrid can sell out during peak season, best to have a seat.

I think the ideal visit to Toledo would be to spend at least one night there. Toledo is very, very crowded during the day with daytrippers and large tour buses. The city is beautiful at night when it is illuminated, and less crowded when the daytrippers have left. We visited in mid-September and Toledo was active at night. Families were in Zocodover Square having ice cream and children riding their bikes. Much fewer tourists. Very enjoyable.

However, if you can't stay overnight, visiting Toledo for the day is better than not visiting Toledo. And I also recommend the little train that takes you outside the city where you get gorgeous views. You pick up the train in Zocodover Square.

This was my outline for an intense (some will say rushed) day in Toledo.

I visited in January 2020 so my crowds were thin.
Ensure you get to Santa Cruz for its opening at 10am and you will get the most out of your day, time wise.

10:00 Santa Cruz Museum
11:30 Cristo de la Luz
12:15 Santo Tome
13:00 Lunch
14:00 Synagogues (one or both depending on time!
15:30 Monastery San Juan de Los Reyes
16:30 Cathedral (closes 18:00)