Attractions in Toledo

Rick's material on Toledo lists all the sights he considers significant. He has a smaller guidebook you can download to an e-book just on Madrid, Toledo, and other day trip destinations from Madrid.
No, you don't need skip the line tickets for the Cathedral or the Santa Cruz Museum.
The museum within the Alcazar is a Spanish military history museum, excellent if you're into that subject.

The Spanish military history museum at the Alcázar of Toledo is quite good and has the most extensive collection in all of Spain, including the HQ tent of Emperor Carlos V and the swords of the last Moorish ruler of Granada, Boabdil. To see the whole museum took me about 3 hrs, probably half that time if you only focus on the very important stuff. With entrance to the Museum, one can also see the Roman and Moorish ruins underneath the Alcázar.

If you would like to save some time, instead of the El Greco Museum, the Cathedral also have many works by El Greco, including the famous Disrobing of Christ. You could kill two birds with one stone and combine the Cathedral with Santo Tomé to see his most famous works in situ.

You can also watch the Ricks Steves' TV programming on Highlights of Castile: Toledo and Salamanca to map out a 1 day itinerary and utilize the Spain Guidebook on Toledo as well.

https://www.ricksteves.com/watch-read-listen/video/tv-show/toledo-and-salamanca

Great suggestions upthread. We enjoyed all the attractions mentioned on a day trip from Madrid. We are especially interested in Jewish history and were pleased with our self guided tour of the old Jewish quarter (la juderia). The Moorish style Sinagoga Dl Transito was beautiful. It was a pleasant day. We arrived by 10 am to avoid the crowd. We also recall the gorgeous Neo-Medejar style architecture of the train station!

Thanks for the comments. I have already studied the RS guidebook on Toledo but there are no estimates of how long it takes to see various sites. I am sure my men will be interested in the Alcazar!

There's a free "peek-in" for the cathedral at the side entrance but you can just buy a ticket at the store across the street from the front door and go in. In October it was a maybe 10 minute line for tickets if that and I think they were having computer trouble then. My only heads up is that they wanted a 50euro deposit for the audio guide which was a surprise. The artwork collections are in side gallery rooms so be sure to wander and explore. It's easy to get overwhelmed in that cathedral.

There's a tapestry museum that is free with your cathedral ticket across town a little bit. If the war museum is on your list that might not fit into your itinerary theme.

=Tod

PS Lots of el Greco work in the Prado as well.

I actually was in Toledo during a short 2 day shut down of the El Greco Museum. At the time, I was very disappointed, but I had the opportunity to see a lot of other El Grecos on a similar intinerary. I also missed the Alcazar and military museum. However, I was there 2 nights and thoroughly enjoyed Santo Tome, the various sites on the Toledo Museum Ticket which is only 5euro and can be bought at the Monastary of San Juan de los Reyes. I am having trouble finding the list of museums on that card, but worth considering. It included the Visigoth Museum. I really enjoyed the Museum Santa Cruz. There is often a temporary exhibit that takes up quite a bit of space, so check the website to see if it would appeal or not. It would seem that the lesser known paths appealed to me more those days. Depending on where Toledo sits on your itinerary, be sure you mark all your photos and take good notes. I can't recall seeing that cathedral, but I know that after a while all of them started to look the same. Similar might happen to you, so keep to the unique sites, IMO.
And I liked the Zocodover train across the river to see where El Greco sketched the city from. If time is short, and with 3 of you, you might just grab a cab and do it to or from the train station.

I had no trouble filling two full days in Toledo, and I skipped the El Greco Museum and Alcazar. I very much enjoyed seeing the six or seven sights covered by the bracelet deal that Rick sort of plays down (or at least he did in the guidebook I used in 2016). Most of those sights included brief bilingual tours, which I found worthwhile. I also spent a lot of time wandering the very atmospheric streets away from the Zocodover-to-cathedral tourist path. However, I'm not sure your wishlist is too long for the time you have avaoilable if you're you plan to eat lunch on the run and plan to move directory from sight to sight rather than wandering.

I struggled to navigate around Toledo using only a paper map. It's like a labyrinth. Some form of electonic map with a You Are Here dot is recommended.

Check to be sure your Toledo day is not a religious holiday. That can cause crowding at the cathedral and blocked streets (for processions) that slow movement through the city.