Toledo stay

One is good, two would be great.

It depends on what you want to see and do. You can see most of the sights one day if you don't linger at any. Note that Toledo is built on steep hills, similar to San Francisco, so walking takes a bit longer.

Hard to say without seeing how it fits into your overall itinerary, mainly what are your travel days like before and after. Toledo has some nice sights, the town is beautiful, a couple nice museums, el Greco related sites, a cathedral. If you would be arriving later in the day and need to leave by noon, then do two nights, even if you maximized your days in Toledo, it is still worth two nights.

Toledo can get busy during the day, lots of groups do day trips, so like many places like this, evenings can be wonderful after the crowds leave. Lots of great restaurants and little bars.

If you've got the flexibility definitely 2 nights. And, there is enough to do that more wouldn't be wasted - especially if you don't go all day, laying low during peak tour group time. As I recall most places of interest are open what we would consider to be late.

I agree with Chani. The main sites can be seen in a day, so depending on what time you arrive in town and what all you want to see will be the determining factor. There are a couple lesser sites seldom mentioned; the military museum (Museum of the Army) at the Alcazar and the Roman Circus that is a short walk from the center of town. It’s outside of the Puerta de Alfonso VI. Not much of the circus remains and it’s more a park. The museum was very much worth a visit. There is also a sword smith that you can watch make high quality swords, not the tourist ones. Then there are the legends surrounding the bridge of San Martin and the pozo amargo (bitter well). The bridge is beautiful and is on the backside of the town. The well is a short stop, near the cathedral, and makes for nice nice photo.