day trip to Toledo or stay overnight- suggestions please

This is a tough call. The “standard” advice here and in ricks book is to stay overnight because the town is peaceful and beautifully lit up at night. I agree, it looks great at night. During the day it is packed with day trip visitors so at night it certainly is quieter.

The drawback is that...how much peace and quiet is too much? The flip side to peaceful is deserted and in my opinion Toledo at night can fall into that category. The lively late-evening paseo and restaurant scene you enjoyed everywhere else in Spain is absent. Many restaurants are closed, and the squares aren’t full of life. They are empty.

So...do you want beautiful, empty streets all to yourself on your last night or do you want to walk and hang out in a cafe on a populated square?

I found Toledo to be one of those places that just wasn't real pleasant to be out in during tourist prime time. Way too many people concentrated in too small areas - narrow streets etc. We didn't find the streets empty at night, there were people about.

I doubt that Toledo will be overrun in December unless the day of your visit is a local holiday or festival day. During my late-May visit in 2016, the crowds were prdtty much concentrated between Zovodover Sq and the cathedral. The only crowded site was the cathedral--probably made worse by the religious holiday. However, I skipped the El Greco Museum.

My reason for spending multiple nights in Toledo was more about having time for additional sightseeing than crowd avoidance. I would agree that even in late May the city was pretty quiet at night.

There is another potential issue, though: You may find that public transportation back to Madrid doesn't start early enough to be sure you'll make your flight. Your airline will probably suggest that you be at Barajas 3 hours before departure time. If this turns out to be a problem, you can travel Barcelona-Toledo-Madrid. It's always a good idea to schedule your departure city at the end of your trip.

'acraven's' recommendation above is exactly what I would do: Barcelona-Toledo-Madrid. Take the AVE (high speed train, book well in advance to get a good price) from Barcelona to Madrid's Atocha station, where you switch to the commuter train (buy ticket there, no price changes) to Toledo, only 30 minutes more, and spend the night, returning to Madrid the next afternoon for the remainder of your visit.
Madrid and Toledo will be chilly to cold. You may get snow - how picturesque that would be! Toledo in snow!
Enjoy your visit!

thanks everyone for you great , well thought out, suggestions. it is much appreciated.

I too agree with spending a night in Toledo with the Barcelona -Toledo - Madrid order. I enjoyed walking the streets at night when they were close to be deserted. It’s a great time to get some nice photographs and have a dinner with more locals than tourists. We always stay at Hotel Maria Cristina, near the bull ring and about a 10 minute walk from the Puerta Bisagra and tourist information center. From there you can either walk up the hill to the historic center or take the nearby escalator.