Madrid/Toledo November? With Kids 9 and 7

I would wait until summer and take the longer trip. Two full days of travel for 4 days on the ground is kind of brutal.

Only you know if your kids will be “flopping around” wishing for a pool.

For a long weekend, stick to one city and that’s it especially with small children who need to get accustomed to the time difference and then re-accustomed back to EST in time for school.

Like you, I love long weekend trips to Europe as it’s convenient when you live in the Northeast but even so, I only stay in one place because I don’t want to waste precious time in that long weekend traveling from place to place.

I agree. If a longer trip is an option, I would wait. However, if you plan day trips from a single base next year, I strongly encourage you to explore estimated driving times on the ViaMichelin.com website. I think a single base will be quite limiting.

If the opportunity to take the trip is attractive, and you’re up for it, i say go for it!

I would argue that there’d be plenty to keep y’all busy in Madrid, and Toledo might best be left for another trip.

Go! I'd keep it simple. I think that there is enough in Madrid for the time that you have. Personally, I'm not passing up opportunities to travel - even if it's a short trip. We were in Madrid in late November last year and it was very festive.

To me, what the children like to do and see would be a determining factor. If they like old bridges, buildings, and walking outdoors, I think they’d like Toledo. There are enough churro & chocolate places in Madrid to keep them occupied and they’d probably enjoy Retiro Park by the lake, assuming the weather is nice. My guess however, is they would enjoy it more when the weather is warmer.

Another vote here for postponing until next summer. We just got back from Spain and the jet lag was intense (lucky you though, were on the west coast). Also Toledo seems smaller and not as exciting for kids (but we haven't been there ourselves yet).
Our youngest was 10 I think when we went to Madrid. He enjoyed it but 7 is a lot younger. Also my kids are foodies (from a young age!) so the unusual seafood at the market and of course churros and chocolate were a highlight for them! We also the places you mentioned and also the castle there in Madrid and a flamenco show. They were bored pretty fast with that-choose the shortest one! I may be a terrible mother, but we peeked into the bull bar and they were fascinated and horrified in equal measure! I like the idea of balancing cultural sights out with swimming and enjoying parks next summer. (oh full disclose they liked Barcelona better than Madrid)

I love this forum! Thank you for your insight, honesty and enthusiasm. I'm trying to balance this desire to explore the world with the family (esp. after 2 years of lockdown) with the reality of where they are right now developmentally. So tempted to just go but also wondering if a longer, more deliberately planned journey might make it a better experience. Appreciate everyone's comments!

I traveled with young children years ago and found that my Son doesn't remember much that he saw prior to age 10.

The one thing that elementary school kids can't handle much is spending a long time in museums. I remember my 8 year old Son when entering the ancient Greek and Roman section of the Lourve said "OH no, more naked statues." We had spend 10 days in Italy prior to Paris.

After 30 minutes kids that age want to leave a museum.

I remember my kids loved our gondola ride in Venice, going up the Eiffel Tower and loved riding on trains. My Son was in AWE of the Sistine Chapel at age 8 and wanted me to explain to him all the frescoes on the walls and ceilings.

It is good to try to explain to them the significance of what historical places or art that you show them.