Day Trips from Madrid & Barcelona

I'll only address Toledo (I have not been to Montserrat).

First, I see no need for any sort of guide when visiting Toledo. The city is easy to navigate, major sites are not hard to find, and the city itself is actually the major draw.

Toledo looks like the perfect day trip: it's a quick, easy bus or train ride from Madrid. That's why vast throngs of people go to Toledo, as a day trip, from Madrid. And that - because virtually everyone does Toledo as a day trip - is why doing Toledo as a day trip is a mistake.

Toledo is very popular. It's crowded - very crowded - mid day. There are too many people crammed into its streets from 10 am to 4 pm, and IMHO that ruins the experience. But after 4 pm and before 10 am, the place is empty, magical, and a lovely, wonderful experience.

So all you have to do to turn a bad experience into a great one, is to invert your scheduled time there: don't go mid-day, go outside of those hours. Arrive mid-afternoon (say, 3-4 pm), enjoy the wonderful old city free of crowds into the evening, spend the night in the old city center, get up early, enjoy a few more hours in the morning, then head back to Madrid around 10 am, as you watch the city streets fill up and overflow with tour group crowds.

True story: a relative took his family to Spain. Before the trip, he asked me for advice. I gave him the above advice for Toledo, he said he would follow it. After he got back, I asked about his trip...
Him: "Spain was great, you were right!"
Me: "How did you like Toledo?"
Him: "Oh, it was awful. It was so crowded - we hated it!"
Me: "Really? And you spent the night there?"
Him: "Oh, no - we wanted to save a few bucks by sleeping in Madrid - we did Toledo as a day trip...but I wouldn't go there again."
Me: Falcepalm...

We were in Madrid and Barcelona last year in early October, however, we did not visit to Montserrat so I can't help you there. For Madrid, we did visit Toledo and did so on our own using RS guidebook. It is easy enough to tour on your own. As for trains, you don't need to book in advance, however, I would recommend booking at least 24 hours prior, maybe 48 hours. Because we booked the night before, we did not have the best options and couldn't get a train until late morning and returning mid-evening. Our preference would have been to go in the early morning.

We did take another day trip from Madrid to combine a wine tour of Ribera del Duero and Segovia with Wine Bus: https://www.winebus.es/en/. It was one of the highlights of the trip. The region is home to some of Spain’s most sought after and applauded wines. Riberas are crafted to age, developing complexity over time, yet balancing acidity and generous fruit, they’re unequivocally food-friendly wines to drink young. It is most comparable to Cabernet Sauvignon. After the trip to the winery, we had a lovely lunch in a small town in a local tavern, and then visited Segovia. We ended the trip on a bluff overlooking the castle and drinking a glass of wine. Segovia is a great place to visit and you can do it on your own, but if you want to combine wine tasting with a visit, a tour is your best option.

Have a great trip,
Sandy

David's advice for Toledo is accurate, but I found that if I got a couple of blocks off the path between Zocodover Square and the Cathedral, there were far fewer tourists even at mid-day. (I spent several nights there; love the place, though some might complain that it is too dead at night.) That was in 2016, and I'm sure the city has become somewhat more crowded during day-tripping hours. It would be prudent to buy the train tickets ahead of time, because trains most definitely do sell out. Rick specifically warns about the late trains returning to Madrid. Having paid for a hotel room in Madrid, you will not want to be marooned in Toledo.

I imagine Enric will soon notice this thread and provide a link to a very detailed post about doing Montserrat on your own. It seems to be quite easy to do that.

Here's Enric's earlier thread about Montserrat. The "Getting There" section is several posts from the top.

We had a great time in Madrid and Barcelona in October 2017. We took several small-group day trips and a private tour to Tarragona. We probably could have done them on our own less expensively, but I wanted a little pampering on this vacation.

I highly recommend this company:

https://spanish-trails.com/

I followed Enric's instructions for Montserrat and the day went perfectly. I wouldn't take a tour because I enjoyed the flexibility to manage the day as I pleased. We took a funicular up to the top of the mountain and had a lovely time doing some hiking. Then when the crowds thinned we went back to the monastery again.

Do you have Rick Steves Spain? In it, he details all the logistics of doing these day trips on your own. You can, of course, take a tour if you wish, but there's no "need" to.

For Toledo, I'd definitely book the train tickets in advance, as this is a popular route. However, if the train you want is sold out, the buses are frequent and don't take much longer, so these can also work.

Don't go to Toledo on a Monday, as many things are closed (a mistake I made years ago).

I followed Enric's instructions for Montserrat and the day went perfectly.

Another vote for this. My visit to Monserrat was one week ago, and was pre-booked ( the "Montserrat Tot" package) before departing for Barcelona. I also would advise against an arranged tour. There's plenty to see on your own and as you see fit.

For me, part of the fun was getting there, including the aeri and then the funicular to Sant Joan. The only disappointing part, from my perspective, was the train ride out to Montserrat. I was thinking it was more of a non-stop ride, all on the surface! A minor quibble in the scheme of things.

Hopefully it will be cooler for you in October... the forecasted high at the monastery the day of my trip was 34C. Mercifully, there was a nice breeze on occasion out on the trails above the funicular station.

Enjoy, it is spectacular.

Just to add that in October temperatures in Montserrat can get colder quite easily. Take a jacket with you.

Read Enric's posts. They are spot on!

I did Montserrat on my own.....no guide except for my RS guide book. I did not buy my train tickets in advance.

Read Enric's posts.