Madrid Day trips - Segovia and Toledo

If you rent a vehicle then parking becomes a problem. Do your research and check on where to park. I have been to Toledo and Segovia twice. Toledo has virtually no good place to park close to the city.
Not sure abut Segovia.
The last time I did Segovia, we took a group tour from Madrid that Included Segovia and Avila. It was a very nice tour.

The train is cheap and fairly quick.

You’d have no trouble getting a taxi in either town. I believe the train station in Segovia is not right in town, so someone more knowledgeable can respond about it. The train station in Toledo is a mile from the historic center.

I’ve always had a rental car and never visited either town as a day trip. There are a number of pay parking garages (very close to the historic center), but there are also free parking lots in each town. You would need to look them up in advance since they are not well marked, if at all. Some may be a little further from the historic center than you’d prefer. In Toledo in 2024 we ended up parking in a free lot along a street behind the train station since the closer free lots were full.

Contrary to what geovagriffith stated, in Toledo there is a parking garage just past Zocodover Plaza and the Alcázar. Enter the historic center via the Bisagra gate and drive straight up the hill. Just past the plaza the road turns left and the garage is on the right.

When you get to Toledo or Segovia, there's going to be a giant line of taxis outside the train station, no Uber needed.

I definitely wouldn't want to drive a car or van around a medieval city. Just get a taxi to the city center from train station and get a taxi to catch the train back to Madrid. It's that simple.

I took a day trip from Madrid to Toledo. Just outside the exit of the train station, there was a line of taxis and metal barriers showing where people should line up and wait for the next taxi. The same thing was at the other train stations I was at, in Spain. When you get to the front of the line, you get in the taxi at the front of the taxi line. I took only one taxi ride in Toledo, to the thing I thought looked appealing that was furthest from the train station. If you take a taxi, you could probably ask for the taxi company's phone number so you could call it in case you want a second ride back to the train station or somewhere else. Or see if the number is on the side of the car. I drive like a "normal" person near my home in SE Michigan. I have taken 6 total solo trips to different countries in Europe so far. I didn't rent a car in Spain or any of the other countries. I suppose your group of 6 might have to break up into two groups if the only taxis available have just space for 4 passengers. I don't remember if some taxis were mini-vans that could seat 6 passengers in addition to the driver.

I’ve done both as day trips from Madrid, each by train, and I never felt the need for a rental car.

Toledo: The AVE train from Atocha gets you there in about 30 minutes. From the station you can take a short taxi/Uber ride or the escalators up into the historic center. Once you’re inside the old town, everything is walkable — though the streets are hilly. Parking in Toledo is limited and usually outside the old walls, so a car tends to be more hassle than help.

Segovia: The high-speed train takes about 30 minutes as well, but the station is outside town. A local bus or taxi/Uber will get you into the center in 10–15 minutes. From there, the aqueduct, cathedral, and Alcázar are all within walking distance. Again, driving into the historic core is tricky, and parking is not convenient.

In short, trains plus a short taxi/Uber connection work well for both. With a group of six, you might find a van transfer cost-effective, but unless you want to detour into the countryside, I’d stick with rail — it’s fast, efficient, and avoids the stress of parking in medieval centers.

To elaborate on the escalators Belisarius45 mentioned, there are two escalators in town. One is over by the Alcántara bridge and goes part way up the hill to the historic center while the other is just past the Bisagra gate and goes all the way to the top. Both are about a mile from the train station. A taxi to Zocodover Plaza would save some walking.

Thank you all! It’s very helpful for our planning!

There is an underground public parking garage right next to aqueduct in Segovia. It’s very convenient.

We took the train to Segovia two years ago. A bus meets the train. It takes you to the aqueduct. Just need to verify times and location of return bus to the train. It is across the street from where you get off. From the bus it is an uphill hike to the cathedral and castle. You’ll do a lot of walking. It will be a busy day trip. Segovia has gotten much more touristy since our visit 15 years ago. We spend a couple of nights on each visit. There are no more free tapas with a purchase of a wine or beer. LOL!