Toledo & Segovia Day Trips from Madrid or overnight trips?

My opinion, Segovia can be a day trip, Toledo is worth an overnight if you want to
linger a bit.

The cost savings needs to be weighed against the hassle of packing up and moving
to a new place potentially twice. Maybe save the possible Toledo overnight until the
last night so you don't go back to Madrid and check back into another hotel. You'd
have to most likely store luggage at the hotel if you plan to get there before check-in
time.

In Toledo, the train station is located outside of (and below) the town. There are some
hotels that do not require you to get to an escalator to go up the hill into the main
area, but there is some overhead no matter what. It is a bit of a walk or there is a bus.

I’ve always done both as overnights, but I’ve always had a rental car.

I question the Segovia-Ávila day trip. They are in different direction coming from Madrid and I don’t think they are on the same train line. I believe Ávila is along the line to Salamanca.

In Toledo we stayed at Hotel María Christina a couple times. It’s about a mile from the Bisagra gate. To the right of the gate (an arch) is an escalator to the upper town. The train station is also a mile from the escalator. In 2024 we stayed at the Parador, but it’s outside of town.

I haven’t been to Segovia in a while so cannot make an informed hotel recommendation.

We flew into Madrid and had a driver take us to Toledo for first 2 nites
Then train back to Madrid and on to Sevilla and Andalusia
Put all of our Madrid nights at end before departure flight

There is a lot to see in Toledo, haven’t been to Segovia

I travel to Toledo twice as day trips as well as Segovia both using a bus.

Have not been to Toledo but, in 2024, we arrived in Madrid at the start of a trip focused on Asturias, Picos de Europa and La Rioja. On arrival we picked up a car and drove to Avila, walked the walls, then went on to Segovia for the night. Would recommend doing both. We always have a car, but it looks as though you can take a train or bus to Avila in less than 90 minutes, then bus from Madrid to Segovia in less than an hour. The train back to Madrid from Segovia takes less than a half hour. It was lovely to be in Segovia in the evening and morning after/before all of the daytrippers. We stayed at Aurea Convento Capuchinos which was conveniently located for exploring the city but I have no clue about walkability from train or bus stations. Have a great trip!

Thank you to all the respondents for their suggestions and recommendations. I sincerely appreciate the valuable advice.

For Toledo overnight, doing it at the end makes sense. Are there reliable transportation options available for Madrid airport for our return flight: such as direct airport shuttle, private car/taxi, Uber, etc. or We will need to take the HSR back to Atocha and change to commuter train or bus?

For overnight stay in Toledo, any recommendations for good hotel? I found the Parador, but it is out of town across the river. So I am not sure how easy it will be for the sightseeing. Any feedback?

Regards,
CDM

My mom & I enjoyed our stay at Hotel Santa Isabel in Toledo several years ago.

Just make sure your room is not on the third floor right under the roof terrace.
When we were there we spent our first night in a nice room on the third floor with a lovely view of the cathedral. The following morning we asked to be switched to the second floor due to the noise of moving metal chairs coming from the terrace above.

Wishing you a wonderful time in beautiful Spain!

Thanks Priscilla, I will follow up.

~ CDM

Ask your hotel for recommendations for airport transfer or use a service like Welcome PickUps.com

Otherwise it would be train back to Madrid first
Not sure if there is a bus

The drive from MAD to Toledo took about an hour

We stayed at Hotel Carlos V-very nice at a great location
https://www.carlosv.com/en