Visiting Madrid for the Second Time - Need help with itinerary and getting around

I don't understand how you think you can spend 1 or 2 nights in Toledo and
Salamanca and have time to take day trips, unless you've been there before,
in which case the obvious question is why are you going back if you aren't
going to spend any time there?

I doubt you'll find free parking that is anywhere within easy walking distance
from a tourist area. Use a map function to find parking garages and such. I
would think your hotel(s) could help with parking options.

As far as time goes, it's your trip, and I think that if you want to spend time in
those places, you should do just that. However, you are talking about 4 places
in 11 days, and they are not that close to each other. I would consider whether
you're going to spend more time going between places as opposed to being
in those places (although sometimes the journey can be the highlight).

To me, a rental car is definitely the way to go for the towns you want to visit in the timeframe you have, and the drive is easy. Driving time each driving day would be about 2 hours. Parking is fairly easy to find, but it does help to look up parking lots before going over and bookmark them to your navigation app so you can go right to them. In Toledo there are a number of free parking lots, but they are alway busy. Hotels with on-site parking are beneficial, even if you need to pay. Hotel parking will cost around €15 a night.

You could do your trip using trains, but you’d need to return to Madrid to get to the next town.

Hotels I’ve stayed at in Toledo with parking are Hotel María Christina (paid) and the Parador a couple miles outside of town (free). When we stayed at the Parador in 2024 we drove into town and four of the free lots I had bookmarked were full and we ended up parking in a free lot behind the train station 1 mile from the historic center.

In Cuenca we stayed at the Parador (2014) and it had limited free parking as well as a paid parking garage. In 2022 when we visited as a day trip we parked at Paseo del Huécar Garage. You want to park near the historic center if possible.

Although I haven’t stayed at it, the Parador in Salamanca has free parking. It’s a mile from the cathedral. My last trip to Salamanca was in 2007, but I can’t remember the hotel we stayed at on that trip. It too had on-site parking.

I recommend not driving into the historic centers of those towns due to pedestrian and restricted driving areas.

Since driving times between those towns is nominal there will be time to make stops en route. If you want some suggestions send me a PM and I’ll provide some ideas.

Have you been to Toledo? We spent three nights in Toledo and spent all our time visiting Toledo. There is so much to see there. It is a stunning.

You might consider putting all your Madrid days at the end. So, when you arrive the Madrid airport take a train somewhere, maybe Toledo? Enjoy Toledo and then when you are done, pick up a car (if that is the way you've decided to travel) and continue your trip.

We always use google maps and use the "nearby" function to locate parking (or stores, restaurants, pharmacies, etc.)

In terms of your allocation of days, Madrid is beautiful and lively. They also have world class art museums. If you are interested in art, spend time in Madrid. Otherwise, to be honest, I find other cities in Spain to have much more energy and historical significance.

Have you been to Segovia? It is a day trip from Madrid with a gorgeous Roman aqueduct.

In terms of transportation, I find trains and buses so much more relaxing than driving. I always first see if I can get to where I want to go on public transportation in a relatively efficient way. If I can't, then I look at renting a car.

It seems like a rather rushed itinerary to me.
I'd drop one place.
Salanaca is lovely, but on a different side of Madrid than Cuenca and Toledo.
Segovia is an easier day trip from Madrid.
I also would not have a car. Unless staying in hotels with parking, you'll spend too long finding car parks.

I agree with LinC..too much time in transit, not enough time in each destination...

And I'd put the Madrid stay into one time slot--not ahead of to go into Madrid and overnight more than once....go straight to Toledo on arrival, or straight to Cuenca...

For me, flying from NYC, the first day in Spain is always a wash..I'm too tired to do anything except go for dinner..

Thank you ALL for your responses. You've given us ideas to think about as we refine our travel plans. We sincerely appreciate it!

I have a cousin who just moved in to Madrid for studies so we're spending some time with him.

shoeflyer & julesm: We've been to these cities before. The reason why we are renting a car is to be able to stop at towns/villages along the way that might interest us before we get to our intended destination. Indeed, the journey could be part of the highlight!

Jaimeelsabio: I'll PM you.