THANK YOU and also need advice (Segovia/Avila/Toledo/Madrid)

Segovia is an easy day trip to Madrid. I wouldn't waste time changing from the Madrid hotel to one in Segovia.

You will need to confirm current schedules and prices, as my visits to Spain were pre-pandemic, and some things may have changed, but...consider this:

1. Train from Madrid to Toledo (plan to arrive in the afternoon). Enjoy Toledo, spending the night there.
2. Rent car in Toledo (depart late morning), drive to Avila. Play in Avila for a while. Drive on to Segovia, arriving afternoon. Drop off the car on arrival.
3. Enjoy Segovia, spending the night there.
4. Train from Segovia back to Madrid.

In my experience, both Toledo and Segovia are perfectly connected to Madrid by easy, convenient trains. That is a double-edged sword, of course, because that makes them perfect day-trip destinations, thus crowded mid-day (but you can still take advantage of the excellent train connections). Avila was (and probably still is, but is worth checking) less well connected by rail. When I last did these cities, the logistics favored one-way trains between Madrid and both Toledo and Segovia. Avila was the outlier. I took the train from Madrid to Toledo (afternoon train, so as to time my arrival to miss most of the crowds). After my time in Toledo (spending the night there), I rented a car, and drove from Toledo to Avila (maybe 2-3 hours?), played on the wall for a couple hours, then drove on to Segovia (another hour or so), dropped the car there on arrival. After my time in Segovia, I took the train back to Madrid.

The day where we drove from Toledo to Avila to Segovia was a bit of time in the car, but it seemed to be the only efficient way to "do" Avila on the way between Toledo and Segovia without having to go through Madrid. IIRC, the rail network is laid out in a way that required all trains to go through Madrid (not surprisingly, the trains are set up primarily for locals, not just for tourists, and we wanted to avoid doubling back and going through Madrid to reach Avila and then again going through Madrid to get to Segovia). Of course, the costs of renting a car is not trivial, but it does give you a lot more freedom to do creative routings, like this one.

Hope that helps.

Segovia is an easy day trip to Madrid. I wouldn't waste time changing
from the Madrid hotel to one in Segovia.

But that is exactly why both Segovia and Toledo are so crowded during the mid-day -- and why they are so much better when the day-trippers are all gone. Because everybody says "oh, it's too much trouble and more expensive to keep changing hotels, I'll just stay in Madrid."

I have a family member who was planning his first trip to Spain. I urged them to spend the night in Toledo and Segovia, rather than doing them both as day trips. After their trip, you want to hear our conversation?

Me: Hey, how was your trip to Spain?
Him: We liked it.
Me: Did you go to Toledo, Segovia?
Him: Yes.
Me: How did you like them?
Him: Meh, not so much. They were really crowded!
Me: Did you stay overnight there as I suggested?
Him: Nah, the hotels looked kind of expensive, and it was just easier to stay in Madrid.
Me: D'oh!!!! (facepalm)

Sure, it's nice to not have to change hotels. And yes, hotels will be less expensive in Madrid when compared to hotels in Toledo and Segovia. And you'll have to deal with carrying your bag a couple times. But the difference in the cost of the hotels is pocket change. The "price" you pay is not just the hotel bill and the inconvenience of relocating. Sometimes it makes sense to not do the obvious (because so many other people do exactly that).

That's just me, others may place a higher priority on saving some money and skipping the minor relocation tasks. But I will share that, years later, I can not remember what the hotels cost, or any hassles experienced changing hotels. I do remember wandering those streets when they were quiet and free of crowds. Just my 2 eurocents.

Thank you so much @David! I’ve read, and thought about your suggestions and frankly LOVE them! This is the best scenario suggested yet and I think I’m going to plan this!
-leave Madrid via train to Toledo and stay 2 nights. Grab a rental car
-visit Avila for a few hours and end in Segovia. Return rental car and stay the night
-leave Segovia and go to Madrid and stay the night.

TBH- I love this plan. Changing hotels doesn’t bother us at all (we actually enjoy it) and we pack light so taking trains with our luggage won’t be a big deal.

@David- where would you suggest the easiest location would be to pick up the rental car in Toledo and drop off in Segovia?

Thx again!

I don't recall the rental car locations specifically, but I would just apply the standard logic for all driving in Europe: try hard to avoid driving anywhere in the old center of cities (you can usually tell what parts of a large city are "modern" and which are "OMG stay-out-of-there!" with a quick look at a map). Driving in the "modern" parts of big cities can be stressful, too (hello, Paris?), but pales in comparison to trying to drive through twisty, narrow "streets" no wider than an oxcart, that were laid out in the middle ages. Look for an agency that has an office outside (or at least not deep inside) the old center, both for pick-up and drop-off.

IME it's less stressful to drive OUT of an old center (though still not ideal) than it is to try and drive IN to one -- even with GPS and a helper/navigator flying right seat, the navigation is trickier when you are trying to find a specific address/location (and then trying to find parking). When departing, all you need to do is navigate OUT of the old city, then it quickly becomes less stressful once you see signs for major highways, "ring roads" and other things that are more familiar. "Just get out, the specific direction isn't critical" (for a while).

So, look for places on/near the edge of the city centers, not smack-dab in the middle of the old centers. Ideally close enough to your hotel that it isn't a major project to find it and lug your bags there (a short taxi ride may be needed). The good news is that both Toledo and Segovia are large enough and touristy enough that there should be multiple rental car locations to choose from. Locate your hotels first, then shop for a good car pickup/drop-off point and strike a reasonable balance between close-to-hotel (which you probably WILL want to be in the old center, if possible) and low-stress driving.

You're in for a great adventure. Enjoy it!

If you decide to rent a car in Toledo, there’s an Avis facility across from Hotel María Cristina (a nice hotel with its own parking garage. The Enterprise facility is by the train station and there is a Europcar facility near there too. The drive to Ávila is about 2 hours and continuing to Segovia is another hour. Since much of the drive is via the old “nacional” roads, you’ll get to see more of the countryside than you would if it was all interstate driving.