If you had to pick 2 of these to visit, which ones would you choose and why?

I did that loop last April and stayed in all 3. Why would you need to choose. Avila is on the route between the two " S " towns and can be enjoyed in 2 hours time. Of the 3, Salamanca was my favorite.

We will have little time and want to cover lots of different little cities.. I love the idea of spending 2 hours in one city and heading to another..
The initial idea is to leave Madrid early in the morning, head to Segovia, then Avila and overnight in Salamanca..
Is that doable?

Thanks!

Yes.

I agree, but get going early and be in Segovia by 0900 & plan lunch in Avila.

Hi there,

Also a similar question. We'll be in Toledo for two nights (the wed and thurs of holy week) and then plan to leave Friday for Santo Domingo de Silos, Segovia, Avila and Salamanca over the next 3 days.

Doable? And any particular recs being that this will be Holy Week?

Thanks,
LCS
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Ics
You will be travelling in peak vacation time. Your main concern should be to have your rooms properly booked and confimed.
As far as the travel distance, time involved, I find it tight but doable.
You can do in one day Avila and Segovia ,first day, then from there drive to Santo Domingo de Silos second day, and Salamanca,third day. I presume you want to end in Madrid and you have three full days. With this plan you will have to drive, change hotel and visit all in the same day, and due to Eastern holiday you will have to share the main sites with many other people.