Segovia, Avila & Toledo

We loved our night in Segovia and would go back in a heartbeat, Avila is beautiful but we didn't spend a night here so I can't comment. We did spend a night in Toledo and was also glad we did. . In Portugal we spent a night in Obidos this was a great place to be after the day trippers had left and before they arrived! . If you are visiting Portugal I do suggest a visit to Obidos, we stayed at Estalagem do Convento. We spent a few hours in Tomar before heading to Fatima. We all really enjoyed Tomar and wished we had longer here as we would have really liked to have more time to explore the town. We spent all our time at the The Convent of the Order of Christ which was originally a Templar stronghold built in the 12th century. It was like stepping back in time and was not full of tourists. The altar was designed in a way that the Knights Templars could receive Holy Communion while on horseback. It had a amazing energy not at all touristy we even had difficulty finding the door to enter the Convent! . Although Fatima was incredibly crowded we found ourselves there on the busiest pilgrim day in October, it was still a very moving experience near the Chapel of Apparitions. . You say you don't want to spend hours exploring museums on this trip, if there was one thing I would suggest to you to do in Madrid it would be a visit to The Prado, as a practicing Catholic you would probabably appreciate the art of Hieronymus Bosch.
. Driving in this part of Spain and Portugal is very cheap and very easy, I would suggest a car to really get around.

It depends a lot on how you feel about packing and changing hotels. We sometimes rent cars, but we found Trapsatur (partly because we were staying near the office) a great way to see a lot in a day from Madrid. (Note-over two years ago!) (However, many suburban Americans hate being on a bus when they could be in control of a car. And driving is much better today with a GPS than it used to be with a paper map.) I recommend that unless you get very hungry easily, skip the optional lunch stop. The food and price are both fine, it's that it subtracts from your "free time" on a very organized day.

Thank you for your responses!

We did an overnight trip to Segovia via Avila using the bus from Madrid. And the same for Toledo on another day. Both we great in the quiet of the evening. For us the half day in Avila was enough.

Toledo is less crowded, and more evocative, at night. It was our favorite "twisty road" medieval center in Spain. Of the three, I'd recommend this most for an overnight. We really liked Segovia. I was pleasantly surprised because I often hear it disparaged (especially the rebuilt castle). I thought Segovia had more to see than most towns it's size - Aqueduct, Castle, Cathedral and an old Templar church. Avila has a great wall and is a decent place in general too. All three offer more affordable lodging than Madrid - because they each get more day traffic than overnight visitors. You can get around easily by bus but it's harder to make a daystop and move on due to limited schedules. Toledo has an AVE train to and from Madrid.