Sounds like a great trip. As I see it, you have about 5 days to visit Avila, Segovia, Salamanca, and Leon. Great choices, even though I have to wonder about including Leon on this trip.

I suggest that upon arrival to Madrid, hop on the car and head out to Avila. In Avila I would recommend the Parador IF you choose to stay there. Avila, in my humble opinion, is the most impressive walled city I have ever seen (been to Rothenburg; not even close). Aside from the impressive walls, a lot of Avila's sightseeing is related to Santa Teresa de Avila, a Catholic Saint. So, if that is not at the top of your sighseeing choices, I would head out to Avila, enjoy the sight of the walls and continue on to Salamanca to spend the night and one day of sightseeing (May 19-20). In Salamanca we stayed and HIGHLY recommend the Hotel NH Palacio de Castellanos. Amazing location, gorgeous hotel, great value (back in 1999 we paid $100/double). Spend the next day sightseeing and then head out to Leon (May 21-22). IF the Parador is booked (happens frequently) a good alternative is La Posada Regia, a gorgeous hotel in the middle of the historical center. Back in 1999 we paid about $80/double (Room 301); loved every minute of our stay in Leon. Do mot miss a visit to the Cathedral and the Royal Pantheon (some trivia; the bank building across from La Posada Regia was designed by Gaudi; the locals hated the building as it resembles a Scottish castle). If you choose not to stay at La Posada Regia, visit their restaurant; great food, exquisite service). From Leon head back to Madrid via Segovia (May 23-24). I am an engineer, so the Aqueduct in Segovia was absolutely mezmerizing to me, but there is a lot of other things to do and see in Segovia. We spend a couple of nights in a Hostal ($35/double). It was walking distance to everything, clean and comfortable. We could had paid more, but this Hostal came recommended and it was all we needed. We splurged on meals, and there are a lot of great restaurants to choose from. If you need more information, please feel free to ask away. Have a great trip. By the way, while it is most likely that Madrid will be hot, bring some layers with you as the nights in Leon can be quite cool, even in late May.

Hi artlover,
Last summer we did a 2weeks+ trip in Spain that included Salamanca and Leon. these are now 2 of my favorite cities in Leon.
As Chatters, in Salamanca we stayed for 3 nts. in NH Palacio de Castellanos. We really liked it and loved all that Salamanca has to offer. The hotel was very reasonable, approx. 90 Euros.
We then went to Leon via Zamora( stayed in Zamora 1 nt in the Parador) and stayed for 2 nts in the Parador San Marcos in Leon. Outstanding!!!! Following the recommendations of Maribel, ChadL and other posters we stayed in the new annex of the Parador. Really nice rooms , with a balcony overlooking gardens/ river, and a great modern bathroom. Make sure you are outside the cathedral at midnight as they light it up from the inside and you can see all those beautiful color glass windows all lit up! We had dinner at the Posada Regia and it was great. The other night we had dinner at the Parador, also very good.
We did this whole trip by bus and I can't say enough about how easy it was. If you need the names of the bus companies let me know and I'll try to find it. I'm pretty sure from Madrid to Avila/ Salamanca it was Auto Res.

Chatters and cruiseluv,

You are truly amazing! Thank you so much for responding so soon and with so much great information.

Chatters, yes, I too was thinking at first that maybe I should save Leon for another trip, but I'm so drawn to it, and while I usually opt for "slower" travel, I think really want to go.

cruiseluv,
Thank you for the information about the bus--yes, if it's not too much trouble, if you could get more information I'd really appreciate it.

So, based on what you've said, I've come up with this as a tentative iternary:

May 19--arrive Madrid 12:00, take
bus to Avila, night at parador

May 20--Avila to Salamanca, night
at parador

May 21 & 22--Salamanca to Leon
2 nights parador

May 23--Leon to Segovia--parador

May 24--Segovia to Madrid

May 15--leave

If this is doable, I could get the 5 day parador pass which is a huge savings (assuming I can get the reservations).

Thanks so much for your tips. I'll probaly have more questions to ask yet.

Hi Artlover,

The bus co. for Madrid to Avila and avila to Salamanca is www.auto-res.net.
The following website ref has the schedule for buses from Salamanca to Leon
http://www.guia-digital.com/salamanca/turismo_en/transporte_buses_en.cfm

I think the name of the bus co. bus Empresas Vivas but I can't find my notes. I'll keep looking.
Now, I'm not sure if there is a bus from Leon to Segovia. I didn't go to Segovia. From Segovia to Madrid is www.lasepulvedana.es
What I did last year when I couldn't find out what bus co. to contact was to e-mail the hotel of my originating city and ask them. They were always able to tell me.

cruiseluv,
Thanks again for the information.

Did you need reservations on the buses in advance, or is it fairly safe to wait until we're there to get the tickets?

I remember trying to make reservations online on auto-res for Salamanca but for some reason I couldn't, the system wouldn't work . It was a good thing that I got to the bus depot early( 30 mins-40 mins before departure) because the bus left full. It would not have been a amjor problem( other than waiting for another hour) since buses to Salamanca( and I think to Avila) are frequent.
I remember the bus company that went from Salamanca to Leon would not accept reservations.

With the bus co. Alsa which I used to go from Leon to Oviedo and other points north I made reservations in advance. A couple of times the buses went full so I was happy to have made the reservations.
Have you gotten your hotel reservations confirmed?

cruiseluv,
Funny you should ask. I just confirmed with the Paradors online, but am a bit confused. Have you purchased one of these cards.

Am going to post re my confusion or call Luis at Petrabax and get it cleared up.

Thanks again for the help.

Artlover,
Are you referring to the 5 nights card? I bought it in the first Parador we stayed. You don't have to buy it online( unless something has changed)