I have been to both, and I feel that there's more to see/do in Toledo than Segovia. However, if a lot of sites are closed on Monday in Toledo, then I'm not sure if it's "worth" your visit. Is it possible you go on a different day?

Here's a link to my day trip to Toledo:
http://www.fodors.com/community/europe/yks-12-days-in-spain-by-herself-trip-report.cfm#comment-1545443

And link to my day trip to Segovia:
http://www.fodors.com/community/europe/yks-12-days-in-spain-by-herself-trip-report.cfm#comment-1545475

I'm sure Maribel will chime in. We faced the same decision for our trip, and decided to head north to Segovia for its less-touristy feel and charm. We'll save Toledo or a future trip. You should read her guides for both cities and decide for yourself.

P.S. www.maribelsguides.com iris1745/dick

Thank you! This will be helpful. I'm kicking myself for not taking some extra days off in order to lengthen our trip. (I'm a teacher--spring break.) Our plan is 3 nights in Madrid, visiting our daughter, 2 nights in Granada, 2 nights in Sevilla, then back to Madrid for a day before returning home. We have to do Madrid at the front end of our trip, arriving on Saturday, because that's when our daughter will be there.

I will double check what must-sees are closed on Monday and try to make a decision. (Or shorten Granada or Sevilla?)

I'm looking at these wonderful Maribel guides, and I have some transportation questions. (Hope it's okay to ask here.) We usually like to rent a car in Europe so we can get off the beaten path, and don't have to worry too much about timetables and hauling luggage. This time the trains and buses seem to go where we're going, so we thought we would give them a try. Does that make sense?

It looks like our best bet is the high speed train for a day trip to Toledo or Segovia. (Leaning towards Segovia--I just love the looks of the place!) Then from Madrid to Granada, the ALSA bus is better than a train? It looks like that is also true for Granada to Sevilla, although when we return to Madrid we would take the AVE from Sevilla. If that's the case, I'll have to convince my husband, who is not enthusiastic about buses.

Thank you so much; I have already been helped a lot!

Hi mhutch196,
The Toledo vs Segovia question must be one of the most frequent asked questions here about Spain itineraries. It's just a hard one to answer definitively because it depends on what most appeals to you personally.

Toledo is more "labor intensive" in the sense that there is more to see, primarily great art (in its cathedral, the synagoges, its museums) so if you're not a big religious art lover (El Greco, especially), you might enjoy less touristed Segovia more. I do love Segovia and personally favor it over Toledo because it just feels more real, more charming and less touristed trodden to me. But I've been to both many times. I respect and admire Toledo greatly for its art treasures and its 3 culture/religious history (Jewish, Islamic, Christian), its incredible setting. But I do enjoy it more with an overnight, after the tourist buses have left, the souvenir shops have closed. For me Toledo then becomes enchanting (and slightly mysterious) at night.

To reach Toledo or Segovia, the easiest way now is on the high speed AVANT trains. The train to Toledo departs from Madrid's Atocha station, while the Segovia train departs from Chamartín in the northern section of the city and goes to the new high speed station at Guiomar, 4 kms from the city. Then you take the bus that meets the trains, and it drops you off directly in front of the aqueduct.

Both Madrid train stations are connected via the Cercanías (commuter) underground line.

From Madrid to Granada, you can take the Altaria train, departing at 9:05, arriving at 13:32, the comfortable, modern clean Alsa bus with Supra service-direct, departing at 8 from the Estación Sur de Autobuses (Méndez Alvaro metro stop below) and arriving at 12:25 or fly non stop on Iberia (buying a r.t., which is cheaper than one way). I see one way Iberia fares for a round trip ticket as cheap as 54 euros, but I didn't check your specific dates.

The advantage of the bus from Granada to Sevilla is that there are more daily departures.
Some folks are reluctant about bus service, thinking that the experience would be like an American Greyhound, but Spanish bus service is so much better and nicer.

I think the most economical from Madrid to Granada will be the bus or train.

I rechecked Iberia for flights down on March 31 with a return April 15 (realizing that you won't need the return ticket). I get a r.t. fare of 86-95 euros, the cheaper being for the 8:05 am flight rather than the 11:50 am. A one way ticket would cost 148.