Help with 19 day Spain & Portugal Itinerary for solo traveler

To me, the most expendable destination on your proposed itinerary is Valencia (which is why I haven't been there yet, but that does call into question the validity of my opinion). I consider Toledo unmissable for a traveler with as much time as you have. It needs at least a full day; I spent 3 nights there but acknowledge that it is not lively in the evening.

Cuenca, aside from the medieval hill district, has two good modern-art museums. It is a charming place. Note, though, that it is practical as a day-trip from Madrid only via AVE train. That ticket will be painfully costly if you don't buy the ticket early. Check the fare on Renfe.com right away so you'll know whether that is a practical destination. If you decide to go, don't dally in buying the ticket once you have your timing pinned down.

Segovia is another good day-trip from Madrid. There is some price variation in rail fares to Segovia but nothing like you'll run into with Cuenca.

Fares to Toledo do not change, but those trains do occasionally sell out, so it's smart to buy the ticket a few days in advance if you can.

In Spain round-trip fares are often about the same price as one-way.

I'd definitely add the Valencia time to Barcelona. Not only does it have enough sights for 10 days, but the most popular ones need pre-purchased (usually timed) tickets, which makes cramming a lot of sights into one day problematic. Good side-trips from Barcelona include Girona (medieval center, walkable wall, two cathedrals, good art museum), Figueres (Dali Theatre and Museum), Cadaques (picturesque former fishing village, accessible from Figueres by bus), and Montserrat. There are many others, but the city itself will fill a lot of time

Perhaps I'm not up to date on train schedules from Sevilla to Granada, but I thought it took about 3-1/2 hours between the two cities. If you take a "noon train", will you arrive in Granada with ample time to visit the Alhambra?

Two and a half days in Barcelona seems inadequate to me, but I'm a big fan of Gaudi and the Modernista buildings and spent a great deal of time at these venues.

Having just been to Portugal, I would say, skip Sintra altogether, crowded, touristy, almost Disney sweet. I'm sorry I wasted a day there.

I enjoyed Sintra a lot and found Obidos (though picturesque) more touristy, but Europe was less crowded then. Still, there could be a huge difference between August and October.

Thank you to everyone for your responses!

@acraven I'll look into the AVE tickets to Cuenca because I'm very interested in visiting and want to buy them at a reasonable price. Thanks for the tip!

@Jon You're right about the long train ride to Granada. I am planning on visiting the Alhambra the day after I arrive. I have a new itinerary that will include more days in Barcelona (see below)

@pameladrake I am actually intrigued by the disney-like image of Sintra, but I wouldn't want to visit Sintra if it's too crowded. Like @acraven said, it might be less crowded in October than in the summer.

Here's a revised itinerary:
Day 1 - fly from the US to Lisbon, Portugal

Day 2 - Arrive in Lisbon in the afternoon

Day 3 - Lisbon

Day 4 - Lisbon

Day 5 - Lisbon (maybe day trip to Sintra)

Day 6 - early morning flight to Sevilla, Spain

Day 7 - Sevilla

Day 8 - Sevilla

Day 9 - Sevilla

Day 10 - early morning train to Granada

Day 11 - Granada (spend day visiting the Alhambra)

Day 12 - Granada (maybe day trip to Cordoba)

Day 13 - morning train to Madrid

Day 14 - Madrid

Day 15 - Madrid

Day 16 - Madrid (day trip to Toledo or Cuenca)

Day 17 - morning train to Barcelona

Day 18 - Barcelona

Day 19 - Barcelona

Day 20 - Barcelona

Day 21 - Barcelona

Day 22 - return flight from Barcelona

A few more questions:
Is it worth doing a day trip to Cordoba from Granada? The train (not high speed) will be 2.5 hours each way.

One of my travel days lands on the National day of Spain (Fiesta Nacional de España). Would it be advisable to travel on the morning of this holiday? I've read contradictory info on travel forums about whether the trains run on this holiday.

No, with your itinerary I wouldn't do Cordoba as a day-trip from Granada. You have two better options:

• Cordoba as a day-trip from Seville (much less travel time, and the usual choice if not overnighting)
• Cordoba between Granada and Madrid (storing luggage in Cordoba, or overnight stay). Less total travel time.

I think the new schedule looks good.

First, look into bus schedules to/from Granada. The journey time is about the same. In Granada, the train station is on the edge of the old city center, the bus station is about a kilometer or so farther out. If you're planning on taking a taxi it doesn't much matter. Note that the trains only go as far as Antequera. From there to Granada, the train company, Renfe, provides a shuttle bus that goes to the train station. The transfer is seamless, but it does mean a little extra loading/unloading luggage.

There's no sense to a day trip from Granada to Cordoba. Just take the train or bus (the train and bus stations in Cordoba are across the street from each other) to Cordoba and either spend a night or two or leave your bags in storage at the bus station, spend the day seeing Cordoba and continue on to Madrid in the evening. Note: if you need to use the bathroom, use the ones in the train station (clean and modern), not the ones (yuck) in the bus station.

I think a day and a half in Granada is enough. And Cordoba is my favorite Spanish city. It's lovely in the evenings, very quiet and romantic. There's a good English walking tour in the evenings (book through the TI there).

I also think that Madrid is the least interesting city I've been to in Spain - except for the 3 outstanding art museums. If you love European painting, you'll want 2 full days in the city for that. Otherwise you can see the highlights in 1-1.5 days or even skip it. Toledo is lovely and much better as an overnight (or even 2 nights) visit. Toledo is on a spur line. You'll have to take the fast commuter train there and back from Madrid's Atocha station. You can easily transfer trains, though you need to allow at least 30 minutes transfer time - it's a big station.

I'm guessing that your holiday is October 12 and it's a Friday so think "holiday weekend". The trains may be more crowded on Thursday afternoon/evening and Sunday. Except for trains to Toledo, I haven't noticed any differences between weekday and weekend schedules for the fast trains. BTW tickets should be on sale already for the dates of your trip - there are big savings if you buy no refund/no change tickets now.