Help!! Please share your thoughts on my Spain itinerary...and to Sevilla or not to Sevilla?!

Definitely cut Madrid. I LOVED Andalusia. Sevilla was my favorite of the cities. So much to do and everything is charming. I also see Cordoba is not on your list. Cordoba was my 2nd favorite of the cities. If you were to ask me, I'd drop a night in Malaga, add it to Sevilla and take a day trip to Cordoba with that day. Honestly, I think Cordoba deserves 2-3 nights, but many do it on a day trip.

Thank you, Jules. Dropping Madrid is definitely an option. And I was looking at adding Cordoba...maybe Cuenca to Cordoba to Sevilla to Granada to Malaga. Except that I dropped 1 town and added another!

The whole of this itinerary seems pretty fast-paced. As it is you'll get to see some, but not all, of the highlights in each place, and certainly not have a chance to linger, stroll, explore, savor... If you haven't bought tickets, I'd suggest going back to the drawing board and visiting Italy or Spain, saving the other for a future trip.

Spain or Italy, not both.
Sevilla should be a priority.

I agree with Scudder and Suki. This is an extremely fast-paced trip. You will see a lot of trains and train stations. There is no time for relaxation and just simply wandering and exploring. Unless you consider riding the trains relaxing. If you keep your current itinerary, I think you will come away feeling not only exhausted but very frustrated.

Choose just one country for this trip - Italy or Spain. Because you are spending more time in Spain, it looks like Spain is calling out to you more than Italy. Have you created a spreadsheet with destinations and number of nights? Remember, 2 nights in one place essentially gives you one full day and maybe half of another day. This is how your current itinerary looks:

Rome - a couple of nights (so 2 or 3 nights?) - Rome is a huge city with so many historical and cultural sites and neighborhoods to explore. We spent a whole week in Rome many years ago. You need at least 4 or 5 nights. And you need time to get over jetlag in Rome.
Florence - couple of nights
Barcelona - 3 nights - really needs minimum of 5 nights to do it justice
Drive from Barcelona to Valencia - spending 2 nights somewhere along the way
Valencia - 2 nights
Cuenca - 1 night
Madrid - 2 nights - I think Madrid deserves 4 nights especially if you love art. Madrid has some outstanding art museums.
Seville - 2 nights
Granada - 2 nights
Malaga - 2 nights

Looks like this is filled with 2 and 3 night stays and you will be exhausted, and I think you will be very frustrated because you won't have a lot of time to sightsee and relax and savor the places.

Drop Italy and make this an all-Spain trip. You will be so much happier.

This could be a possible itinerary:
Barcelona - 5 nights
Roadtrip to Valencia - 2 nights
Valencia - 2 nights
Cuenca - 1 or 2 nights (haven't been there so don't really know if you need 2 nights). Keep in mind a one-night stay gives you half of one day and perhaps half of another day.
Madrid - 4 nights
Seville - 4 nights
Cordoba - 2 nights
Granada - 2 nights
Malaga - 2 nights

This is more than 21 days so something has to give. If you aren't art museum fans, then drop Madrid. Or drop the roadtrip to Valencia and drop Valencia. Haven't been there but you can't include all these places in Spain even with dropping Italy.

You also need to reserve your Alhambra tickets ASAP!

What Suki wrote.
Slow down. Enjoy life.

Too many stops, I think. Madrid is "out of the way" a bit, given the rest of the itinerary. Maybe drop Italy, keep Madrid? Or keep Italy and drop Madrid.

Also, check your train and other transportation times. That's a lot of driving/traveling, and it will eat up more time than you think.

Enjoy it! Both countries are amazing.

I agree that you’re trying to fit too much in. Between the crowds in Europe right now and the general pace of life in Italy and Spain, I think it pays not to bite off too much.

I agree to drop Madrid - it was my least favourite city on my Spain trip, Sevilla, Granada and Cordoba were much more enjoyable. I spent 3 nights in Sevilla, 2 nights in Granada and an afternoon/evening in Cordoba, and this was plenty of time to see the main sites.

Curious as to why you were drawn to Valencia? There is nothing wrong with it, all of Spain, is quite fabulous, but some places have more history and charm than others. With limited time, I'm not sure I'd spend it in Valencia and Madrid. Yes, those cities are beautiful. Yes, Madrid has world class art museum, but in terms of history and culture and local flavor, I'd put the other cities higher on the list.

I've been using and participating on this forum for quite a while. When we first started traveling to Europe about 10 years, ago, we weren't retired, so we had limited time. I tended to be conflicted about the advice I was getting. I felt like if I didn't spend a week in Paris, or other major cities, we were just doing it wrong. True, you don't want to spend your vacation on planes, trains and buses, but you don't have the time to fully savor and take in a city like many on the forum do. The key is finding a balance. Now that we are retired, we do travel slower and for longer periods of time, but we still travel faster than most on the forum. I'm not saying you are getting bad advice, you are not, I'm just saying I understand that you have places to see! Absolutely, use the amazing advice people on the forum have to offer, but also spend some time on google maps to see how long it will take to get places, make lists of objectives for each city. This will give you an idea of what will work for you.

It might also be helpful to say how many times you've been to Europe. If it's a few, then we know that you have a travel-style that you are comfortable with. Since transportation is a little more difficult in Spain than in Italy (or Germany), it's particularly hard to justify so many hotel/city changes. Are you flying home from Madrid? How did you select places like Malaga and Valencia, yet (tenatively, I mean) leave out Granada?

It's worth noting that Madrid has a few same-day excursions to consider. I rather like Madrid, but I grew up in a big city. Are you planning on air-conditioned accommodations? In September - Andalusia, I would.

WAY too many places for such short visits. Two days in Rome is ridiculous. You could do a week in Rome and not see it all.

You seem to have about 14 days in Spain,
Recommend 3 nights minimum in Barcelona. Not sure that I would spend all that time wandering to Valencia.

My favorite cities in Spain are
Seville
Toledo
Barcelona
Granada
Segovia
Salamanca (too far away for your to go there).

Madrid is nice, but mainly to go to the wonderful Prado Art Museum. However, it has the Royal Palace and is close to Toledo and Segovia that can be done on day trips from Madrid by rail.

I was not impressed with Malaga, but Rhonda is near there and good. Granada is a definite to see. All these place would exceed Valencia in interest. Just my opinion.