14 Day Spain Itinerary (Fly Into Madrid, out of Barcelona)

In to one and out of the other - I don't think it really makes much difference which one, the idea is primarily to not have to double-back and depart from your arrival city, since there's generally no good reason to do that, and Barcelona is distant from "the rest of Spain" (insofar as most major destinations for foreign tourists).

How many days do you really have, not counting your arrival or departure days? With 12 - 14 days you should be able to cover a good bunch of ground. October is not a bad time to go - the summer heat (which can be oppressive in parts of Spain if you're not used to it) and the worst of the summer crowds won't be an issue. The flip side of that is somewhat shorter days and more variable weather. All that said, I've been a couple times in October and loved it.

There's plenty of things to do and places to see. Suggest you start with Rick's Spain books, also look at his tours - peeking at the tour itinerary can be a good way to start, and can give you suggestions for the most popular (if not necessarily the "best") attractions - they include the places that are crowd-pleasers so you can't go wrong hitting most of those. Just keep in mind that unless you are a pretty efficient/experienced traveler, you may be hard-pressed to maintain the same pace as one of the tours. Having all the arrangements made for you and being driven around allows you to spend more of your time seeing and doing, and less on "logistics" (finding the hotel, the restaurant, etc.). Of course, some of us enjoy the logistics and often have great experiences as part of making it on our own.

We flew into Madrid (from Lisbon) and out of Barcelona (to Nice). I really don't think there's a lot of difference, except that, in our case, we would have had a few more flight options to Nice from Madrid.

Toledo is an easy day trip from Madrid and has a lot to see. My favourites were the cathedral (HUGE!), the museum with the El Greco paintings, and the little tourist train.

In Madrid, I loved the Palacio Real, the Prado, Retiro Park, the Reina Sofia, and just walking around the plazas and markets.

From Barcelona, a wonderful day trip is Montserrat. I loved it. It is one of my favourite sights, ever.

In Barcelona, the Gaudi sights were the most memorable for us, especially the Sagrada Familia. They were also the busiest. I also liked the Barri Gotic, especially the Cathedral with the geese in the cloisters. http://barcelona.de/en/barcelona-cathedral-la-seu.html

I agree with David - starting or ending in Barcelona is equal. The big mistake people make is booking a roundtrip ticket to Madrid; since that's in the center of the country, it's then hard to organize an itinerary that avoids backtracking and crisscrossing, which in turn wastes time.

It's easiest to start thinking of Spain as a set of regions, not only for logistics, but also because of the intense differences between them. With 2 weeks, pick 2 or 3 regions to see. Some choices include Catalunya (around Barcelona), Castille (around Madrid), Andalucia (around Seville and Granada), Basque Country (around Bilbao and San Sebastian) and Galicia (around Santiago de Campostela and A Coruña). These are the most high-profile for first time visitors, but there's more to the country, of course.

Start with Rick's Spain book and videos https://www.ricksteves.com/watch-read-listen/video/tv-show (scroll down and click Spain) to see what appeals, and do take weather into account. At the time you're going, large parts of the country should have nice weather, and it should be a good time to go to Andalucia, which can be intensely hot closer to summertime. However, I don't know what the weather's like then in Basque Country or Galicia; these areas famously get lots of rain in certain seasons (the rain in Spain does NOT stay mainly in the plain - that part's drier).

I must respectfully disagree with one thing BB said: Toledo as a day trip. Listen: Toldeo can be wonderful, or a miserable mess overflowing with crowds of tourists. The best way to ensure Toledo is a miserable lowpoint to your trip is to - get ready - do it as a day trip from Madrid. Because EVERYBODY does it as a day trip from Madrid. It's close, it's easy. So - surprise! around 10 am every day, the train doors open, the busses roll up, and disgorge 10,000 day-trippers, where they clog the streets shoulder-to-shoulder until 4 pm, then the human tide recedes, leaving the town delightfully empty and magical. Most people make this mistake, and it's easy to understand why: they have booked a hotel in Madrid for four or five days or some stretch, Toledo is a short train/bus ride away, and it's easy enough to get there. The problem is that everyone does that, and that (at least to me) completely ruins the experience. If you arrive mid-afternoon, you will see the packed streets, but you will then see the crowds disappear, leaving a beautiful, intact, charming medieval hill city, all to you and just a relative handful of smart visitors to enjoy for the late afternoon hours and into the night. Sleep in the old center. Get up early and go out and enjoy the city again for a few hours. Because around 10 am, the hoards will be back. That's when you should make your getaway. The downside of this plan? You have to pay for a night's lodging in Toledo (not excessively expensive, but a minor splurge compared to Madrid where there's oodles of competition and lower prices). The benefit is that you get the city at its best, instead of its worst.

Couple years ago, family members were going to Spain. They had Toledo on their list. I gave them the advice above, and implored them to be smart and spend the night in Toledo. Yes, I explained, they would have to spend a few bucks more for the night spent in the old center, but for that they would get an experience that would be one of the highlights of their trip, rather than something they wished they had skipped. I stressed that it was well worth the small extra cost - how many times you gonna go to this corner of the world, I asked? They agreed, it would be a smart move.

After they came back i asked him about his family's trip to Spain. "Oh, Spain was great...well, most of it" Did you go to Toledo, and did you like it? "Oh, we all hated Toledo", he said. "It was miserable. It was so crowded, we just wanted to get out of there!" I asked if they had spent the night as I suggested. "Oh, no - we saved some money by doing it as a day trip - we all wished we had skipped it and gone somewhere else instead." D'oh!! (facepalm...). True story.

I'm sure some here will disagree. But in my experience, the places that are being loved-to-death by mega-crowds of tourists (Toledo...Mont St Michel...Carcasonne...with the current explosion of worldwide travel, there's a long list), these places are best in the early and late hours, and it's best to skip them in the middle of the day. It's worth a few bucks more to sleep there and enjoy them when you have them more or less to yourself. Just my 4 cents. Good luck.

I agree with David in terms of spending a couple of nights in Toledo to fully experience it's beauty.
My mom & I had visited Toledo as a day trip years ago, but last October we spent 5 wonderful nights there & enjoyed this amazing medieval city.
Córdoba is another beautiful city that most people visit as a day trip from Sevilla. IMO, it also deserves at least a few nights to explore & enjoy.

Edit: If you plan to visit Granada, make sure you book your Alhambra tickets way in advance.

Once you figure out your itinerary, you can save money by booking your train tickets in advance!

You may consider visiting Sevilla too! :-)

We recently did a 14 day trip in Spain starting in Madrid and ending in Barcelona and had a fabulous time! Our agenda, of course, reflected our own interests but since it worked so well for us I'm pasting it here as one example of what's possible. We packed a lot in, but we're pretty energetic and the schedule fit us well.

Day 0: arrive Madrid in the evening, explore Sol
Day 1: Madrid: am El Escorial, pm Madrid (Renia Sofia, the Prado, Parque Retiro)
Day 2: Madrid: had planned to go to Toledo but enjoyed Madrid so much we decided to spend a second day exploring (Museo Cerralbo, back to the Prado, etc.)
Day 3: Madrid to Cordoba on AVE train in the morning, afternoon/evening exploring Cordoba
Day 4: Cordoba to Granada: am more exploring in Cordoba, afternoon bus to Granada, pm Granada (Royal Chapel and evening Alhambra tour)
Day 5: Granada to Sevilla: am Alhambra and Generalife, afternoon bus to Seville, pm explore Seville
Day 6: Sevilla (Royal Alcazar, Palace of the Countess of Lebrija, Palacio de las Dueñas, Archivo General de Indias, and pm Flamenco show, sunset carriage ride in the park)
Day 7: Sevilla to Madrid: am Cathedral and Basilica de la Macarena in Seville, afternoon AVE to Madrid, late afternoon tour of Royal Palace in Madrid
Day 8: Madrid to Costa Brava: am AVE to Barcelona, walk in Barcelona, short bus to our Costa Brava town, pm walks along old city and beach
Day 9: Costa Brava
Day 10: Costa Brava to Barcelona: am swimming, early afternoon bus to Barcelona, pm tickets to Park Guell
Day 11: Barcelona: organized tour surrounding historic towns
Day 12: Barcelona: Sagrada Familia, Casa Pedrera, Palace of Music tour, evening train to Tarragona (we were going to spend the rest of our time in Barcelona but weren't really loving it like some people do)
Day 13: Tarragona: am exploring sites and wading in the sea, pm train to Barcelona and airport, late evening flight out of Spain

Day 1 Arrive Madrid (4)
Day 3 Day trip to Toledo
Day 5 Train to Sevilla (4)
Day 7 Day trip to Córdoba
Day 9 Train to Granada (2)
Day 11 Fly to Barcelona (4)
Day 15 Depart Barcelona

Personally, with 14 nights or days and Madrid and Barcelona as fixed points, I would skip Andalucia this time. It is in the complete opposite direction and not well connected to Barcelona. So you'll either be adding a flight or backtracking by train. And it will cut down on seeing the incredible regions around Madrid and Barcelona. If you did want to add a 3rd major city, consider Valencia. It's well connected by AVE from Madrid and then to Barcelona and is a nice city to spend a couple of days in. And you'll see a completely different kind of Spain there from the other two cities.

So you could spend 5-6 days in Madrid/region and Barcelona/region and a couple days in Valencia and really see some amazing places without it being a whirlwind.

You have selected a wonderful time of year to visit Spain and allocated ample time to take deep dives into exploring two distinctly separate regions and cultures.
First, book apartments for your accomodations. Apartments offer another avenue to experience the culture, added room space, a kitchen, sometimes a clothes washer and often a better value. Dive deep and do research on recommendations paying special attention to reviews. in Madrid we stay in the Latina district which offers excellent accessibility to old town Madrid, but is outside of the main fray of tourists. We suggest seeking an apartment on a higher floor which has a terrace as having a glass of wine and cheese/jamon is an excellent way to end the day or to begin the morning with coffee. The higher elevation of Madrid offers slightly milder temps so you may not need a/c.
We recommend 4/5 nights in Madrid including time spent on day trips. Do your research and select destinations suiting your taste. We do recommend taking a picnic to Retireo Parc.
Madrid and Barcelona offer wonderful subway systems which are ez to use.
We advocate taking the AVE to Barcelona during day light hours as the views are interesting. Second class service is all you need. Allow some esrly arrival time at the Madrid train station as it is a wondeful place to explore.
Barcelona offers a huge menu of opportunities inside the tourist zones, exploring the city and excellent day trips offering a variety of interests. It is due to the size of the menu we suggest spending the remainder of your time in Barcelona. Again, book an apartment. In Barcelona we tend to seek apartments offering bedrooms with a view to the interior courtyards as these rooms tend to be quieter. We have stayed in a variety of locations in Barcelona and been pleased with the offerings found in each neighborhood. We suggest planning at lease two day trips due to the ez of travel via subway and train and the wonderful opporunitues. Our personal must see visit is to the palau of academy of music. This is a music hall of fantastic architecture and offers live concerts. Take the time to attend a concert and again add a different slice of cresting memories to your journey.
Enjoy!

With so little time you need to make choices and prioritize. There is so much to see in Spain. The top of my list would be the Mezquita
https://janettravels.wordpress.com/2013/09/27/the-mezquita-at-least-the-catholics-had-the-good-sense-not-to-destroy-it-when-they-desecrated-it/
And after that either the Alhambra or the Alcazar in Seville. WE also loved spending a couple of nights in Ronda to have a brief 'white town' experience, but that might be lower on the list given the time constraints.
https://janettravels.wordpress.com/2013/09/15/ronda-the-most-romantic-town-in-spain/
The Sagrada Familia is of course the top of the list in Barcelona. and the Prado in Madrid.

I would decide on the must sees and then try to spend 4 nights in Barcelona and Madrid and then choose among other priorities. You could do Cordoba and the Mezquita as a day trip from Madrid. We like to balance big cities with smaller towns hence Ronda and Cordoba.