Spain in July 2017 with teenagers - Madrid, Barcelona and where else?

Pamplona might be fun if the kids are into it, but they might not like that things don't end well for the bulls... Also, I'd expect accommodations fill up at that time, so that might drive your decision.

You could spend 5 days in each city but take some daytrips. Toledo, 30 minutes outside Madrid is probably the most famous and popular. Segovia has a dramatic Roman aqueduct and is a nice hill town. El Escorial might bore most teens.

Outside Barcelona is Tarragona, a Roman city with an impressive coloseum right along the coast and a small but nice museum. Plus a stop at beach town Sitges is easy to add to that daytrip. Girona is a lovely small city and can be combined with the Dali Museum in Figueres (that will blow their minds). If they are outdoorsy, hiking at Montserrat is an option.

I have not been to the Basque region but my impression is that it might not offer much to excite teens. Other who have been can prove me wrong...

If you settle in for 5 nights each, you could look into an AirBnB and let the kids get used to a neighborhood. That also might reduce the stress of moving around and let them chill some.

Add Toledo and Segovia day trips. But it is hilly warm and sunny beware

I've been to Madrid and Barcelona and feel you could probably cut a night from each in order to spend more time in northern Spain - where I've not visited. I'd give the Festival a go for sure and also San Sebastian. Whatever you choose you'll have a great time.

I'm not good at picking destinations for teenagers (or younger children); these are just my suggestions from the adult perspective:

Basque Country:

• Both San Sebastian and Bilbao have picturesque historic districts. Bilbao's is larger and not particularly near the Guggenheim so gets overlooked by many travelers. I prefer it. SS's beach is spectacular, but the weather may not cooperate (but if you get cool weather, you'll be grateful). The Guggenheim offers an English-language tour once a day (around mid-day in 2016); book at the information desk when you arrive, ask what part of the museum the tour will cover (was ground floor when I visited), and visit other parts of the museum while waiting for the tour to begin.

• The border town of Hondarribia has both a colorful fishermen's quarter (restaurant central) and an upper medieval district. Buses make the run from the lovely Placa Gipuzkoa in SS.

• Three smaller coastal towns I visited on the other side (W) of SS: Zumaia, Getaria and Zarautz. All three can be hit in one day via public transportation (combination of bus and train), or one can walk between Getaria and Zarautz in about an hour (3 miles).

• The inland city of Vitoria-Gasteiz has a large hilltop historic district. It's very atmospheric and not very touristy. Last year one could take an English-language tour of the cathedral, which is being restored and is not otherwise open to the public. There are a couple of art museums and a playing-card museum.

Madrid offers tremendous side-trip possibilities: Toledo (my favorite, and an opportunity to see some mudejar architecture without going to Andalucía), Segovia (pretty historic area in addition to the aqueduct), and Cuenca (hanging houses along a ravine and two good modern-art museums) are the big 3 for me. I haven't been to El Escorial and was underwhelmed by Avila. Note that Cuenca is financially viable only if you book the AVE tickets far in advance.

From Barcelona, Montserrat might be especially good because of the opportunity for outdoor walks. And the Dali Theatre-Museum in Figueres seems wacky enough to appeal to all ages. Others can suggest good beach breaks in the area.

Check now for hotel rates in Pamplona during the festival. It may be difficult to find anything at all. I used Pamplona as a stop of convenience last year and found it not a particularly exciting city outside festival time (which is pretty much what every guidebook I've seen says), but it has an historic area, and I did enjoy the life-size running of the bulls statue.

I wouldn't venture off your Madrid - Barcelona path, if it's just one/two nights you are looking at. Zaragoza makes an easy stop between the two.
Otherwise, I would just look at more day trips from both big cities.
Madrid - Toledo, Segovia, Avila, El Escorial
Barcelona - Tarragona, Girona, Figueres, Montserrat

Thanks for your suggestions everyone! Based on the input here and from others, we've come up with an itinerary and would love thoughts and input.

Madrid (2 days)
Toledo (2 days) with day trip to Segovia?
Pamplona (2 days) - we decided to go for it even though it may be crazy with the Festival. We're not really Times Square on New Year's people, but it seems like a once in a lifetime opportunity!
San Sebastian (3 days) with day trip to Bilbao
Barcelona (5 days) day trip to Figueres and ?
Madrid (1 day)

Here's a little more about us and how we like to travel:

Our 16 year old is a girl - she's likes art and shopping, our 14 year old is a boy - he likes soccer, sports and more active sightseeing. We all like the outdoors and hiking and are pretty adventurous eaters. I love to spend hours in a new city, walking through the neighborhoods and getting to know the city on foot, and stopping to eat and drink along the way. We're not big group guided tour people, although I could see doing a food tour (maybe a wine tour depending on the kids). We all also love the beach.

My husband and I have been to Europe before. I spent 6 months in Paris in college and my husband spent 6 months in Athens. We both traveled around then and have been back to Europe since - to France and Italy. We really loved our time exploring smaller towns as much if not more than big cities - loved Siena more than Rome (which was so crowded!), for example. We are planning on renting a car for part if not all of the trip.

Would love to hear any suggestions or recommendations you have.

Thanks!

From a scheduling standpoint it is often recommended that the departure city be left until the end of the trip so that you don't waste a substantial part of the last day rushing back. Your case is an ideal one for that plan, because you can easily head to Toledo by train (or even by bus in a pinch) on your day of arrival. It appears that the fare will not increase if you buy at the last minute, so you don't need to guess what would be a viable departure time from Madrid. I think you may save a substantial amount of money by buying round-trip tickets to Toledo rather than two one-way tickets. A further advantage of this plan is that it's a way to utilize part of your (probably jetlagged) first day on a necessary relocation,

Your side-trip to Segovia should be made from Madrid rather than from Toledo, for reasons of geography.

Pamplona gets booked up for the festival. Look for lodgings now. Be careful about cancellation policies. You may encounter minimum-stay requirements (pure speculation on my part). If you end up taking the train, I imagine you need to buy the tickets well in advance, too (still guessing).

All the possible side-trips from Barcelona mentioned up-thread can be taken on the spur of the moment (just check bus/train schedules in advance), so you can wait to see how much you want to do in Barcelona before making a decision. The same is true of the Madrid-to-Segovia trip. As I mentioned previously, Cuenca is a non-starter if you book last-minute AVE tickets, because of their cost.

Check ViaMichelin for driving times and estimates of fuel/toll costs so you can do a proper comparison to train fares. I would anticipate quite substantial parking costs in Madrid and Barcelona; I'm not sure about the other cities.

With two weeks available to you and two large cities plus Pamplona already planned, I don't see you doing a lot of wandering around through small towns, and the train will often get you from place to place faster than a car. Fares for four people for your Madrid-Pamplona-Barcelona travel legs could be either a bargain or substantial, depending on when you buy tickets.

Check rail schedules and prices on the Renfe website. Stations for the three large cities are:

Madrid-Puerta de Atocha
Pamplona/Iruna
Barcelona-Sants

Segovia from Toledo is not really an efficient routing. I would flip things a bit. Oh, and think in terms of nights.

Arrive Madrid. Direct to Segovia (1 night)
San Sebastian (3 nights) with day trip to Bilbao
Pamplona (2 nights)
Barcelona (5 nights) with day trip to Figueres and Girona
Toledo (2 nights)
Madrid (2 nights)