July 23 to August 4, Madrid and Basque Country

All very worthwhile destinations. Check projected driving times on ViaMichelin.com to help with the flight decision. I'd consider flying into Bilbao and out of Madrid.

Other places I liked in the Basque Country included Vitoria-Gasteiz, Hondarribia, Bermeo and Zarautz/Getaria/Zumaia. Bilbao has more to see than San Sebaztian, but the beach at SS is magnificent.

You'll need to remain flexible about the beach goal. On any given day the weather may not cooperate.

Thanks acraven. Times don't look too bad, about 1:30 to 2:30 from site to site. Is it better to have a place as a "base" and make day trips from there (I know crossing to France is recommended on Rick Steve's book), or just drive and stop for the night as we make our way?

globulin, we will be there at the same time in the same places. I think you'll find that there are SO many worthwhile stops, its hard to select the few you will visit this time. Yes you can return a car at a different place than you rented (we are doing this also). The "open jaw" flight you describe is certainly possible. Go to google flights and search under "multi city". I cant say whether it will be cheaper one way or another. It really depends on your point of origin, among others. Google flights (or Sky scanner) will allow you to see prices and options and then you can proceed). So how many days do you have on the ground? 11 days? So if you have 2 in Madrid, that leaves 2 days, approximately, everywhere else. Sounds about right. So you would drive Madrid-Segovia-Burgos-San Seb-Bilbao, and take a bus to Bilbao from SS for the flight? Your beach time could be had in SS, as you won't be on the coast much anywhere else. Im not sure what else to add. PM me if you have specific questions. We will be in N. Spain with our three teens for 3 weeks, so I did a lot of homework ;) Best,
Jessica

Hello, I think with 12 nights available one can make a nice road trip. Taking into consideration your last stop would be Bilbao, here would be my two sample itineraries recommendations:

Option 1 "The Roof of Aragón"
fly in to Madrid
Madrid (2 nights)
AVE Train to
Zaragoza (2 nights) rent car here
Drive north to
Huesca (1 night) explore Pyrenees
Continue north & make a stop at Loarre Castle
Jaca (2 night) explore the Pyrenees
Turn west & make a stop at Sos del Rey Católico
Olite (1 night) stay at Olite Castle Parador
drive north to
San Sebastian (2 nights)
drive west along coastal road to
Bilbao (2 nights)
fly out of Bilbao

or

Option 2 "Old Castilla"
fly in to Madrid
Madrid (2 nights) rent car
drive north to
Segovia (2 nights) day trip to Salamanca
drive north & make a stop at Coca Castle
Burgos (2 nights) day trip to Monasterio de Santo Domingo de Silos
drive north-east to
Vitoria-Gasteiz (2 nights) day trip to Laguardia
continue north-east to
San Sebastian (2 nights)
drive west along coastal road to
Bilbao (2 nights)
fly out of Bilbao

Hope this helps :)

Of the places you mentioned, the only one with a Parador is Segovia. The closest to Madrid is Alcala de Henares. In the general vicinity of where you are going, there are Paradors in Hondarrbia, Santo Domingo de la Calzada, Santillana Del Mar, a couple in Picos de Europa. Olite, and Calahorra. There are more, but the ones I mentioned are the majority in the areas you’ll be traveling to. I wholeheartedly recommend Paradors.

Since I'm always dependent on public transportation and dislike changing hotels, I tend to stay at least 3 nights practically everywhere and make a lot of day-trips, but I'm pretty careful to select day-trip destinations that can be seen pretty comprehensively in the number of hours I'll have after allowing for the out-and-back transportation. (I wouldn't want to day-trip to Bilbao.)

Having a rental car would change things, and I would definitely have shorter stays, on average. I would not be happy with a vacation of only 1- and 2-night stops, however; I would never feel settled. I love the feeling I get when I check into a hotel room for a nice, long stay.

What do the kids like? Roman history, Medieval history, modern art, nature, etc.

Coming out of Madrid to see Segovia, you could stop at the parador en La Granja de San Ildefonso. Built by Louis XIV grandson, it is the Spanish Versailles

Or you could go up to parador de Lerma. This year Lerma is hosting the Edades del Hombre exhibition.
From Lerma if there is interest, you could follow the Way of El Cid. Covarrubias is a nice little town with an interesting history. If there are any Spaghetti Western fans they can follow the Good Bad and Ugly Route and visit Sad Hill Cemetery where the final duel was filmed.

From Lerma you could go up to Burgos. Santo Domingo de la Calzada has been mentioned, and I wouldn't usually recommend the visit, but this year is the 1000 birthday of the Saint and the town is celebrating big time. This weekend the Vatican Choir sang. During the whole year they will have an activities.

If Roman history is a bit more what you'd like after Segovia you could go to the parador in Siguenza (for me one of more impressive sights). From there you could go Medinaceli and visit the Roman ruins. Then up to Soria. There is a parador in Soria. And just outside of the town are the ruins of Numatia. It took the Romans 20 years to conquer the fortified town. From Soria you can drop down to Zaragoza to see the Roman sights there.

As for the part around the Basque country, if you like nature and a bit of relaxation, look at the Batzan Valley. The main town is Elizondo. The valley if full of hiking trails. At the top of the valley, along the board with France there are several caves you can visit, like Urdax and Zugarramurdi (where the last witch coven in Spain was stamped out) and in France, Sare.

Thank you so much to all of you for the very detailed and informative responses! I am getting deep into Rick Steves and your answers here tonight to set up an itinerary (I may return with a few more questions, I hope that's all right). My wife's family is originally from Abaltzisketa (1300 to 1910 or so), so we will likely try to make it there. Would anyone else suggest a different lodging option or has any hotel recommendations over or in addition to the Paradores?
Thanks again, very much!

Abaltzisketa is very near Idiazabal. If you like cheese you should visit the Idiazabal cheese visitor's center.

There are three tour options: Museum only 2.30€, Museum+Cheese tasting 3.40€ and Museum+Cheese+Wine is 4.50€

In Burgos, we stayed at the Abba Burgos Hotel. It’s about a five minutes walk from the cathedral. The last couple times we’ve been to Madrid we stayed at Hotel Europa. I’ve never stayed in Bilbao or San Sebastián.

While I can't speak about the driving portion, as I'll also be following this thread for a return trip to Basque Country, I can speak about the area around San Sebastian.

Northern Spain is noted for very good surf so, you're going to come across a beach culture that is more akin to what you'd see in American surf spots than what's typical in Europe. Surf boards, boggie boards, paddle boards are pretty common on the beach. Donostia-San Sebastian has two very iconic beaches which are right in the city itself so, nothing is too far. It can get crazy packed during the warmer months as many Spaniards from other parts of the country will also flocked there for heat relief. Nearby the small town of Zarautz I really liked and have it marked for a beach-trip when I return, very nice break there too!

Thanks again to all for great tips. This is what made our Italy and then our Slovenia and Croatia trips so memorable! We are "playing" more or less with the itinerary for Old Castilla posted above by Carlos. The pressing question is that we have one day less than that itinerary...so if you had to remove 1 day from it, what would that be?

fly in to Madrid
Madrid (2 nights) rent car
drive north to
Segovia (2 nights) day trip to Salamanca
drive north & make a stop at Coca Castle
Burgos (2 nights) day trip to Monasterio de Santo Domingo de Silos
drive north-east to
Vitoria-Gasteiz (2 nights) day trip to Laguardia
continue north-east to
San Sebastian (2 nights)
drive west along coastal road to
Bilbao (2 nights)
fly out of Bilbao

Finally, 1) Leaving Madrid (assuming earlier part of the morning) on the way to Segovia, what would be the best stops, while leaving enough time to walk around Segovia later in the day? El Escorial and Valley of the Fallen, or La Granja?
Or do the some of those combined with a day trip to Salamanca?
Speaking of, is it worth stopping in Avila on the way? Walking the walls? (we've done the walls in Dubrovnik and Montenegro, in case the reference helps to make comparisons. Rick Steves does not seem to believe it's worth walking the walls, rather, just a quick stop to see Avila).
Thanks again so very much!

I'm not a fan of Avila. I seldom pass up a walkable wall, and I didn't skip Avila's. My issue with the town was that there just wasn't much of anything else to see--and I can usually be happy, wandering around the historic part of town for a few hours. I found so much more of interest in Segovia, Salamanca, Burgos, Vitoria-Gasteiz, etc.

Some answers to your queries:

1. I would subtract one day from Burgos, I feel one can see the highlights of the town with 1 night. For me, Segovia has more options day-trip wise, which is why I gave it 2 nights to allow for a potential day trip to Salamanca, which is the quintessential Castilian town.

2. El Escorial will take up much of your limited time, better leave it for another trip to Madrid, and Valle de los Caídos is not where you want to go. I would instead recommend a stop at Ávila‎ to see her impressive walls and the Convent of Santa Teresa, before spending most of your day at Segovia.

Would there be a difference doing the trip the other way around? Air tickets are $400 cheaper flying into Bilbao and out of Madrid than the other way around. Would this have any real influence on the trip?

The only real difference would be you would have saved a lot of $$$.

In addition to saving money, it's probably easier as well. To get a flight back to the US that goes Bilbao-Madrid-US, the Bilbao flight probably leaves VERY early in the morning!

So, definitely start with Bilbao. It's a pretty easy place to get over jet lag, as it's largely walkable. If you don't want to walk, the easy, single-line, can't-get-lost-on-it tram connects almost everything of interest

Also, if you are still looking for hotels in Bilbao, I can heartily recommend Hotel Hesperia Bilbao, it has a great location, on the riverside park right across from the Guggenheim Museum, and also a very good breakfast.

Here is their website link:
http://www.hesperia.com/hoteles/hesperia-bilbao/

Thanks again to all of you! We keep getting tempted and moved the dates of our trip to July 26 to August 11, adding more days. We will start in Bilbao, like arriving around 5:00 at the airport, Saturday late afternoon. Stay two nights (or three) (thanks Carlos for the hotel tip!) and go to San Sebastián for three nights. Then Burgos by way of Vitoria, two nights, Segovia (two nights) and Madrid. However, having a few more days now, we may do two nights in Bilbao, visit Vitoria during the day (on the way to Burgos) and have an overnight in Toledo before heading back to Madrid. Or add Pamplona or more of Aragon instead of Toledo. So many choices! Thanks!