suggestion for a stop in between San Sebastian and Madrid (along a train route)

Not small, but Burgos or Logroño are nice for a night. Just south of Burgos is Lerma. It is much smaller, the Parador there is nice, and it’s on a train line.

Olite fits the bill! If you ever wanted to stay overnight in a storybook castle— this is your chance. You can stay at the Royal Palace for less than a hotel here at home.
There also are excellent restaurants in Olite serving the regions fine wines along with fine food.

Thank you so much, jaimeelsabio and Kenko! Olito and Lerma are now my top two choices. They look perfect for an overnight stop with relaxing strolls. We'll have been on the go for a week and a half at that point, so something small and manageable will be nice. And both Paradors look amazing. The one in Lerma is quite a bit more than the one in Olito, so that might be the deciding factor. Thanks again!

There’s absolutely nothing wrong with the Parador in Olite. It occupies part of the old castle. We spent a couple nights at it in 2022. In the photo our room was the one with the enclosed wrap-around balcony. The Royal Palace in Olite has been painstakingly restored and very much worth visiting. If you are into wine tasting, there are a couple bodegas within about a five minutes walk from the Parador.

There are not many restaurants in town. Of those, some are closed on one day while others closed on another, so you can’t be too picky about where you eat if you’re in town on one of those days.

That's great information, jaimeelsabio, thank you! We do love wine and were hoping to do some tasting. As for where to eat, we will take that into consideration. Speaking of which, if I may ask, did you opt for either the breakfast or half-board options at the Olite Parador? I'm trying to decide if it's worth the $$.

Hi Gayle, We faced the same dilemma after reserving a room at Olite’s Royal Palace. After studying the menu, it appeared that there wasn’t much advantage in committing to half-board in advance. We did have the excellent breakfast buffet at the Palace. We learned of a highly-recommended restaurant that is part of a hotel just 300 feet away from the Palace at the end of the street called “Merindad de Olite.” It has superb food at very reasonable prices and an excellent wine cellar from which you can order by the glass or half glass. The staff were very helpful with menu and wine suggestions.
While we were the first to arrive when Merindad de Olite opened for dinner, by the time we left the place was packed with locals who were regular customers.
Merindad de Olite is open for lunch and dinner 7 days a week. It’s located at C. Rua Juderia 11.
Have a great trip!

My vote is for the big city of Zaragoza.
We loved our 3 days there.

Zaragoza is hot now, but it isn’t a small town and it isn’t on the way from San Sebastián to Madrid.

My wife and I enjoy staying at Paradors and are staying at 10 later this year. For convenience we always pay for the breakfast buffet. By getting the breakfast we don’t need to try and find a place to eat and we don’t need to stop anyplace for lunch. We never get the half board. To be honest, I haven’t been overly impressed with most Paradors’ dinner menus.

The breakfast buffet is very good. There are cooked items as well as fresh fruits, cheeses, meats, yogurts, breads, etc. The meats and cheeses are sourced from the region the Parador is in, so are different at each Parador.

I will add that by joining the Paradors’ free Amigos program, you get a free breakfast for yourself and roommate the first time you reserve a room via its website. In addition, there’s an Amigos room price that is lower than the regular price, and, you get a free welcome beverage (beer, wine, soda, juice) every time you check into a Parador. Like the meats and cheeses at breakfast, the welcome wine you can get after checking in will be local.

For wine tasting we went to Bodega Cosecheros de Olite and Bodegas Vega del Castillo. With both you could choose the wine you wanted to sample and didn’t have to buy a flight of X samples. Each sample was less than 2€ when we were there and we were the only ones in the bodegas.

Olite it is! Thank you, everyone!

Kenko, thank you for sharing your experience and for the fantastic recommendation! I've added that restaurant to our plans.

jaimeelsabio, excellent tips for the paradors program and for bodegas to try. Much appreciated!