Planning a great road trip...

tgreen,
How did you find all the various properties? It is a challenge that I have not mastered to find interesting places to stay. I usually book hotels because my time abroad is rarely over 10 days - 2 weeks. Limited vacation time.
Enjoy your trip!

It takes some time and various references. I also like forums like this one. I had heard about the Pousadas and interestingly enough one group, Pestana Group handles 35 of these old abbeys, nunneries etc. (They have a discount if you book in January for any time of the year). Lisbon was tougher, but I went with a VRBO, so we can get a better ambiance of the city. Followed RS tour book in the south of Portugal and found a super option with kitchenette and sea view for a super great price. But then splurging in Coimbra with a very historical hotel and spa. We were super happy when we finally booked in the Douro Valley in a old country bed and breakfast.
Northern Spain is going to be super great, too.

Here are my top ways of researching a place.
1. Look for area you want to stay
2. Ask Tripadvisor and look at reviews and pictures (do not go with #1 place, unless you are in a very small town/city)
3. Look at guide books
4. Look at some youtube videos and any other reviews including forums.
5. Always try to book direct with the property. I rarely use booking.com.... I get a better deal or a better room and extras when booking direct.
Right now I'm looking for the most interesting things to see and do. I have a couple in the works. This takes quite a bit of time, but I think I'm finding some good things. Then I never book so full a schedule so to be able to ask locals for recommendations. They are perhaps the best people to find good food and an excellent adventure.

In Lisbon, the Time Out Market is a fun visit with many, many cool restaurants. The Time Out magazine and Lisbon Lux are great websites for restaurants. If you stop in Porto, Taste Porto food tours are very good.
A great side trip in northern Spain is the Altamira cave museum. The small town of Getaria is a very picturesque place for a stop, if you aren’t already staying there.

To get the most useful suggestions on restaurants and day trips, you need to tell which route you are following (a list of the towns you're staying in).

thanks acravens...
Lisbon, Salema, Evora, Obidos, Coimbra, Douro Valley, Porto, Guimaraes....

Santiago de Compostela, Gijon, Pasai Donibane, Lourdes, Carcassion, Toulouse.

We will be also doing day trips from a number of these locations. Especially to Bilbao and to San Sebastian, And in the areas of southern france.

In Porto there is a wonderful B&B. It is The InPatio Guesthouse. Great location, great owners, great breakfasts, updated rooms. However, there are only five rooms, so book early.

Other possible side-trips from Pasai Donibane: Hondarribia and Zumaia-Getaria-Zarautz.

From Gijon: Oviedo

From Santiago de Compostela: Combarra, Cambados, Tui, Pontevedra to the south; A Coruna and Betanzos to the north.

From Guimaraes: Barcelos and Braga

From Porto, Douro Valley or Coimbra: Viseu

From Obidos: Batalha, Tomar, Sintra, Lisbon

Edited add: From Toulouse: Albi

thank you acraven... you are indeed a traveler!

Started 46 years ago! Still many places I haven't been in Europe alone; working on that, though.