We have booked flights into Lisbon for next summer. At $500 roundtrip, nonstop from Boston on Delta, we simply couldn't pass it up. We need some help with the planning of the Spain leg of the trip. We love road trips so do not mind driving. Our tentative plan is to do a loop up through Portugal and then back down through western Spain.
About us: We are very independent and fairly adventurous travelers in our 60's. We do not like crowds and big cities. Our priorities are good food and wine, meeting local people and finding those hidden, overlooked, and under appreciated gems. We always rent a car and try to stay off the beaten track. We are foodies but not food snobs... We would rather eat at a hole in the wall than a starred Michelin restaurant, although those are OK, too. :)
Unfortunately, because I teach, we are limited to travel in the summer... not ideal, but better than not at all. We generally plan our trips to be about three weeks give or take a few days. Our favorite stays have been at agriturismos and homeaway/airbnb rentals. We do not like resorts and being right on top of other people. We are frequent travelers to Mexico and our most recent European trips have been to Sicily, Italy, and France where we enjoyed soaking up the local culture in the more rural areas, with day trips to some of the more popular attractions.
Our current plan is to spend four nights in Tomar and four nights in the Douro Valley. We would like to see Santiago de Compostela, and were thinking three nights in this area. We are stumped on where to go in western Spain after that. We would like to do at least three or four nights in Segovia as our "city" stop. We are looking for small villages that pack a wallop in terms of food and culture. Guadalupe has caught my eye..... We would like to be able to either walk to dinner or eat at agriturismo so we don't have to worry about drinking and driving. I have both the Michelin green guide and Rick Steve's Spain. I have done hours of reading but am overwhelmed by all of the choices.
Any advice would be greatly appreciated.