I am trying to plan a 2 week trip to Spain and Portugal for the beginning of August. Neither my husband nor I have ever been. On our vacations we love to explore interesting towns and villages, soak up the culture and enjoy good food and wine. Last year we did Rome, Tuscany, Florence and Venice and loved the mix of city and small towns. We loved most of all driving around Tuscany and seeing all of the hillside villages and sittng at the cafes. The proposed itinerary for this trip is as follows:

Fly into Barcelona and spend 2 nights
Drive to San Sebastian and spend 4 nights with daytrips to Bibao, Santander (and welcome any other suggestions)
Overnight train from San Sebastian to Lisbon (arrive 10:00 am)
2 nights Lisbon (daytrip to Sintra)
Rent a car and drive to Algarve
3 nights Algarve
Drive back to Lisbon for our last night
Depart Lisbon back to US

Thanks to all for your feedback/suggestions

Sounds like a great plan. But Santander would be a very long day-trip from San Sebastián. I suggest you instead go to fabulous small towns/villages along the coast close to San Sebastián such as Hondarribia, Getaria, Zumaya or Lekeitio.

Instead of driving south to the Algarve, i would recommend driving north to Porto. Stop at Obidos and other small towns along the way. Then enjoy the wine and food in Porto for a few day/nights.

Have a great time out there

I would skip the Algarve. In addition to Obidos, after leaving Lisbon,I would include Evora and Coimbra,both very worthwhile stops.

I loved, loved, loved san sebastian! You got it all right by spending time in that area...Wonderful, charming!! Sounds like a great plan...When we drove from madrid to San Sebastian, we just stopped at various little towns we saw along the way...It was a great escape.